Terry
- 4 years ago
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Terry Gets It In The End free porn video
The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and some faceless guy was fucking the shit out of me.
I learned to dance and I loved the way my skirt flew up and exposed my panties but dancing like that wasn't the way I had to dance at the school mixers. I had to dance like a boy, which was easier because all you had to do was move a little and shuffle you're feet while the girl did all the fun stuff.
There was one girl that asked me to dance after seeing that I wasn't really into this whole “mixer” scene. She was a very good dancer and very pretty and I was astonished that she didn't have a dozen guys wanting to dance with her. We danced to a few songs and then sat together and talked when we finished. I didn't have much experience with girls but she was very easy to talk to.
“You're a good dancer, Cheryl,” I said.
“You're not so bad but you need to relax and feel the music. I think that you could really dance if you let yourself go.”
“But it's kind of embarrassing,” I told her.
“I'll tell you what. You dance the next song, and I mean really let go and I'll tell you something embarrassing about me.”
“Really? What could you have that's embarrassing?”
“Dance with me and I'll tell you. You're a nice guy, not like the others. All they want to do is get in your panties,” she said and laughed.
“What makes you think I don't want the same thing?
“You're different. I can feel it.”
“Oh?”
“Yes. Now come on and dance with me.”
We danced and I let myself go, using all the girlie moves I'd been doing in my room. Well, a lot of them anyway.
“I knew you had it in you,” she laughed as we sat down again.
“But doesn't it make me look gay?”
“So what if it does? You had more fun this time. Right?”
“Yea, I guess I did. So now tell me something embarrassing about you.”
“Okay,” she replied and leaned closer to me. “I'm not wearing anything under my dress. No bra, no panties, just me.”
“Really? Cool,” I replied and laughed.
We danced to a few more songs before leaving. I'd somehow worked up enough courage to ask her out for something to eat after the dance. Later, when I drove her back to her car we kissed, and I mean we really kissed -tongue and everything. We dated the entire senior year, going to movies, dances, dinner, and whatever.
Then one night, sitting in my car at the local make out spot, we were kissing and I let my hands do some roaming. I found her breasts and gently began teasing her nipples. Soon enough my hand was inside her blouse and directly on her nipples,
“That feels so good,” she moaned and ran her hand across the slight bulge in my pants.
Before I even realized it my lips had moved to her nipples and I was sucking and running my tongue all across them. While I was busy with her nipples she unbuckled my belt and open my pants.
She had me so worked up that I had forgotten I was wearing panties until she brought it to my attention.
“Nice panties,” she said as her hand slid beneath the satin.
“Huh? Oh damn,” I exclaimed just as her hand found my throbbing cock.
“I like it,” she grinned and leaned down to take my cock in her mouth.
I couldn't believe how good it felt. Her mouth was so hot and wet and her tongue was giving me fits. It didn't take long before I blasted my load. “Oh damn, Cheryl. I'm so sorry! I couldn't help myself!”
She smiled at me and said, “That's okay, Terry. I wanted it to happen. And when I found that you were wearing panties, I just had to do it.” Then she kissed me.
I could taste my cum on her mouth and it was very exciting. Of course, I'd tasted my own cum many times but this was more exciting.
After some maneuvering I had her laying back on the seat and her legs spread wide. I lifted her skirt and saw her bare pussy. I knew I couldn't fuck her, not that I really wanted to do that sort of thing but I could give her pleasure in the same manner in which she'd serviced me, so I bent down and kissed her, gently licking her.
“Oooo, Terry!” she moaned.
Her moans told me I was doing something right so I continued. I'd read where girls really liked the way other girls ate pussy because the were slow and gentle, so that the way I did it as well. While I licked her pussy and teased her clit my hands tormented her titties, twisting and pinching her hard nipples.
“Oh! Oh! Oooohhh, baby! Yyyesss! Damn you can eat pussy!”
Then she raised her hips and shook herself at me, cumming hard against my mouth and screaming loudly. At that moment a copious amount of her fluids blasted out, surprising me and her. I thought at first that she had pissed in my mouth but it didn't taste like piss. Yes, I had tasted piss after seeing images of others drinking it. I decided that since she had just cum, it must be the female equivalent of semen.
“Wow! I certainly wasn't expecting that!”
“So now we're even,” I laughed.
“Well you feel free to do it again whenever you like,” Cheryl giggled. “But promise me one thing. Promise me you'll keep on wearing panties.”
“Don't worry, I will. I promise.”
For the duration of the school year Cheryl and I continued our oral sexual assaults on one another whenever we could find the opportunity. She really liked me in panties, which, of course, I still wore every day.
And it was one afternoon in her bed when we were both naked that she saw my toe nails were painted.
“Mmm, panties and painted toe nails,” she smiled, “very sexy. What else do you do that's feminine?”
“I, um, I sometimes like to dress like a girl. You know, skirt, blouse, stockings, bra, the whole nine yards,” I blushed and awkwardly confessed.
“Really? Cool! I guess that explains why you haven't tried to fuck me, not that I'm complaining about what you are doing to me,” she laughed and kissed me deeply.
We talked on and on, and I eventually told her about some of the erotic fantasies I had when I was all dressed up. Cheryl seemed to be extremely interested in them and then confessed to me that she also had some fantasies going on when I was eating her, like me really being a girl going down on her. One thing lead to another and I was soon promising to dress up like a girl for her when we could find the time.
One week before graduation she drove to my house and I was waiting for her arrival in a pastel blue mini-skirt, white satin blouse, black stockings, garter belt, red satin panties, bra and heels. Not only was I dressed but I also had on makeup and wore painted finger and toe nails.
“Holy cow! You look great, Terry,” she said immediately upon seeing me. “You make a very pretty girl!” She took out her phone and took several pictures of me. She had me posing for her everywhere, living room, bedroom, kitchen, even outside in the back yard, and took pictures of me in all sorts of positions from nice to risque to even some that left no doubt that I was born male.
“This is really making me hot, Terry,” she gasped.
“Yeah, me too,” I laughed.
After that it wasn't long before we were in my bed and I was extremely busy licking her flooding pussy. Cheryl was completely naked and I was still mostly dressed. But being dressed made me act more like a girl, which drove her wild. I was persistent in my activities, eating her slowly but with more passion than I thought I possessed.
“Yes! Yyyesss! I'm cumming again. Oooohhh, Terry, I'm cumming! I'm cumming!” Cheryl screamed, driving her pussy harder and harder against my lips.
After about a million orgasms, she pushed me away and then pulled me up to lay beside her while she caught her breath.
“Oh damn, baby, you've got to dress up when you eat me next time. That was absolutely wonderful! Will you? Will you be my lesbian lover?”
“I can do that,” I replied.
“You're a real keeper, baby,” she mumbled as she drifted to sleep in my arms.
We slept like this for an hour or so and when we awoke it was almost time for my mother to arrive. Cheryl quickly pulled on her skirt and top and then began brushing her king brunette hair.
“Put your jeans and shoes on over your stockings, babe,” she said urgently. “I'll brush your hair while you wash off your makeup and take off your fingernail polish.”
As quickly as I could I did as she said and then slipped on a black t-shirt without even thinking about my bra. When Cheryl mentioned it I put on a leather vest to hide the telltale signs of my bra. We barely had enough time to get to the den and switch on the television before Mom arrived home from work.
“Hi kids,” she said as she swept through the room on her way to her own room to change.
“I think we could have been sitting here stark naked and she wouldn't have noticed,” Cheryl laughed and ran her hand over my crotch as she leaned in to give me a kiss.
Since Cheryl was staying for dinner we got up and began preparing the meal, something I had been doing quite often.
After she had the table set Cheryl said, “You'll make someone a good wife someday.”
“Wife? Do you think I'm gay or something?” I asked, trying to sound serious.
“You may not be gay, babe, but you're pretty damn close,” she replied with a laugh. “Not that it matters a whole hell of a lot to me whether you are or not. I love you just the way you are.”
“And I love you, too, Cheryl. By definition, doesn't that mean I'm not gay?”
“I believe the correct term is latent homosexual,” she replied.
“You've got to be kidding. Right?”
“No, I'm not. But even if you're as queer as a three dollar bill, I don't care, baby. You're kind, definitely gentle, sweet, romantic, considerate. In short, Terry, you're wonderful.”
Her compliments lessened the the impact of her earlier words, but in my heart, I knew she was right.
Mom appeared in her usual attire, which wasn't much, just a t-shirt and panties. We say and ate and talked for quite a while until it was time for Cheryl to go home.
I walked her to her car and we kissed for quite a while.
“After what you did this afternoon I can't just leave you high and dry,” she whispered and opened my jeans. After a short time she had my dick out and was sitting in her car sucking me while I stood beside the car. The open door shielded what she was doing from any car passing by. She was very good at what she was doing and had me moaning and groaning in no time.
“Oh Cheryl, that feels so damn good! Oh baby, you're gonna make me cum! Oh! Oh! Oh! Here it cums baby, I'm there! Oh fuck! Oh fuck!” The last few words were unintelligible because I was draining my balls into her greedy mouth.
When I was finished she stood and kissed me deeply, give me all the cum she had in her mouth, which I accepted and swallowed.
“I bet you wish that was another man's cum you just swallowed. You dream about that. Don't you, Terry.”
“Sometimes, yes,” I admitted.
“We'll work on that,” she giggled.
”Work on what?”
“We'll work on finding you a cock to suck.”
“Yeah? How about we work on finding a girl to eat your pussy?”
“After we find a man for you.”
“A man?”
“Of course. Now I can sort of break you in, you know, with a strap on dildo, but I really think you'd prefer a real man with a cock that cums in you.”
“You really want me to suck a man's cock?”
“You'll love it, baby. And then when you get fucked, well, you'll really accept your gay side more than ever.”
“Whatever you say,” I agreed dubiously.
Truthfully, what she said got me to thinking. I knew my fantasies were of a gay nature, so maybe that's what I really wanted. And there was also my obsession with crossdressing and my desire to look and act as feminine as I possibly could. There was also the fact that when I had the perfect opportunities to fuck Cheryl my cock had mysteriously lost all interest and went limp.
“Tomorrow we're going to put some things to the test. From what I've seen of you all dressed up, I think you can easily pass as a girl, that being said we're going to spend the entire day as girls. We'll do some shopping, eat lunch and maybe do some people watching. It'll be great!”
“Go out? In public? As a girl? I don't know about that.”
“Oh come on. It'll be so exciting!”
I had to admit that it would be very exciting, and it was something I'd secretly wanted to do for a long time.
“What if someone figures out I'm not a girl?”
“So what if they do? It's very doubtful anyone would, and if they did they wouldn't care one way or another. Most people are too busy with their own business to worry about whether or not that pretty girl is a guy.”
“Okay, I'll do it.”
“Cool! I've got a pair of silicon falsies at home. They're not real big but they have a little bit of weight to them so they'll move and feel like real boobs. I'll bring them over in the morning. So you just be dressed and ready to go around nine.”
“Don't worry, I'll be ready. Those falsies sound very nice. Thank you.”
Before going to bed I took a long bath, shaving my legs closely, before taking care of my pubic hair and my arm pits. Slipping into a pair of yellow bikini panties and my bathrobe, I left the bathroom and nearly bumped into my mother.
“Watch out, Terry,” she laughed.
“Oops! Sorry, Mom.” I knew if I just rushed around her and went up to my room she'd wonder what was wrong and question me all night. So instead I told a little of tomorrow's plans. “Cheryl and I are going to the mall tomorrow. She's picking me up around nine so I thought I'd get a jump on getting ready.”
“To the mall, huh? Well don't get too carried away,” she laughed.
“Oh no, just a couple of things,” I giggled, not telling her those things would probably be a skirt and blouse and maybe another pair of heels.
“Oh, be on the lookout for a new swimsuit. That old one of yours looks horrendous. You've had it for how many years? Four? Five? Anyway, get a new one. Here, take my credit card and use it for the swimsuit. And for Pete's sake, get a good looking one this time; something with some color to it."
“Okay, okay,” I answered, “How about if I look for hot pink?” I was wondering how I could pick out a male swimsuit while all dressed up. This was something, I decided, I'd have to talk to Cheryl about.
“Hot pink would look good on you,” she smiled. “It goes nice with your pink toenails.”
“Huh?” I looked down at my toes and realized they were still painted and I wasn't wearing anything to hide them.
“Honey,” Mom laughed, “did you honestly think I didn't know about you dressing like a girl when I'm not here? I've known for years. I knew when you were a little boy that you weren't like the rest. So you see, crossdressing isn't a surprise to me. The only thing I'm not sure about is whether or not you're gay.”
“Mom! I've never been with a guy!”
“Ah, but I'd be willing to bet that you would be with a man if the opportunity arose. And when you finally do it, and mark my words, you'll be dressed up like a girl.”
The blush in my face was enough answer for her. There was really nothing I could say.
“With all this being said, I'd like to see you dressed up. I think you'd make a prettier girl than you are as a nice looking boy. What I mean is, as a boy you look kind of fragile but I think that as a girl you'd be cute and petite.”
“Do you really think so, Mom. I mean Cheryl has said the same thing.”
“Has she seen you dressed?”
“Well, yes, she has.”
“And what did she say?”
“She really liked it,” I replied, excitement in my voice, “She took lots of pictures of me with her phone.”
“Oh? Phone pictures, huh? I'll tell you what. You have my credit card so go ahead and get a decent digital camera while you're out shopping.”
When I got up the next morning I was as nervous as a cat on a hot tin roof. Somehow I got my makeup on and my nails painted to match my toes. After slipping on a pair of white satin bikini panties and a bra, I looked in my closet for something to wear and decided on a baby blue sleeveless A-line dress with a scalloped hem. Before the dress I put on a pair of nude pantyhose and then slipped the dress over my head. I chose a pair of white sandals with ankle straps and three inch heels and strapped them onto my dainty feet. Finally I pulled out a greyish purse and loaded it with everything I might need during the day, extra lipstick, a compact with powder, my wallet with Mom's credit card, my debit card, driver's license, cash, keys, cell phone, and even a tampon. Now I was as ready as I'd ever be to go out and face the world.
Cheryl arrived and handed me two boxes which held the falsies she had bragged about. Taking them from their boxes, she helped me slide them into the cups of my bra. She was right, their weight did feel good and natural.
Twenty minutes after she arrived we were driving across town to a very nice mall. I had to admit that the walk from the house to her car had felt exhilarating. On the way I told her about my conversation with my mother the night before.
“So your Mom knows about your crossdressing and thinks you're probably gay, huh? Cool! Well that changes everything. I think we should get the camera first and I'll use it to document your first day out.”
She pulled into a huge electronics discount store and parked. “Ready, lover?”
“As ready as I'll ever be,” I grinned and opened the door.
We walked into the store and I felt like every eye was on me but I kept my head up high and walked as though nothing was out of the ordinary.
“Just walk like you own the place, Terry. No one is going to say a word,” Cheryl said encouragingly as we entered the store and walked down the main aisle.
By the time we reached the camera department I was feeling more at ease. No one had said or done anything out of the ordinary. In fact, I felt as though I'd been accepted as a real woman.
The camera we chose was pretty neat. You could set it to take any number of pictures automatically as well as taking videos. The memory card was huge but Cheryl insisted on buying a spare. We picked out the camera, a docking unit for downloading to a computer, spare memory card, a car charging unit, as well as a tripod. I gave the salesman the credit card and then signed the receipt. He took it all in stride and thanked us for shopping. My first venture into the real world as a girl had gone off without a hitch and my confidence soared. It had been lots of fun and I decided that even if they knew I was a guy in a dress they weren't going to say anything for fear of losing a sale.
Before leaving the parking lot Cheryl plugged in the camera to charge.
“So how do you feel about getting out, now that you've conquered the first time?” Cheryl asked as she began driving.
“I liked it,” I replied, “and it wasn't as awful as I thought it would be.”
“Then you're going to love going to the mall. In fact, I may have a surprise for you.”
“Oh? Well just keep it safe and sane,” I laughed.
Once we arrived at the mall and made our way inside, Cheryl began taking picture as we did some window shopping. She even had me stop and do some posing for her right in the middle of the mall. But as we moved along I became more and more comfortable to the point where I didn't even think about the way I was dressed. Everything seemed quite natural to me.
We went into one of the stores and Cheryl insisted that I try on a few dresses as well as some skirts and blouses. I did and modeled them for her and she took pictures. She even came into the dressing area and took pictures of me changing.
I was trying on swimsuits and she was still taking pictures of me changing and then modeling. I tried on several one piece suits and then she started handing me two piece ones. When I tried on a skimpy little bikini I fell in love with it, especially since it was hot pink. I decided that this is one I had to have. I looked forward to getting a tan in it and seeing the tan lines it would leave behind.
When we left that store I had three bags of goodies. We made our way to the food court where we ate lunch and did some people watching. At first I watched the girls and women walking past to learn more about how to carry myself. Then my eyes started wandering to the guys and was impressed be a few of the nice asses I saw walking by. I couldn't help but wonder about the size of their manhood and found myself getting a slight erection.
“Okay, girlfriend, let's get going. I need to go into 'Les Femme' and check on something with the boss.”
We had to go to the other end of the mall to get to the store she worked in. While she went and talked with her boss I was left in the lingerie department. Looking around I found the prettiest nighties and, of course I just had to have one. I picked one that had sheer black panels on the sides, back, and tummy with blue satin insets covering all the important places.
Cheryl returned and she was smiling. “Now for your surprise. The store needs another girl to help out in the shoe department. All you have to do is fill out an application and the job is yours. Well, after you interview with the boss. Of course, that means coming to work all dressed up. How do you feel about that, Terry? Do you think you can do it?”
“A job? As a girl? Dressing every day? Give me a second to think it over,” I answered. The thought of being able to dress up nicely on a daily basis appealed to me. Everything was turning up roses for me.
“Okay. Where do I need to go?”
“Come with me,” she said and lead me back into the offices.
I sat and filled out the application and handed it back to her. She took it and me, into another office where her boss was waiting.
“Cheryl tells me you're wanting a job and we have an opening in the shoe department. Do you think you can handle waiting on women, or sometimes men, and sometimes men dressed as women?”
“Yes sir, I can handle that.”
“So if a man in a dress comes in you can wait on him without laughing or making any rude remarks?”
“Yes sir.”
“That's probably the hardest part of the job. That and stocking the latest fashions on the shelves. We'll give you a try. The last girl in this position couldn't stand seeing a man in a dress and was quite rude to him. Here at 'Les Femme' we don't care who purchases our products and we treat everyone with respect. If you can do that then the job is yours. You'll find that crossdressers and transvestites make up a good portion of our customers.”
“I can do it, sir,” I replied without hesitation.
“Good. Now would you be able to start tomorrow?”
“Tomorrow? Yes sir.”
“Good. I'm going to start you off with the day shift. It's slower and will give you time to become acquainted with our products.”
“What time?”
“The shift starts at ten but you need to be here around nine or nine thirty and clock in as soon as you arrive.”
“I'll be here.”
“Oh, and as far as a dress code goes; skirts and dresses, always wear hosiery. Don't wear anything too short; mid thigh is acceptable. Look your best at all times and keep that lovely smile on your face.”
“Not a problem, sir.”
“Then welcome aboard and I hope you live up to the build up Cheryl gave you.”
“I will, sir.”
“One other thing. Don't call me sir. My name is Mark. We're all professionals here but I like to keep things on a personal basis. If you have any questions you can feel free to ask me, or Cheryl, or the floor supervisor, Dana.”
“Yes sir, er, Mark.”
The interview ended and I walked out to meet Cheryl, or rather hug her. I had a job as a girl and I had her to thank.
“You need to buy a couple of pairs of shoes so you don't wear the same thing every day,” she said and lead me to the shoe department.
I preferred the open toe shoes and the girl waiting on me found some very good ones. Since I was now employed there I got a nice discount. Of course, Cheryl took plenty of pictures of me trying on shoes and walking around in them. They were all nice and I found two pair that I liked more than the others.
By the time we left the mall it was nearly four in the afternoon. I'd had the most wonderful time being out as a girl and I had Cheryl to thank for the entire experience. When we got to my house Mom was already home and she insisted that I model everything I'd bought.
“You really look lovely, Terry. I knew you would. I've always thought you'd be a wonderful daughter and now I'm sure of it. And you tell me you have a job as well? That's wonderful!”
When I modeled the bikini I thought her eyes might pop out.
“Oooo, that's excellent, baby. You have some curves. Not much of a girlish figure but a little bit and I know how we can help that along if you're willing.”
“How?”
“We can start you on some female hormones. Not only will that enhance your figure but it'll make your boobs grow. How would you like to have your own boobies and not have to wear those falsies?”
“That would be great!”
“Just to make you aware. Any curves and boob growth you get out of them is not reversible, so you need to make sure you want to do it. I mean, if you change your mind and decide you'd rather be a guy you'll have breasts to contend with.”
“No, I'd prefer to go ahead and have boobs,” I replied.
“I kind of thought you'd say that,” she laughed. “And you, Cheryl. What do you think about your boyfriend growing breasts and being more like a girl?”
“I think it would be wonderful!” Cheryl exclaimed. “Now if only those hormones could take care of that other little thing, she'd be perfect.”
“But they can't do that,” Mom said, “only a surgical procedure can take care of that.”
“That's okay, Mom. Sorry Cheryl. But I think I'll hang on to my little guy for a while longer,” I laughed.
“Understandable, baby. You should enjoy your dick while you can. Don't you think so, Cheryl?”
“I'm willing,” she laughed, “and I think Terry knows it. Unfortunately the only time I know of when he get's hard is when I'm sucking him.”
“Probably because he's more interested in men doing him than him doing a girl.”
“Mom!”
“Oh come on, Terry! You know in your heart that you're gay and would rather have a man ramming his cock in your ass or down your throat than you would have your cock in Cheryl's pussy.”
“But that's okay, baby,” Cheryl added, “you keep me very well satisfied in another way.”
“Hell, maybe I'm a lesbian,” I laughed.
After the modeling and discussion we ate dinner and it did feel weird to be sitting at the table dressed as a girl and talking to my mother and girlfriend.
“I'll pick you up in the morning, baby,” Cheryl said after kissing me goodbye.
Getting ready for work the next morning was a rather different experience since my mother hadn't left for her office yet. Walking around the house in bra and panties felt just a little embarrassing for a while but soon enough I grew accustomed to it. Mom left and I had the house to myself to finish getting ready for work. Today I wore a pale blue skirt and rose blouse over my garter belt and sun tan stockings. The falsies felt very natural today as they warmed to my body.
When Cheryl arrived I picked up my purse and calmly walked to her car.
“Good morning, lover,” she said as I climbed in.
“Good morning,” I returned and leaned over to give her a kiss. “I'm really excited about starting to work. You have no idea how much I've wanted to have a job as a girl, and now I do, thanks to you.”
“Well, you work your ass off and you'll move on up the ladder. Learn everything you can about every department you work in and you'll be on the fast track.”
I began by learning how to ring up a sale and where the inventory was kept, spending more time running back and forth finding shoes than actually waiting on customers. But by the end of my shift I knew where everything was and the easiest way to get them. By the end of the fourth day I could handle anything in the shoe department.
Somehow Cheryl and I managed to get the same days off and she was at my house bright and early. I met her at the door in a nightie and robe but neither of us remained fully dressed very long, she was totally naked and I was down to just my nightie.
We rolled over my bed, hands searching and caressing. I went down on her but she stopped me after only one orgasm.
“I'm gonna take your cherry, baby,” she cooed, reaching into her purse.
I'm not sure how she got it in there, but she pulled out a large strop on dildo and a tube of lubricant. She stood and strapped the harness onto her, leaving her standing before me with an immense erection.
“Suck my cock, baby,” she commanded, slowly stroking the dildo. “Kiss it, lick it, take it in your mouth and suck it!”
I did exactly as she instructed and soon I was sucking her just like I had fantasized about doing with a real dick. My own dick grew hard as I sucked on hers and pretended it was a real man I was sucking. Then I discovered that when I moved the dildo back forth or pushed and pulled on it that Cheryl moaned and gasped like I was licking her clit.
“Yeah, baby, suck my cock! Mmm, it feels so good! Damn, you're a good cocksucker! Keep it up! Keep it up! Fuck, you're gonna make me cum!”
Placing my hands on her hips I moved my mouth back and forth, up and down, grinding the dildo against her clit. Then, much to my astonishment, Cheryl began bucking harder against me, driving the dildo deeper into my mouth. She was cumming, and cumming very hard. I was really amazed when a thick gooey cream began spurting into my mouth, the taste and consistency very close to my own cum. So much flooded into me that I was forced to swallow it or choke.
“Yeah! Oh yeah! Oh fuck yeah!” Cheryl squealed, holding my head onto the dildo while she squeezed the bulb and sent more and more of her cum into me.
She pulled back and squeezed it one more time, sending a thick rope of fluid onto my face.
“Mmm, baby, you can suck my cock anytime. Don't you dare touch your clit, baby. Let me reload this thing and then I'm going to fuck your cute little boy pussy.”
“Do you really think that big thing is going to fit?” I laughed.
“Of course I do, and I'll bet you'll be begging for more!”
While I waited for her to return I thought about how good it felt to be sucking a dick. Okay it was a dildo, but the action was the same, and I'd induced an orgasm. I wondered how good it was going to feel when she unloaded into my asshole. Somehow I knew it would feel wonderful and I didn't care if I had an orgasm or not.
“Okay, bitch, get on your back and spread your legs!” Cheryl commanded when she returned.
Picking up the lubricant, she smeared a large amount on the dildo and then even more in and around my tight little hole. “Just relax, baby, everything will be just fine. You're going to love this.”
Cheryl placed a pillow beneath me, tilting my ass toward her and crept closer. Holding the dildo, she aimed it at my boy pussy and moved into position.
I felt her pressing against me and did my best to relax.
“It's going to hurt a little at first, so just try and relax,” she said, pushing a little harder.
Then I felt my asshole beginning to open wide to accept the dildo and it hurt like hell, but I wanted this to happen.
“Oh yeah, baby, take it all,” Cheryl groaned as she pushed inside me.
Suddenly the head of the dildo was in me and the rest of the shaft slid in easily, making me gasp aloud.
“Now I'm going to fuck you real good. You're my bitch now.”
“Oh yyyesss, baby, fuck your bitch!” I moaned as she pulled back. “Ooohhh, yeah! Fuck me good!”
For the next twenty minutes the only sounds in the room were of her steadily slapping against me and my moans and groans of pure lusty pleasure. It was hard for me to believe that a dildo in my ass could feel so wonderful and I wondered how a real man's cock would feel as it pounded me.
“Oh yes, fuck me! Damn it feels so good. Fuck me harder! Faster! Oh! Oh! Yyyesss!”
My body shuddered as a wave of pleasure crashed over me and yet I knew I hadn't yet discharged any fluids. Cheryl continued to hammer my ass, going faster and faster.
“Oh fuck! Oh fuck! Here it comes, baby! I'm gonna cum! I'm gonna cum!” Cheryl declared, slamming into me harder and harder until she began shaking and quaking.
“Do it! Cum in me! Of fuck, baby, I need it! Ooohhh, I'm cumming!” I squealed and felt my dick spitting onto the bed below me.
Cheryl squeezed the bulb and sent a river of fluid into me, filling me completely and overflowing around the dildo to stream over my balls and onto the bed.
Pushing deeper inside me, Cheryl rolled me onto my back and the collapsed on top of me, her dick still inside me and her lips crushing against mine. Without even thinking my legs went up and around her waist, locking at the heels, and holding her inside as we kissed deeply.
“That was fantastic,” I moaned.
“I knew you'd like it,” she smiled, “and you'll like it even more the next time. You're my bitch now and I'm going to fuck you very regularly.”
“I'm yours to use, lover.”
“Yes, you are.”
And she did. Over the next three months Cheryl fucked me with her big, squirting dildo at every opportunity. We even had sex in her office at work on several occasions. My little hole had become accustom to her entries and it no longer hurt when she took me. I did, however, have a problem with her fake cum oozing out of me and into my panties while at work.
I began seeing a psychiatrist and he decided that I was very sincere in my desire to become feminine. So after three months he started me on hormones replacement therapy. For two months I saw very little or no change in my body and began to wonder about this treatment. However, I did notice that my emotions were becoming more like a girl, tearing up in some movies, having a great desire to eat Cheryl's lovely pussy, really wanting to have sex with a man, and so on. It was in the fourth month that I noticed my titties growing more tender and puffy. Both my mother and Cheryl told me this was normal for a girl. There was also some redistribution of fatty tissue as in my butt growing and filling out my clothes better than before.
Once, when Cheryl was fucking me in the missionary position she remarked at how my little titties bounced and moved as she slammed into me.
Today, as my one and a half year anniversary of working at the store came around I no longer had to rely on the falsies to fell out my bra. My titties had grown to a little over a B cup. Of course, my dick had shrunk somewhat and it was harder for me to masturbate, which only fueled my desire to have sex with a man.
Cheryl brought in another girl one night when it was time for a good fucking. The girl, Anna, enjoyed making me cum when she used the dildo on me and Cheryl like watching me cum, even taking pictures of my dick spurting out a thin stream of cum. Once they finished fucking me, Anna and Cheryl had sex together while I watched. It was wonderful watching two beautiful girl giving each other so much pleasure.
By now I was living full time as a woman but I was still longing for the feel of a real man using me. When Cheryl's parents died in an automobile accident, she moved out and bought a house of her own and I moved in with her, though we maintained separate bedrooms. Anna was a very frequent over night guest and she soon discovered the joys of making me give her a blow job before one of them fucked me. I was also allowed to eat Anna and found that her pussy tasted more tangy than Cheryl's, but I liked it anyway.
Then one day at work Cheryl called me into her office.
“Your work has been exemplary, Terry, so I'm going to give you a promotion. I still want you to be in charge of sales because I've seen how you handle the men who come in and buy things for themselves or maybe their wives. You always treated them with respect, and our sales of larger items has sky rocketed.”
“Thank you. I know how scared I was when we first went shopping so I try to make it easier for them.”
“And you've done an excellent job. I want you to train another girl to do what you've been doing. She's a bit older but you'll find the two of you have quite a bit in common. Namely, she's also a transvestite. Her name is Kelly and she starts tomorrow so you'll need to drive yourself to work because she doesn't come on until the night shift and you'll be working late with her.”
“Not a problem,” I said confidently.
When Kelly came to work the next day she was a whirlwind, learning everything as fast as I could teach her. Like me she was extremely glad to have a job as a girl that she couldn't contain herself. She knew she needed to better than just good, she had to excel. She was pretty and very respectful of the customers, especially the men. Kelly was a couple of inches taller than me with bright red hair and green eyes, a very pleasing figure, and an outgoing personality. She would show them exactly what they asked for and then suggest something that might look better on them, man or woman, depending on their height and figure. In just three days of training I was confident that she could handle her shift without any trouble at all.
I went to Cheryl's office and told her how well Kelly was doing, letting her know I was prepared to turn her loose.
“That's great, Terry. I knew you'd have her ready in no time at all. So next week a real girl is coming to work in the lingerie department and I want you to train her as well.”
“Okie-dokey, boss lady,” I grinned.
“But for now I want you to take off all your clothes because I'm kind of horny.”
I wasted little time removing my clothes and soon I was naked and ready for whatever she wanted. Cheryl took off her clothes and strapped on one of her dildos.
“Okay baby, suck me.”
I fell to my knees and started working on her dick, moving it this way and that in such a manner that I knew the base would be rubbing her clit. I heard the door behind her desk open and close but I couldn't see who had come in. Since Cheryl wasn't concerned about this I just kept on sucking on her cock.
“Oh, there you are,” Cheryl said, her voice moaning with pleasure.
“So this is Terry who you've been talking about,” a man's deep voice said.
Being naked and my mouth full of dildo, I blushed a little but Cheryl continued fucking my face so I didn't worry about it.
“Yes, this is the girl I've been talking about. You can see that she loves sucking cock, and you can imagine what she does when she get's fucked. Ooohhh fuck, I'm gonna cum, Terry. Here it comes! Oh shit! Oh shit!”
With that she began spurting into my mouth and I had to start swallowing.
“Yes, I can see that she loves sucking your dildo, but let's see how she handles the real thing,” he said and moved beside her.
“Okay Terry,” Cheryl said, “here's the real thing. Are you ready for it?”
“I hope so. I've dreamed about sucking a real cock for a long time,” I replied and smiled brightly.
“This is my big brother, Jeff, and he wants you to give him a blow job.”
“Yes, ma'am. Thank you!” I replied and moved to begin kissing and licking my very first real cock. This also gave me something new to play with, balls. So I kissed them as well.
Reaching down, Jeff began playing with my titties, driving me insane with his touch. When I took his cock into my mouth I could immediately tell the difference. I could feel the life and power throbbing in him and I loved the way it felt when he slid over my lips while my tongue played all around him.
“Damn, she's good!”
“She's been practicing on me for over a year.”
“Mmm, she certainly learned a lot. And her mouth is so fucking hot and soft. Yeah, baby, suck my dick. Oh yeah, it feels great. Oh baby, I'm gonna fill your mouth with the real stuff and I bet you'll really love it!”
“Will you please?” I asked, holding his dick in my hand as I asked. That was when I noticed that my own dick, small as it had become, was as hard as a rock. But for now all I wanted to do was suck his cock and then I'd worry about my own erection.
I took him back into my mouth and began moving up and down his shaft, thinking only about the prize at the end of the rainbow. Jeff's cock was thicker than Cheryl's dildo but not quite as long, but still a good eight inches.
I kept my lips locked on his cock, even while he was thrusting into my mouth. The only thing I could think of was getting him to cum. I wanted it, no I needed it so badly.
Cheryl stood to the side and took quite a few pictures of her brother fucking my face.
“Come on, Jeff, don't hold back, give her a mouth full.”
“I will! Oh fuck yeah, I'm almost there. Get ready, Terry! Fuck I'm gonna cum in your mouth!”
I was almost there. This is what I'd been working for. I felt his cock thicken and then he was doing it. Jeff was actually spewing his load of creamy hot cum into my mouth. He didn't cum as much as Cheryl's dildo so it was easier to swallow and taste at the same time. His cum tasted wonderful but I reluctantly had to swallow it. Now I truly was a cocksucker and I felt so proud.
Jeff helped me to my feet and gave me a hug.
“I'll jack you off if you'll catch it and lick your hands clean. Will you do that?” Jeff asked as his large hand began slowly stroking my small dick.
“Yes sir, I certainly will.”
“My, my, this is just about the smallest dick I've ever seen. It's so cute!,” he grinned, stoking me while my head lay on his chest.
“I'm gonna cum!” I squealed after just a few strokes and moved my hand to catch my sperm. There wasn't much and I dutifully began licking my hand clean. And all the while Cheryl took more pictures.
“Your Mom would be so proud of you, Terry,” she laughed and then swatted my bare ass.
“Yes, she's raised a good cocksucker,” I replied.
“Terry, tomorrow I want you to report to my office. We're going to see how you like man cum in your sexy little boy pussy.”
“Yes, sir.”
“And to save some time, wear stockings so you can just take off your panties and be ready.”
“Yes, sir. I'm looking forward to it!”
The next morning I reported to Jeff's office as he had instructed and he proceeded to fuck my ass so much harder than Cheryl ever had. My little dick spewed much sooner than his big one and I had to clean my cum off him desk. The rest of the day I could feel his cum oozing out of my asshole and drenching my panties but I felt more alive after actually being fucked by a man than ever before. From that day on I reported directly to Jeff and either sucked his dick or gave up my ass. I became his personal assistant and often traveled with him.
That was five years ago and I still live with Cheryl and Anna and they still fuck me with the dildo but I spend quite a bit of time at Jeff's house, spending several nights a week, almost living with him. Sometimes he brings a friend over and I gladly service them both.
Oh, and the psychiatrist has told me that I'm a very good candidate for sexual reassignment surgery but as long as Jeff and his friends like me as I am, I'll just keep my little dick where it is. I get all the cock I want and I feel like I'm the luckiest girl in the world.
As for Kelly, I trained her to take my place and also found out what her cum tastes like, and she got a good sampling of mine.
I learned to dance and I loved the way my skirt flew up and exposed my panties but dancing like that wasn't the way I had to dance at the school mixers. I had to dance like a boy, which was easier because all you had to do was move a little and shuffle you're feet while the girl did all the fun stuff.
There was one girl that asked me to dance after seeing that I wasn't really into this whole “mixer” scene. She was a very good dancer and very pretty and I was astonished that she didn't have a dozen guys wanting to dance with her. We danced to a few songs and then sat together and talked when we finished. I didn't have much experience with girls but she was very easy to talk to.
“You're a good dancer, Cheryl,” I said.
“You're not so bad but you need to relax and feel the music. I think that you could really dance if you let yourself go.”
“But it's kind of embarrassing,” I told her.
“I'll tell you what. You dance the next song, and I mean really let go and I'll tell you something embarrassing about me.”
“Really? What could you have that's embarrassing?”
“Dance with me and I'll tell you. You're a nice guy, not like the others. All they want to do is get in your panties,” she said and laughed.
“What makes you think I don't want the same thing?
“You're different. I can feel it.”
“Oh?”
“Yes. Now come on and dance with me.”
We danced and I let myself go, using all the girlie moves I'd been doing in my room. Well, a lot of them anyway.
“I knew you had it in you,” she laughed as we sat down again.
“But doesn't it make me look gay?”
“So what if it does? You had more fun this time. Right?”
“Yea, I guess I did. So now tell me something embarrassing about you.”
“Okay,” she replied and leaned closer to me. “I'm not wearing anything under my dress. No bra, no panties, just me.”
“Really? Cool,” I replied and laughed.
We danced to a few more songs before leaving. I'd somehow worked up enough courage to ask her out for something to eat after the dance. Later, when I drove her back to her car we kissed, and I mean we really kissed -tongue and everything. We dated the entire senior year, going to movies, dances, dinner, and whatever.
Then one night, sitting in my car at the local make out spot, we were kissing and I let my hands do some roaming. I found her breasts and gently began teasing her nipples. Soon enough my hand was inside her blouse and directly on her nipples,
“That feels so good,” she moaned and ran her hand across the slight bulge in my pants.
Before I even realized it my lips had moved to her nipples and I was sucking and running my tongue all across them. While I was busy with her nipples she unbuckled my belt and open my pants.
She had me so worked up that I had forgotten I was wearing panties until she brought it to my attention.
“Nice panties,” she said as her hand slid beneath the satin.
“Huh? Oh damn,” I exclaimed just as her hand found my throbbing cock.
“I like it,” she grinned and leaned down to take my cock in her mouth.
I couldn't believe how good it felt. Her mouth was so hot and wet and her tongue was giving me fits. It didn't take long before I blasted my load. “Oh damn, Cheryl. I'm so sorry! I couldn't help myself!”
She smiled at me and said, “That's okay, Terry. I wanted it to happen. And when I found that you were wearing panties, I just had to do it.” Then she kissed me.
I could taste my cum on her mouth and it was very exciting. Of course, I'd tasted my own cum many times but this was more exciting.
After some maneuvering I had her laying back on the seat and her legs spread wide. I lifted her skirt and saw her bare pussy. I knew I couldn't fuck her, not that I really wanted to do that sort of thing but I could give her pleasure in the same manner in which she'd serviced me, so I bent down and kissed her, gently licking her.
“Oooo, Terry!” she moaned.
Her moans told me I was doing something right so I continued. I'd read where girls really liked the way other girls ate pussy because the were slow and gentle, so that the way I did it as well. While I licked her pussy and teased her clit my hands tormented her titties, twisting and pinching her hard nipples.
“Oh! Oh! Oooohhh, baby! Yyyesss! Damn you can eat pussy!”
Then she raised her hips and shook herself at me, cumming hard against my mouth and screaming loudly. At that moment a copious amount of her fluids blasted out, surprising me and her. I thought at first that she had pissed in my mouth but it didn't taste like piss. Yes, I had tasted piss after seeing images of others drinking it. I decided that since she had just cum, it must be the female equivalent of semen.
“Wow! I certainly wasn't expecting that!”
“So now we're even,” I laughed.
“Well you feel free to do it again whenever you like,” Cheryl giggled. “But promise me one thing. Promise me you'll keep on wearing panties.”
“Don't worry, I will. I promise.”
For the duration of the school year Cheryl and I continued our oral sexual assaults on one another whenever we could find the opportunity. She really liked me in panties, which, of course, I still wore every day.
And it was one afternoon in her bed when we were both naked that she saw my toe nails were painted.
“Mmm, panties and painted toe nails,” she smiled, “very sexy. What else do you do that's feminine?”
“I, um, I sometimes like to dress like a girl. You know, skirt, blouse, stockings, bra, the whole nine yards,” I blushed and awkwardly confessed.
“Really? Cool! I guess that explains why you haven't tried to fuck me, not that I'm complaining about what you are doing to me,” she laughed and kissed me deeply.
We talked on and on, and I eventually told her about some of the erotic fantasies I had when I was all dressed up. Cheryl seemed to be extremely interested in them and then confessed to me that she also had some fantasies going on when I was eating her, like me really being a girl going down on her. One thing lead to another and I was soon promising to dress up like a girl for her when we could find the time.
One week before graduation she drove to my house and I was waiting for her arrival in a pastel blue mini-skirt, white satin blouse, black stockings, garter belt, red satin panties, bra and heels. Not only was I dressed but I also had on makeup and wore painted finger and toe nails.
“Holy cow! You look great, Terry,” she said immediately upon seeing me. “You make a very pretty girl!” She took out her phone and took several pictures of me. She had me posing for her everywhere, living room, bedroom, kitchen, even outside in the back yard, and took pictures of me in all sorts of positions from nice to risque to even some that left no doubt that I was born male.
“This is really making me hot, Terry,” she gasped.
“Yeah, me too,” I laughed.
After that it wasn't long before we were in my bed and I was extremely busy licking her flooding pussy. Cheryl was completely naked and I was still mostly dressed. But being dressed made me act more like a girl, which drove her wild. I was persistent in my activities, eating her slowly but with more passion than I thought I possessed.
“Yes! Yyyesss! I'm cumming again. Oooohhh, Terry, I'm cumming! I'm cumming!” Cheryl screamed, driving her pussy harder and harder against my lips.
After about a million orgasms, she pushed me away and then pulled me up to lay beside her while she caught her breath.
“Oh damn, baby, you've got to dress up when you eat me next time. That was absolutely wonderful! Will you? Will you be my lesbian lover?”
“I can do that,” I replied.
“You're a real keeper, baby,” she mumbled as she drifted to sleep in my arms.
We slept like this for an hour or so and when we awoke it was almost time for my mother to arrive. Cheryl quickly pulled on her skirt and top and then began brushing her king brunette hair.
“Put your jeans and shoes on over your stockings, babe,” she said urgently. “I'll brush your hair while you wash off your makeup and take off your fingernail polish.”
As quickly as I could I did as she said and then slipped on a black t-shirt without even thinking about my bra. When Cheryl mentioned it I put on a leather vest to hide the telltale signs of my bra. We barely had enough time to get to the den and switch on the television before Mom arrived home from work.
“Hi kids,” she said as she swept through the room on her way to her own room to change.
“I think we could have been sitting here stark naked and she wouldn't have noticed,” Cheryl laughed and ran her hand over my crotch as she leaned in to give me a kiss.
Since Cheryl was staying for dinner we got up and began preparing the meal, something I had been doing quite often.
After she had the table set Cheryl said, “You'll make someone a good wife someday.”
“Wife? Do you think I'm gay or something?” I asked, trying to sound serious.
“You may not be gay, babe, but you're pretty damn close,” she replied with a laugh. “Not that it matters a whole hell of a lot to me whether you are or not. I love you just the way you are.”
“And I love you, too, Cheryl. By definition, doesn't that mean I'm not gay?”
“I believe the correct term is latent homosexual,” she replied.
“You've got to be kidding. Right?”
“No, I'm not. But even if you're as queer as a three dollar bill, I don't care, baby. You're kind, definitely gentle, sweet, romantic, considerate. In short, Terry, you're wonderful.”
Her compliments lessened the the impact of her earlier words, but in my heart, I knew she was right.
Mom appeared in her usual attire, which wasn't much, just a t-shirt and panties. We say and ate and talked for quite a while until it was time for Cheryl to go home.
I walked her to her car and we kissed for quite a while.
“After what you did this afternoon I can't just leave you high and dry,” she whispered and opened my jeans. After a short time she had my dick out and was sitting in her car sucking me while I stood beside the car. The open door shielded what she was doing from any car passing by. She was very good at what she was doing and had me moaning and groaning in no time.
“Oh Cheryl, that feels so damn good! Oh baby, you're gonna make me cum! Oh! Oh! Oh! Here it cums baby, I'm there! Oh fuck! Oh fuck!” The last few words were unintelligible because I was draining my balls into her greedy mouth.
When I was finished she stood and kissed me deeply, give me all the cum she had in her mouth, which I accepted and swallowed.
“I bet you wish that was another man's cum you just swallowed. You dream about that. Don't you, Terry.”
“Sometimes, yes,” I admitted.
“We'll work on that,” she giggled.
”Work on what?”
“We'll work on finding you a cock to suck.”
“Yeah? How about we work on finding a girl to eat your pussy?”
“After we find a man for you.”
“A man?”
“Of course. Now I can sort of break you in, you know, with a strap on dildo, but I really think you'd prefer a real man with a cock that cums in you.”
“You really want me to suck a man's cock?”
“You'll love it, baby. And then when you get fucked, well, you'll really accept your gay side more than ever.”
“Whatever you say,” I agreed dubiously.
Truthfully, what she said got me to thinking. I knew my fantasies were of a gay nature, so maybe that's what I really wanted. And there was also my obsession with crossdressing and my desire to look and act as feminine as I possibly could. There was also the fact that when I had the perfect opportunities to fuck Cheryl my cock had mysteriously lost all interest and went limp.
“Tomorrow we're going to put some things to the test. From what I've seen of you all dressed up, I think you can easily pass as a girl, that being said we're going to spend the entire day as girls. We'll do some shopping, eat lunch and maybe do some people watching. It'll be great!”
“Go out? In public? As a girl? I don't know about that.”
“Oh come on. It'll be so exciting!”
I had to admit that it would be very exciting, and it was something I'd secretly wanted to do for a long time.
“What if someone figures out I'm not a girl?”
“So what if they do? It's very doubtful anyone would, and if they did they wouldn't care one way or another. Most people are too busy with their own business to worry about whether or not that pretty girl is a guy.”
“Okay, I'll do it.”
“Cool! I've got a pair of silicon falsies at home. They're not real big but they have a little bit of weight to them so they'll move and feel like real boobs. I'll bring them over in the morning. So you just be dressed and ready to go around nine.”
“Don't worry, I'll be ready. Those falsies sound very nice. Thank you.”
Before going to bed I took a long bath, shaving my legs closely, before taking care of my pubic hair and my arm pits. Slipping into a pair of yellow bikini panties and my bathrobe, I left the bathroom and nearly bumped into my mother.
“Watch out, Terry,” she laughed.
“Oops! Sorry, Mom.” I knew if I just rushed around her and went up to my room she'd wonder what was wrong and question me all night. So instead I told a little of tomorrow's plans. “Cheryl and I are going to the mall tomorrow. She's picking me up around nine so I thought I'd get a jump on getting ready.”
“To the mall, huh? Well don't get too carried away,” she laughed.
“Oh no, just a couple of things,” I giggled, not telling her those things would probably be a skirt and blouse and maybe another pair of heels.
“Oh, be on the lookout for a new swimsuit. That old one of yours looks horrendous. You've had it for how many years? Four? Five? Anyway, get a new one. Here, take my credit card and use it for the swimsuit. And for Pete's sake, get a good looking one this time; something with some color to it."
“Okay, okay,” I answered, “How about if I look for hot pink?” I was wondering how I could pick out a male swimsuit while all dressed up. This was something, I decided, I'd have to talk to Cheryl about.
“Hot pink would look good on you,” she smiled. “It goes nice with your pink toenails.”
“Huh?” I looked down at my toes and realized they were still painted and I wasn't wearing anything to hide them.
“Honey,” Mom laughed, “did you honestly think I didn't know about you dressing like a girl when I'm not here? I've known for years. I knew when you were a little boy that you weren't like the rest. So you see, crossdressing isn't a surprise to me. The only thing I'm not sure about is whether or not you're gay.”
“Mom! I've never been with a guy!”
“Ah, but I'd be willing to bet that you would be with a man if the opportunity arose. And when you finally do it, and mark my words, you'll be dressed up like a girl.”
The blush in my face was enough answer for her. There was really nothing I could say.
“With all this being said, I'd like to see you dressed up. I think you'd make a prettier girl than you are as a nice looking boy. What I mean is, as a boy you look kind of fragile but I think that as a girl you'd be cute and petite.”
“Do you really think so, Mom. I mean Cheryl has said the same thing.”
“Has she seen you dressed?”
“Well, yes, she has.”
“And what did she say?”
“She really liked it,” I replied, excitement in my voice, “She took lots of pictures of me with her phone.”
“Oh? Phone pictures, huh? I'll tell you what. You have my credit card so go ahead and get a decent digital camera while you're out shopping.”
When I got up the next morning I was as nervous as a cat on a hot tin roof. Somehow I got my makeup on and my nails painted to match my toes. After slipping on a pair of white satin bikini panties and a bra, I looked in my closet for something to wear and decided on a baby blue sleeveless A-line dress with a scalloped hem. Before the dress I put on a pair of nude pantyhose and then slipped the dress over my head. I chose a pair of white sandals with ankle straps and three inch heels and strapped them onto my dainty feet. Finally I pulled out a greyish purse and loaded it with everything I might need during the day, extra lipstick, a compact with powder, my wallet with Mom's credit card, my debit card, driver's license, cash, keys, cell phone, and even a tampon. Now I was as ready as I'd ever be to go out and face the world.
Cheryl arrived and handed me two boxes which held the falsies she had bragged about. Taking them from their boxes, she helped me slide them into the cups of my bra. She was right, their weight did feel good and natural.
Twenty minutes after she arrived we were driving across town to a very nice mall. I had to admit that the walk from the house to her car had felt exhilarating. On the way I told her about my conversation with my mother the night before.
“So your Mom knows about your crossdressing and thinks you're probably gay, huh? Cool! Well that changes everything. I think we should get the camera first and I'll use it to document your first day out.”
She pulled into a huge electronics discount store and parked. “Ready, lover?”
“As ready as I'll ever be,” I grinned and opened the door.
We walked into the store and I felt like every eye was on me but I kept my head up high and walked as though nothing was out of the ordinary.
“Just walk like you own the place, Terry. No one is going to say a word,” Cheryl said encouragingly as we entered the store and walked down the main aisle.
By the time we reached the camera department I was feeling more at ease. No one had said or done anything out of the ordinary. In fact, I felt as though I'd been accepted as a real woman.
The camera we chose was pretty neat. You could set it to take any number of pictures automatically as well as taking videos. The memory card was huge but Cheryl insisted on buying a spare. We picked out the camera, a docking unit for downloading to a computer, spare memory card, a car charging unit, as well as a tripod. I gave the salesman the credit card and then signed the receipt. He took it all in stride and thanked us for shopping. My first venture into the real world as a girl had gone off without a hitch and my confidence soared. It had been lots of fun and I decided that even if they knew I was a guy in a dress they weren't going to say anything for fear of losing a sale.
Before leaving the parking lot Cheryl plugged in the camera to charge.
“So how do you feel about getting out, now that you've conquered the first time?” Cheryl asked as she began driving.
“I liked it,” I replied, “and it wasn't as awful as I thought it would be.”
“Then you're going to love going to the mall. In fact, I may have a surprise for you.”
“Oh? Well just keep it safe and sane,” I laughed.
Once we arrived at the mall and made our way inside, Cheryl began taking picture as we did some window shopping. She even had me stop and do some posing for her right in the middle of the mall. But as we moved along I became more and more comfortable to the point where I didn't even think about the way I was dressed. Everything seemed quite natural to me.
We went into one of the stores and Cheryl insisted that I try on a few dresses as well as some skirts and blouses. I did and modeled them for her and she took pictures. She even came into the dressing area and took pictures of me changing.
I was trying on swimsuits and she was still taking pictures of me changing and then modeling. I tried on several one piece suits and then she started handing me two piece ones. When I tried on a skimpy little bikini I fell in love with it, especially since it was hot pink. I decided that this is one I had to have. I looked forward to getting a tan in it and seeing the tan lines it would leave behind.
When we left that store I had three bags of goodies. We made our way to the food court where we ate lunch and did some people watching. At first I watched the girls and women walking past to learn more about how to carry myself. Then my eyes started wandering to the guys and was impressed be a few of the nice asses I saw walking by. I couldn't help but wonder about the size of their manhood and found myself getting a slight erection.
“Okay, girlfriend, let's get going. I need to go into 'Les Femme' and check on something with the boss.”
We had to go to the other end of the mall to get to the store she worked in. While she went and talked with her boss I was left in the lingerie department. Looking around I found the prettiest nighties and, of course I just had to have one. I picked one that had sheer black panels on the sides, back, and tummy with blue satin insets covering all the important places.
Cheryl returned and she was smiling. “Now for your surprise. The store needs another girl to help out in the shoe department. All you have to do is fill out an application and the job is yours. Well, after you interview with the boss. Of course, that means coming to work all dressed up. How do you feel about that, Terry? Do you think you can do it?”
“A job? As a girl? Dressing every day? Give me a second to think it over,” I answered. The thought of being able to dress up nicely on a daily basis appealed to me. Everything was turning up roses for me.
“Okay. Where do I need to go?”
“Come with me,” she said and lead me back into the offices.
I sat and filled out the application and handed it back to her. She took it and me, into another office where her boss was waiting.
“Cheryl tells me you're wanting a job and we have an opening in the shoe department. Do you think you can handle waiting on women, or sometimes men, and sometimes men dressed as women?”
“Yes sir, I can handle that.”
“So if a man in a dress comes in you can wait on him without laughing or making any rude remarks?”
“Yes sir.”
“That's probably the hardest part of the job. That and stocking the latest fashions on the shelves. We'll give you a try. The last girl in this position couldn't stand seeing a man in a dress and was quite rude to him. Here at 'Les Femme' we don't care who purchases our products and we treat everyone with respect. If you can do that then the job is yours. You'll find that crossdressers and transvestites make up a good portion of our customers.”
“I can do it, sir,” I replied without hesitation.
“Good. Now would you be able to start tomorrow?”
“Tomorrow? Yes sir.”
“Good. I'm going to start you off with the day shift. It's slower and will give you time to become acquainted with our products.”
“What time?”
“The shift starts at ten but you need to be here around nine or nine thirty and clock in as soon as you arrive.”
“I'll be here.”
“Oh, and as far as a dress code goes; skirts and dresses, always wear hosiery. Don't wear anything too short; mid thigh is acceptable. Look your best at all times and keep that lovely smile on your face.”
“Not a problem, sir.”
“Then welcome aboard and I hope you live up to the build up Cheryl gave you.”
“I will, sir.”
“One other thing. Don't call me sir. My name is Mark. We're all professionals here but I like to keep things on a personal basis. If you have any questions you can feel free to ask me, or Cheryl, or the floor supervisor, Dana.”
“Yes sir, er, Mark.”
The interview ended and I walked out to meet Cheryl, or rather hug her. I had a job as a girl and I had her to thank.
“You need to buy a couple of pairs of shoes so you don't wear the same thing every day,” she said and lead me to the shoe department.
I preferred the open toe shoes and the girl waiting on me found some very good ones. Since I was now employed there I got a nice discount. Of course, Cheryl took plenty of pictures of me trying on shoes and walking around in them. They were all nice and I found two pair that I liked more than the others.
By the time we left the mall it was nearly four in the afternoon. I'd had the most wonderful time being out as a girl and I had Cheryl to thank for the entire experience. When we got to my house Mom was already home and she insisted that I model everything I'd bought.
“You really look lovely, Terry. I knew you would. I've always thought you'd be a wonderful daughter and now I'm sure of it. And you tell me you have a job as well? That's wonderful!”
When I modeled the bikini I thought her eyes might pop out.
“Oooo, that's excellent, baby. You have some curves. Not much of a girlish figure but a little bit and I know how we can help that along if you're willing.”
“How?”
“We can start you on some female hormones. Not only will that enhance your figure but it'll make your boobs grow. How would you like to have your own boobies and not have to wear those falsies?”
“That would be great!”
“Just to make you aware. Any curves and boob growth you get out of them is not reversible, so you need to make sure you want to do it. I mean, if you change your mind and decide you'd rather be a guy you'll have breasts to contend with.”
“No, I'd prefer to go ahead and have boobs,” I replied.
“I kind of thought you'd say that,” she laughed. “And you, Cheryl. What do you think about your boyfriend growing breasts and being more like a girl?”
“I think it would be wonderful!” Cheryl exclaimed. “Now if only those hormones could take care of that other little thing, she'd be perfect.”
“But they can't do that,” Mom said, “only a surgical procedure can take care of that.”
“That's okay, Mom. Sorry Cheryl. But I think I'll hang on to my little guy for a while longer,” I laughed.
“Understandable, baby. You should enjoy your dick while you can. Don't you think so, Cheryl?”
“I'm willing,” she laughed, “and I think Terry knows it. Unfortunately the only time I know of when he get's hard is when I'm sucking him.”
“Probably because he's more interested in men doing him than him doing a girl.”
“Mom!”
“Oh come on, Terry! You know in your heart that you're gay and would rather have a man ramming his cock in your ass or down your throat than you would have your cock in Cheryl's pussy.”
“But that's okay, baby,” Cheryl added, “you keep me very well satisfied in another way.”
“Hell, maybe I'm a lesbian,” I laughed.
After the modeling and discussion we ate dinner and it did feel weird to be sitting at the table dressed as a girl and talking to my mother and girlfriend.
“I'll pick you up in the morning, baby,” Cheryl said after kissing me goodbye.
Getting ready for work the next morning was a rather different experience since my mother hadn't left for her office yet. Walking around the house in bra and panties felt just a little embarrassing for a while but soon enough I grew accustomed to it. Mom left and I had the house to myself to finish getting ready for work. Today I wore a pale blue skirt and rose blouse over my garter belt and sun tan stockings. The falsies felt very natural today as they warmed to my body.
When Cheryl arrived I picked up my purse and calmly walked to her car.
“Good morning, lover,” she said as I climbed in.
“Good morning,” I returned and leaned over to give her a kiss. “I'm really excited about starting to work. You have no idea how much I've wanted to have a job as a girl, and now I do, thanks to you.”
“Well, you work your ass off and you'll move on up the ladder. Learn everything you can about every department you work in and you'll be on the fast track.”
I began by learning how to ring up a sale and where the inventory was kept, spending more time running back and forth finding shoes than actually waiting on customers. But by the end of my shift I knew where everything was and the easiest way to get them. By the end of the fourth day I could handle anything in the shoe department.
Somehow Cheryl and I managed to get the same days off and she was at my house bright and early. I met her at the door in a nightie and robe but neither of us remained fully dressed very long, she was totally naked and I was down to just my nightie.
We rolled over my bed, hands searching and caressing. I went down on her but she stopped me after only one orgasm.
“I'm gonna take your cherry, baby,” she cooed, reaching into her purse.
I'm not sure how she got it in there, but she pulled out a large strop on dildo and a tube of lubricant. She stood and strapped the harness onto her, leaving her standing before me with an immense erection.
“Suck my cock, baby,” she commanded, slowly stroking the dildo. “Kiss it, lick it, take it in your mouth and suck it!”
I did exactly as she instructed and soon I was sucking her just like I had fantasized about doing with a real dick. My own dick grew hard as I sucked on hers and pretended it was a real man I was sucking. Then I discovered that when I moved the dildo back forth or pushed and pulled on it that Cheryl moaned and gasped like I was licking her clit.
“Yeah, baby, suck my cock! Mmm, it feels so good! Damn, you're a good cocksucker! Keep it up! Keep it up! Fuck, you're gonna make me cum!”
Placing my hands on her hips I moved my mouth back and forth, up and down, grinding the dildo against her clit. Then, much to my astonishment, Cheryl began bucking harder against me, driving the dildo deeper into my mouth. She was cumming, and cumming very hard. I was really amazed when a thick gooey cream began spurting into my mouth, the taste and consistency very close to my own cum. So much flooded into me that I was forced to swallow it or choke.
“Yeah! Oh yeah! Oh fuck yeah!” Cheryl squealed, holding my head onto the dildo while she squeezed the bulb and sent more and more of her cum into me.
She pulled back and squeezed it one more time, sending a thick rope of fluid onto my face.
“Mmm, baby, you can suck my cock anytime. Don't you dare touch your clit, baby. Let me reload this thing and then I'm going to fuck your cute little boy pussy.”
“Do you really think that big thing is going to fit?” I laughed.
“Of course I do, and I'll bet you'll be begging for more!”
While I waited for her to return I thought about how good it felt to be sucking a dick. Okay it was a dildo, but the action was the same, and I'd induced an orgasm. I wondered how good it was going to feel when she unloaded into my asshole. Somehow I knew it would feel wonderful and I didn't care if I had an orgasm or not.
“Okay, bitch, get on your back and spread your legs!” Cheryl commanded when she returned.
Picking up the lubricant, she smeared a large amount on the dildo and then even more in and around my tight little hole. “Just relax, baby, everything will be just fine. You're going to love this.”
Cheryl placed a pillow beneath me, tilting my ass toward her and crept closer. Holding the dildo, she aimed it at my boy pussy and moved into position.
I felt her pressing against me and did my best to relax.
“It's going to hurt a little at first, so just try and relax,” she said, pushing a little harder.
Then I felt my asshole beginning to open wide to accept the dildo and it hurt like hell, but I wanted this to happen.
“Oh yeah, baby, take it all,” Cheryl groaned as she pushed inside me.
Suddenly the head of the dildo was in me and the rest of the shaft slid in easily, making me gasp aloud.
“Now I'm going to fuck you real good. You're my bitch now.”
“Oh yyyesss, baby, fuck your bitch!” I moaned as she pulled back. “Ooohhh, yeah! Fuck me good!”
For the next twenty minutes the only sounds in the room were of her steadily slapping against me and my moans and groans of pure lusty pleasure. It was hard for me to believe that a dildo in my ass could feel so wonderful and I wondered how a real man's cock would feel as it pounded me.
“Oh yes, fuck me! Damn it feels so good. Fuck me harder! Faster! Oh! Oh! Yyyesss!”
My body shuddered as a wave of pleasure crashed over me and yet I knew I hadn't yet discharged any fluids. Cheryl continued to hammer my ass, going faster and faster.
“Oh fuck! Oh fuck! Here it comes, baby! I'm gonna cum! I'm gonna cum!” Cheryl declared, slamming into me harder and harder until she began shaking and quaking.
“Do it! Cum in me! Of fuck, baby, I need it! Ooohhh, I'm cumming!” I squealed and felt my dick spitting onto the bed below me.
Cheryl squeezed the bulb and sent a river of fluid into me, filling me completely and overflowing around the dildo to stream over my balls and onto the bed.
Pushing deeper inside me, Cheryl rolled me onto my back and the collapsed on top of me, her dick still inside me and her lips crushing against mine. Without even thinking my legs went up and around her waist, locking at the heels, and holding her inside as we kissed deeply.
“That was fantastic,” I moaned.
“I knew you'd like it,” she smiled, “and you'll like it even more the next time. You're my bitch now and I'm going to fuck you very regularly.”
“I'm yours to use, lover.”
“Yes, you are.”
And she did. Over the next three months Cheryl fucked me with her big, squirting dildo at every opportunity. We even had sex in her office at work on several occasions. My little hole had become accustom to her entries and it no longer hurt when she took me. I did, however, have a problem with her fake cum oozing out of me and into my panties while at work.
I began seeing a psychiatrist and he decided that I was very sincere in my desire to become feminine. So after three months he started me on hormones replacement therapy. For two months I saw very little or no change in my body and began to wonder about this treatment. However, I did notice that my emotions were becoming more like a girl, tearing up in some movies, having a great desire to eat Cheryl's lovely pussy, really wanting to have sex with a man, and so on. It was in the fourth month that I noticed my titties growing more tender and puffy. Both my mother and Cheryl told me this was normal for a girl. There was also some redistribution of fatty tissue as in my butt growing and filling out my clothes better than before.
Once, when Cheryl was fucking me in the missionary position she remarked at how my little titties bounced and moved as she slammed into me.
Today, as my one and a half year anniversary of working at the store came around I no longer had to rely on the falsies to fell out my bra. My titties had grown to a little over a B cup. Of course, my dick had shrunk somewhat and it was harder for me to masturbate, which only fueled my desire to have sex with a man.
Cheryl brought in another girl one night when it was time for a good fucking. The girl, Anna, enjoyed making me cum when she used the dildo on me and Cheryl like watching me cum, even taking pictures of my dick spurting out a thin stream of cum. Once they finished fucking me, Anna and Cheryl had sex together while I watched. It was wonderful watching two beautiful girl giving each other so much pleasure.
By now I was living full time as a woman but I was still longing for the feel of a real man using me. When Cheryl's parents died in an automobile accident, she moved out and bought a house of her own and I moved in with her, though we maintained separate bedrooms. Anna was a very frequent over night guest and she soon discovered the joys of making me give her a blow job before one of them fucked me. I was also allowed to eat Anna and found that her pussy tasted more tangy than Cheryl's, but I liked it anyway.
Then one day at work Cheryl called me into her office.
“Your work has been exemplary, Terry, so I'm going to give you a promotion. I still want you to be in charge of sales because I've seen how you handle the men who come in and buy things for themselves or maybe their wives. You always treated them with respect, and our sales of larger items has sky rocketed.”
“Thank you. I know how scared I was when we first went shopping so I try to make it easier for them.”
“And you've done an excellent job. I want you to train another girl to do what you've been doing. She's a bit older but you'll find the two of you have quite a bit in common. Namely, she's also a transvestite. Her name is Kelly and she starts tomorrow so you'll need to drive yourself to work because she doesn't come on until the night shift and you'll be working late with her.”
“Not a problem,” I said confidently.
When Kelly came to work the next day she was a whirlwind, learning everything as fast as I could teach her. Like me she was extremely glad to have a job as a girl that she couldn't contain herself. She knew she needed to better than just good, she had to excel. She was pretty and very respectful of the customers, especially the men. Kelly was a couple of inches taller than me with bright red hair and green eyes, a very pleasing figure, and an outgoing personality. She would show them exactly what they asked for and then suggest something that might look better on them, man or woman, depending on their height and figure. In just three days of training I was confident that she could handle her shift without any trouble at all.
I went to Cheryl's office and told her how well Kelly was doing, letting her know I was prepared to turn her loose.
“That's great, Terry. I knew you'd have her ready in no time at all. So next week a real girl is coming to work in the lingerie department and I want you to train her as well.”
“Okie-dokey, boss lady,” I grinned.
“But for now I want you to take off all your clothes because I'm kind of horny.”
I wasted little time removing my clothes and soon I was naked and ready for whatever she wanted. Cheryl took off her clothes and strapped on one of her dildos.
“Okay baby, suck me.”
I fell to my knees and started working on her dick, moving it this way and that in such a manner that I knew the base would be rubbing her clit. I heard the door behind her desk open and close but I couldn't see who had come in. Since Cheryl wasn't concerned about this I just kept on sucking on her cock.
“Oh, there you are,” Cheryl said, her voice moaning with pleasure.
“So this is Terry who you've been talking about,” a man's deep voice said.
Being naked and my mouth full of dildo, I blushed a little but Cheryl continued fucking my face so I didn't worry about it.
“Yes, this is the girl I've been talking about. You can see that she loves sucking cock, and you can imagine what she does when she get's fucked. Ooohhh fuck, I'm gonna cum, Terry. Here it comes! Oh shit! Oh shit!”
With that she began spurting into my mouth and I had to start swallowing.
“Yes, I can see that she loves sucking your dildo, but let's see how she handles the real thing,” he said and moved beside her.
“Okay Terry,” Cheryl said, “here's the real thing. Are you ready for it?”
“I hope so. I've dreamed about sucking a real cock for a long time,” I replied and smiled brightly.
“This is my big brother, Jeff, and he wants you to give him a blow job.”
“Yes, ma'am. Thank you!” I replied and moved to begin kissing and licking my very first real cock. This also gave me something new to play with, balls. So I kissed them as well.
Reaching down, Jeff began playing with my titties, driving me insane with his touch. When I took his cock into my mouth I could immediately tell the difference. I could feel the life and power throbbing in him and I loved the way it felt when he slid over my lips while my tongue played all around him.
“Damn, she's good!”
“She's been practicing on me for over a year.”
“Mmm, she certainly learned a lot. And her mouth is so fucking hot and soft. Yeah, baby, suck my dick. Oh yeah, it feels great. Oh baby, I'm gonna fill your mouth with the real stuff and I bet you'll really love it!”
“Will you please?” I asked, holding his dick in my hand as I asked. That was when I noticed that my own dick, small as it had become, was as hard as a rock. But for now all I wanted to do was suck his cock and then I'd worry about my own erection.
I took him back into my mouth and began moving up and down his shaft, thinking only about the prize at the end of the rainbow. Jeff's cock was thicker than Cheryl's dildo but not quite as long, but still a good eight inches.
I kept my lips locked on his cock, even while he was thrusting into my mouth. The only thing I could think of was getting him to cum. I wanted it, no I needed it so badly.
Cheryl stood to the side and took quite a few pictures of her brother fucking my face.
“Come on, Jeff, don't hold back, give her a mouth full.”
“I will! Oh fuck yeah, I'm almost there. Get ready, Terry! Fuck I'm gonna cum in your mouth!”
I was almost there. This is what I'd been working for. I felt his cock thicken and then he was doing it. Jeff was actually spewing his load of creamy hot cum into my mouth. He didn't cum as much as Cheryl's dildo so it was easier to swallow and taste at the same time. His cum tasted wonderful but I reluctantly had to swallow it. Now I truly was a cocksucker and I felt so proud.
Jeff helped me to my feet and gave me a hug.
“I'll jack you off if you'll catch it and lick your hands clean. Will you do that?” Jeff asked as his large hand began slowly stroking my small dick.
“Yes sir, I certainly will.”
“My, my, this is just about the smallest dick I've ever seen. It's so cute!,” he grinned, stoking me while my head lay on his chest.
“I'm gonna cum!” I squealed after just a few strokes and moved my hand to catch my sperm. There wasn't much and I dutifully began licking my hand clean. And all the while Cheryl took more pictures.
“Your Mom would be so proud of you, Terry,” she laughed and then swatted my bare ass.
“Yes, she's raised a good cocksucker,” I replied.
“Terry, tomorrow I want you to report to my office. We're going to see how you like man cum in your sexy little boy pussy.”
“Yes, sir.”
“And to save some time, wear stockings so you can just take off your panties and be ready.”
“Yes, sir. I'm looking forward to it!”
The next morning I reported to Jeff's office as he had instructed and he proceeded to fuck my ass so much harder than Cheryl ever had. My little dick spewed much sooner than his big one and I had to clean my cum off him desk. The rest of the day I could feel his cum oozing out of my asshole and drenching my panties but I felt more alive after actually being fucked by a man than ever before. From that day on I reported directly to Jeff and either sucked his dick or gave up my ass. I became his personal assistant and often traveled with him.
That was five years ago and I still live with Cheryl and Anna and they still fuck me with the dildo but I spend quite a bit of time at Jeff's house, spending several nights a week, almost living with him. Sometimes he brings a friend over and I gladly service them both.
Oh, and the psychiatrist has told me that I'm a very good candidate for sexual reassignment surgery but as long as Jeff and his friends like me as I am, I'll just keep my little dick where it is. I get all the cock I want and I feel like I'm the luckiest girl in the world.
As for Kelly, I trained her to take my place and also found out what her cum tastes like, and she got a good sampling of mine.
Jerri
- 28.01.2023
- 49
- 0
- Category:
- Crossdressing
