Sharon goes dogging
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Sharon Goes The Distance free porn video
When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or even while she fucked me with her large strap on dildo. We posted these photos on a free, picture sharing website. Both of us got hotter than hell when we read the comments people left.
I climbed out of bed and silently padded to the bathroom to begin my transformation. First came a long, hot bath which included shaving my legs silky smooth and then my armpits followed by my pubic area. Donna had insisted that I keep these areas shaved at all times, which pretty much left me hairless all over. Since we'd had my facial hair removed permanently via electrolysis I no longer had to worry about that area. Next I painstakingly applied my makeup to achieve the look I preferred. Finally I took out the breast forms and applied the adhesive to them and my natural breasts so they wouldn't slip out of place. I loved how they felt and looked, moving with me when I walked or bent over. With this out of the way I slipped on a natural hair wig and brushed it back to style before I sat on the counter and painted my nails, both finger and toe. I normally kept my toe nails painted since they were out of sight when I was at work. Actually I wore panties to work daily and usually stockings as well.
Today would be the first time Donna had ever taken me out in public and I needed everything to be perfect. When I finished and gazed into the mirror all I could see was a pretty red haired woman looking back at me. Well, that is, until my gaze looked at the dick between my legs but that would be taken care of later when I had it tucked away.
Ready for whatever challenges faced me, I slipped into a long, soft, pink robe and went to the kitchen for a morning cup of coffee. Of course, I would have to make it first. It was just about ready when Donna came in.
“Good morning, sexy,” she said as she entered the kitchen and I poured her a steaming cup.
“Good morning, lover,” I smiled and sat at the table with her. I never ceased to be amazed when I looked at my lovely wife.
“Are you ready to make your public debut?”
“As ready as I'll ever be,” I replied, wondering if I was really ready.
“You'll love the freedom of going out as a woman, babe. Besides, you know you want to. Hell, you've always wanted to go out all dressed up.”
“Maybe in my fantasies,” I laughed. “But this is different. I mean, it's broad daylight.”
“That's okay. Believe me, no one will ever know. You've got the walk down pat, and your voice is perfect. Today we're a couple of women going shopping at the mall.”
The mall meant I would really be on public display so I had better be able to pass as a woman without a hitch.
“If you're a good girl I'll have a big surprise for you tonight.”
That usually meant one thing. She'd be fucking me with her strap on dildo again, an act I had immediately loved from the first time we'd had sex like this.
“Oooo, sounds like I better be a good girl,” I laughed and kissed her.
I went back to the bedroom and found that she had already laid out my clothes for the day. I'd be wearing a knee length, loose fitting yellow dress, a white thong, garter belt, nude stockings, and four inch open toe white heels. Nothing to draw any undue attention to me, for which I was thankful. As far as accessories went, Donna had chosen a gold anklet, a pretty heart shaped necklace, a dainty wrist watch, a nice pearl ring to replace my wedding band, dangling earrings, and a charm bracelet for me to wear.
“Well, how do I look?” I asked after I was ready.
Naturally it hadn't taken Donna nearly as long to get ready so she was waiting for me to make my appearance.
“Sexy!” she exclaimed. “I think you'll be drawing more attention than me finally.”
“No way. You're way too pretty and so damn sexy,” I replied, grinning at her.
“Don't be too sure of that. Pretty soon you'll have to fight off the men with a stick.”
“Yea, right. A man in a dress compared to a sexy little vixen like yourself? Don't be silly.”
“Babe, you don't even come close to looking like a man in a dress anymore. You're a hot woman and you really need to act the part.”
“Okay, I guess you want me to flirt a little while I'm at it,” I said, teasingly.
“Wouldn't hurt my feelings if you did. As a matter of fact, you flirt with a man and so will I. After all, we'll be at the mall, so what could happen?”
“Good point,” I laughed and picked up my purse after I made sure I had everything I needed in it.
Donna had drilled me at length on what I should carry in my purse. I had lipstick, a compact, tissues, a tampon, wallet, house and car key, cell phone, credit cards and cash. I was as ready to go as I'd ever be.
Donna drove in case we happened to get pulled over for some reason, which was the most logical course. Beside, I was still too nervous to even think about driving. We arrived at the mall and walked a long way to get to the entrance. I think Donna did this on purpose so I could be seen by more and more people. Much to my relief, most of the people were busy concentrating on their shopping and didn't give me more than a cursory glance.
Inside the mall Donna and I did a lot of window shopping, slowly moving through the mall. She did, however, steer us into a high end lingerie store where we picked out a very sexy emerald green and black teddy with lace insets for me and a lovely purple one for her.
“You'll look very hot in that little number, Sharon,” she told me. “And yes, I want you to wear it tonight. In fact, I want you to change into it as soon as we get home so I can take some pictures of your sexy ass.”
I really enjoyed posing for Donna and it actually helped me become more feminine and sexy even though the only one who'd every actually seen me, until today, was my wife. Of course, this wasn't counting the thousands who saw my pictures on line. There were hundreds of pictures of me in various states of dress and undress, even some with Donna fucking me with her strap on and some where I was fucking her with my own dick before cleaning her pussy, and all the while dressed as Sharon.
From the lingerie store we moved on to a shoe store where Donna picked out a pair of sandals with five inch stiletto heels and straps that traveled up to my calves. I thought they were a bit over the top but she insisted that I get them.
“After all, baby, they'll make you look like such a whore with that short, skin tight dress I bought for you,” Donna laughed in front of the salesman.
“You're right,” I giggled, “they certainly will.”
“Will you help me with these?” I asked the salesman.
“Of course,” he answered and knelt to help me get them on and laced properly. “Lovely feet.”
“Thank you,” I answered and smiled sweetly. I have to admit that his hands on my feet felt wonderful, sending an electrical charge up my spine. For the first time in my life I looked at another man with more than a passing interest. I actually found myself wondering what he might be like in bed.
“You do that so well,” I smiled and wondered if this was flirting according to Donna.
“Lot's of practice,” he replied and smiled up at me.
Then it struck me that he had the most beautiful bright blue eyes that seemed to see into your soul and sparkled when he smiled. I could almost feel myself melting under his gaze.
Once the shoes were secured to me, he helped me stand so I could walk around the store and check out the way they felt. I don't think I meant to do it, and honestly don't know why I did it, but I know I put a little extra wiggle in my walk.
Donna met me at the far end of the store and commented with a giggle, “Keep it up, Sharon, and this guy will want to fuck you in the back room.”
“Keep up what?”
“That sexy walk. You're practically begging him to fuck you,” she replied and laughed aloud.
“What? No I'm not!” I protested with a little too much vigor.
We bought the shoes and I wore them out of the store, liking the way they looked and felt, and really liking the way they made me feel. After some more window shopping we wound up at the food court for a cool drink and a slice of pizza.
I needed to go to the little girl's room so I excused myself for a few minutes. When I came back Donna was talking to a man I recognized as our neighbor. I held back for a minute hoping he would go away but it became obvious he was in no hurry so I sucked it up and returned to our table.
“Oh Sharon, this is our neighbor, Sean. Sean, this is Sharon.”
“Very pleased to meet you,” he smiled and held out his hand.
“My pleasure,” I replied and took his hand. If he recognized me his face and manners certainly didn't show it.
Sean stayed with us and talked to Donna for several minutes about his plans to landscape his backyard. Occasionally I made some comment on what he was doing but never really got into the conversation. In fact, I was looking at our neighbor in a different light, thinking of him more as a potential partner in sex, than anything to do with landscaping.
Why was I even having thoughts like this? Was it because I was dressed like, and acting like, a woman? Sure, lots of men had some sort of masturbation fantasies about being a woman and being taken by a man, but I never had, at least until now. Now I couldn't keep from thinking how it would feel to have his hard cock in my mouth or even up my ass instead of the role playing Donna and I did with her strap on.
“Sure, I'll come over and take a look at it. No promises that I can fix the problem. It's a shame David isn't more of a handy man.”
“No, it's a shame he isn't more of a man,” she replied. “Especially in the bedroom.”
“Oops. That's one problem you'll have to figure out on your own, honey,” Sean said and smiled.
“Why is that?”
“Honestly, and I mean total honesty, you'd be safe sleeping in my bed totally naked. Sorry, but you're not exactly my type.”
“I see and understand perfectly,” Donna answered when she realized he really wasn't into women. “But you will take a look at the leak?”
“Of course I will. Um, will David understand if he comes home and finds me alone with you?”
“You won't be. Sharon will be there with us.”
“Good. I'd hate for there to be some misunderstanding.”
Donna laughed and then replied, “There won't be. Everything is crystal clear.”
“Good. I'll try and get over there this afternoon and take a look.”
“Thank you. I've been after David for months to do something but I'm afraid he'd make it worse and plumbers are so expensive.”
“I know. That's one of the reasons I learned how to fix things myself,” he laughed and got up to leave.
Once he was out of hearing range I said to Donna, “What's the idea of telling him something as intimate as the bedroom? Were you trying to get laid?”
“The thought crossed my mind. Besides you flirted with the man at the shoe store. I'm just showing you how a woman goes about flirting.”
“Yea, yea. You know, if I did something like that either you'd get mad or the guy might expect me to follow through,” I said and then grinned.
“And what would Sharon do if a man wanted her?” Donna asked a little too innocently.
“Probably run away screaming,” I laughed, hoping to avoid the subject.
“I think otherwise, I think Sharon would get on her knees and suck his cock like a good little girl.”
“Huh? Why do you say that?”
“That's what I would do,” she laughed. “Besides, I think it would be so hot to see you do something like that, or maybe something more. You know how much you enjoy it when I fuck you're ass pussy. Just imagine what it would be like with a real dick that pumped you full of hot cream.”
“Do you really want to see me with a man?” I asked, already knowing the answer. Donna and I and talked about this very thing on several occasions and I knew just how hot it made her.
“I think it would be so hot,” she replied quickly. “And besides, how many times have you said you wanted to see me with another woman or very well hung man? Or for that matter, you've even suggested a gang bang.”
“Okay, okay, I get the picture,” I sighed. It was true, I'd expressed my fantasies of seeing her with other men and women, so I suppose turn about was fair play. Donna obviously wanted me to have sex with a man, but could I actually do it? Could I suck a dick? I wasn't sure if I could or not. Did I want to suck a dick? I had to admit that the idea was quite intriguing.
“I will if you will,” she said and smiled mischievously.
“Okay, you're on,” I answered suddenly.
“I knew you'd say that. Are you ready to take this crossdressing thing to the next level? Are you ready to find out what it really feels like to be a woman?”
Looking her in the eyes I answered, “I'm willing to give it a try.”
“I have a feeling you'll love it,” she laughed.
“Hell, I don't even have a clue how to find a man who'll fuck another man in a dress.”
“Don't worry, I think I know someone who'd do you in a heartbeat.”
“Okay then, I'll leave it up to you to find me a guy to have sex with,” I laughed, “and a woman for yourself. I know a man who would give up his left nut to take you to bed.”
“And you'll be there watching while wearing a dress.”
That was a new wrinkle but even though that would mean letting a friend know I was a crossdresser I was okay with it.
“Okay.”
“And when he finishes you'll eat my pussy and his cum.”
“Okay.”
“And when another woman and I have sex you'll be in a dress.”
“Yes,” I agreed. For some reason I couldn't fathom, the thought of sucking a cock, or even taking a hard cock up my ass, was somehow appealing.
“Well, okay then. I guess the first thing you need to do is learn how to suck a dick and I know just how to teach you,” Donna laughed. “You see, I've been doing quite a bit of research on this subject because I knew you were going to agree.”
“You did? How?”
“You were way too easy to get dressed in women's clothes and never once objected to the makeup, or going out in public. You were way too quick learning how to walk and talk and do your makeup. In my opinion, this is something you've always wanted to do, whether you knew it or not.”
I didn't answer her because I was thinking back to some of my masturbation fantasies when I was growing up. More often than not I imagined that some guy was either fucking me or I was sucking his cock and getting a mouthful of cum.
“Ready?” Donna asked.
“Yes, I guess I am.”
We left the mall and I noticed I had more spring in my step than usual and Donna was in a much happier mood than I'd seen her in for a while. Was this because I was going to learn how to suck a cock or because she was going to have sex with other men?
Soon enough we were in the car and she was driving away with a destination in mind.
“You have to remember to lick and kiss a man's dick from one end to the other but pay special attention to the head. They really love it when you tongue the rim around the head,” she was saying as she drove. “Oh, if he cums in your mouth be sure to swallow. They really like that. You can taste his seed of course, and I recommend that. Hell, you'll love tasting other guy's cum. We already know you like your own. But then there's always the one that wants to cum on your face, so be prepared for that also. Some men also like being verbal, calling you all sorts of names like slut, whore, cocksucker, and in your case, fagot, queer or sissy. Don't be offended, it's just a way that they get more stimulated.”
“Okay, I can understand the name calling.”
“Are you ready for your lessons to begin?”
Suddenly I began looking forward to learning how to suck a man's dick. “Yes. Yes, I believe I am.”
“Good,” she answered and pulled into an adult book store we'd been to on several occasions where we had purchased her strap on as well as quite a few movies, some of which had been those with transvestites, a few were girl on girl, and some were straight sex.
Inside the store Donna lead us immediately to the arcade area and chose a booth in the center of a an aisle. As soon as we were inside the booth she fed it a bill and the screen began playing. She pushed a button a few times and a tranny movie came on.
At first I wondered why she chose to come here since we had movies like this at home. I heard someone enter the booth next to us and figured it was some guy in there planning on jacking off. Then I noticed a hole in the wall at just about dick level for a man. Donna sat next to the hole and then motioned for me to come closer. She peeked through the hole and then moved her lips closer so the guy next door could see them. Moments later I saw a rock hard dick coming through.
Donna licked the head of the dick before licking and kissing it as far down as possible before taking him into her mouth. Her head began moving up and down, taking more and more of the stranger's cock in. I was only inches away and watched intently as my wife sucked another man's dick until he began filling her with his cum. She pulled away, her mouth full and then kissed me, giving his cream to me so I could taste it before I swallowed.
“See how easy that was? Next one is yours.”
We traded places and I waited, wondering if I could do what my wife had just done. The wait wasn't more than a few minutes. I heard him enter the booth and start his movie. Doing as Donna had, I waved a finger through the hole and then put my lips so he could see them. I pulled back and the next thing I knew there was a dick coming through the hole. Leaning forward I tentatively kissed the tip, then began licking him all around and up and down his length. I did this for two or three minutes until I became used to having my mouth touching a cock.
Then, summoning up my courage, I opened my mouth and took him inside, using my tongue on the areas Donna had pointed out earlier. I felt like a complete slut, sucking on dick belonging to a man I'd never even seen before. This actually was a real turn on and my mouth was soon traveling up and down again and again. I could barely believe I was sucking a cock, much less enjoying it.
“You're doing good, Sharon. Don't forget to swallow when he cums,” Donna whispered in my ear. “Oooo, yea, baby, suck his cock! Keep it up girl, you'll love it when he cums.”
I concentrated on the head of his suck, sucking, twirling my tongue, sucking some more, bobbing my head up and down. I felt him grow stiffer and it almost felt as if he were growing thicker in my mouth. Then it happened. His hot cum began spilling into my mouth and I was proud of my accomplishment. Now I was a cocksucker, of that there could be no doubt.
He stopped cumming and pulled back through the hole so I swished his cum around my mouth, really enjoying the flavor, before swallowing it all.
Donna fed another bill into the slot and I sat and waited for the next one, and then the next and the one after that. All in all, by the time we were ready to leave I had sucked four cocks and swallowed each load of cum I was offered.
“Congratulations, Sharon, you're a bonafide cocksucker,” Donna laughed as we climbed into the car, “and what's more, you loved every second of it! Go on, admit it.”
“Okay, okay,” I laughed, “I'm a cocksucker and I love it! But you didn't seem bashful about sucking that first one.”
“No, I rather enjoyed it and I'm looking forward to the next one,” she admitted freely.
“Me too!”
We'd only been home about fifteen minutes when there was a knock on the door. Donna was in the bathroom so I answered it.
“Sharon? I was looking for Donna. She asked me to drop by and check out a leak.”
“Oh yea, the leak. It's in the kitchen,” I replied and showed him to the leaky faucet.
Sean wasted no time crawling beneath the sink and checking things out.
“Everything looks good down here,” he said.
“The leak is basically when I turn on the water,” Donna said as she entered the room.
“Oh, okay. Then let's have a look up there,” he said and crawled out from under. “Yes, I see it and I know what the problem is. The washer is worn out. Just so happens that I have some at the house. I'll go get one and the tools I'll need,” he said after a few minutes.
“You know, from what he said at the mall I bet he'd do you,” Donna said.
“Give him a blow job?”
“Yea, you could do that but I meant he'd probably fuck you,” she answered with a smile.
“Aw, come on, Donna,” I whined, “you don't really expect me to ...”
“And why not? You expect me to be with another woman as well as another man, and you also would like me to be gang banged. Besides that, you certainly didn't complain when I fucked your girlie ass.”
“But a real dick in my ass?”
“In for a penny, in for a pound,” she said sweetly. “You know you want to get fucked by a man and have an idea of what it feels like to be a woman. Wouldn't you rather that your first time with a man be with someone you knew?”
She was correct, of course, but I didn't want to seem to eager.
“I guess you're right.”
“You know I am. So trot your ass to the bedroom and put on that new teddy. It'll really set off that red hair of yours. And put on those mules with the fluff on them. Oh, take off the stockings and garter belt so he can see your lovely white legs. You can leave your panties on unless he wants you to take them off. And make sure you use plenty of lubricant.”
“Thanks,” I answered with a little fake sarcasm.
“Hurry, before he comes back,” she said and popped my ass with a dish towel.
I took my time changing and stopped to refresh my makeup as well as lube my asshole very well. I heard him return and crept closer so I could listen to what he and Donna were saying.
“You really should let me give you something for this, Sean.”
“I told you it was no bother.”
“But your time is worth something.”
“Don't worry about it. That's what neighbors are for.”
“Then maybe you could teach David a thing or two.”
“Maybe.”
“How do I look, Donna?” I asked as I stepped into the kitchen. Turning around so that she could see I no longer had on my panties as I twirled so the hem of the nightie flew up and away from me.
“You look positively scrumptious, babe,” she replied. “What do you think, Sean?”
He looked at me and I suddenly felt naked.
“Sharon? I'm sorry, I guess you didn't know I was here.”
“Yes, as a matter of fact I did,” I replied and moved a little closer. “I put this on just for you.”
“Obviously you didn't understand me at the mall.”
“I understood perfectly, which is why I put this on.”
“Donna?”
“Sean, you don't recognize David?”
“David?”
“Call me Sharon, please.”
“Um, yes, of course. Well this comes as quite a surprise, David, er, Sharon.”
“Do you like the way I look?”
“Yes, yes of course I do.”
“Than can I give you something for fixing that leak? Anything you want.”
“I think we can work something out,” he smiled.
“Or in,” I giggled.
“Sharon is just discovering her sissy side and is in need of something only a man can supply. Are you interested in helping her?”
“Yes. Yes I am!” Sean replied, never taking his eyes off me.
“Great! Will it bother you if I watch you deflower her?”
“Not if you're okay with it, Sharon.”
“I'm okay. Donna has been so much help in my, uh, transformation.”
“But not in my bed. Use the guest room,” Donna said sharply.
“Come on,” I said and held out my hand.
Sean took my hand and I lead him to the guest bedroom, the same bedroom where so many of our games had taken place, and now I figured out why Donna had decorated it in this manner, so totally girlie. She must have been planning this for at least two years and I'd never even had the slightest clue until now. Here I was now, a cock sucking crossdresser anxious to allow a man take my virgin boy pussy.
I turned and began to unbutton his shirt and he held me for a long, long kiss, nearly taking my breath away. His hands had roamed up and down my back, feeling my ass, cupping the cheeks, kneading them. I was almost instantly turned on by his actions, even though I had never really thought I could be.
“For a woman, Sharon, you're really hot,” he groaned.
“Yea, I'm so hot,” I moaned back. “I need you, Sean. Damn, I need you so badly.” while I was talking my fingers were fumbling with the snap of his jeans. Honestly, I couldn't believe I was doing this, experiencing these feeling, this need for a hard cock in my ass pussy.
Sean stepped out of his pants and pushed me back on the bed, laying between my legs and kissing me deeply.
I'd only caught a glimpse of his cock but saw enough to know he was bigger than me, quite a bit longer and twice as thick. I knew it was going to hurt when he entered me and I didn't care. The need to have him inside me had taken over completely. I didn't understand these feelings only the overwhelming desire to give myself to a man.
“Suck his cock, Sharon. Get him nice and hard and wet before he fucks you,” Donna directed.
That's what I did, using the skill I'd learned this afternoon I took Sean's rapidly growing cock into my mouth and got him very hard. Now I could see just how big he was and I definitely knew it was going to hurt,
Sean stopped me after a few minutes and position me on my hands and knee. The moment had arrived and I was ready to be mounted. I wanted him to mount me, to make me feel like a woman, to spill his see deep in my ass pussy.
Sean moved himself so his cock was barely touching my tiny hole and I felt myself wanting him more than anything else in the world. He pressed against me, the massive head of his dick opening me slightly. I was relaxing as much as I could but it still hurt terrifically to be stretched open by him.
“Oooohhhh,” I moaned, “you're so big!”
He pushed harder and gained a little more ground but he wasn't in me yet. Once again he pressed and I felt myself open up even more. The pain was mind numbing, much more than when Donna had fucked me with her dildo, and yet I pushed back against him, wanting him.
“You're damn tight, Sharon,” he gasped and pushed even harder.
I was on the verge of screaming and telling him to stop when he suddenly slid all the way into me and it felt so good. I was full of man cock and I couldn't help but want more of him.
Sean waited until I was accustomed to his size and then slowly pulled back until only the head remained inside. He held for a second and then pushed back inside. Again and again he pulled back and then pushed inside, each time a little faster than the time before. After several strokes he was really pounding me, his balls slapping against me.
“Oooo, yyyesss! Yyyesss! Oh fuck me, Sean, fuck me!” I squealed as he took me places I'd never been before. This was so much better than Donna's strap on dildo.
Picking up the pace, Sean slammed his thick cock in and out of me until I felt me dick spewing onto the bed. I couldn't believe I was cumming without any stimulation to my dick, or clit as Donna called it.
“I'm cumming! Oh, baby, I'm cumming!” I groaned as I left a puddle of cum on the bedspread.
He grabbed my hips and kept fucking me until I was reduced to a babbling idiot, loving the feel of his dick sliding in and out, wanting so desperately for him to fill me with cum.
“Do it! Do it, Sean! Cum in the sissy's cunt! Show what it feels like for a woman to satisfy her man!” Donna yelled, her fingers flying in and out of her naked pussy.
Several hard thrusts later I felt him stiffen and jerk and then I felt his hot seed boiling into me, spreading its wonderful heat throughout. I was on the verge of another orgasm but I didn't reach it, like a woman after a man is finished. But the feel of his hot cum inside me was more than worth the pain and the almost second orgasm.
He collapsed on top of me and drive me onto the mattress beneath him, his cock throbbing and oozing more and more cum deep in my bowels while we basked in the afterglow of our union. Five minutes later he slid out of me and I felt a flood of his cum flow from my just fucked ass pussy and down over my balls.
Sean rolled me over and kissed me again, his heavy cock laying across my smaller one.
“Thank you,” I sighed when he finished.
“The pleasure was mine,” he grinned.
“Will I see you again?”
“Sure, I'm just across the street and Donna wants me to come over and take care of some things around the house.”
“I mean, will you fuck me again?”
“Yes, if that's what you want.”
“Yes, please,” I answered and smiled up at him.
I knew I had crossed a line today and I could never, would never, go back. I was a crossdressing, cock sucking, take it in the ass, sissy and I loved it.
I climbed out of bed and silently padded to the bathroom to begin my transformation. First came a long, hot bath which included shaving my legs silky smooth and then my armpits followed by my pubic area. Donna had insisted that I keep these areas shaved at all times, which pretty much left me hairless all over. Since we'd had my facial hair removed permanently via electrolysis I no longer had to worry about that area. Next I painstakingly applied my makeup to achieve the look I preferred. Finally I took out the breast forms and applied the adhesive to them and my natural breasts so they wouldn't slip out of place. I loved how they felt and looked, moving with me when I walked or bent over. With this out of the way I slipped on a natural hair wig and brushed it back to style before I sat on the counter and painted my nails, both finger and toe. I normally kept my toe nails painted since they were out of sight when I was at work. Actually I wore panties to work daily and usually stockings as well.
Today would be the first time Donna had ever taken me out in public and I needed everything to be perfect. When I finished and gazed into the mirror all I could see was a pretty red haired woman looking back at me. Well, that is, until my gaze looked at the dick between my legs but that would be taken care of later when I had it tucked away.
Ready for whatever challenges faced me, I slipped into a long, soft, pink robe and went to the kitchen for a morning cup of coffee. Of course, I would have to make it first. It was just about ready when Donna came in.
“Good morning, sexy,” she said as she entered the kitchen and I poured her a steaming cup.
“Good morning, lover,” I smiled and sat at the table with her. I never ceased to be amazed when I looked at my lovely wife.
“Are you ready to make your public debut?”
“As ready as I'll ever be,” I replied, wondering if I was really ready.
“You'll love the freedom of going out as a woman, babe. Besides, you know you want to. Hell, you've always wanted to go out all dressed up.”
“Maybe in my fantasies,” I laughed. “But this is different. I mean, it's broad daylight.”
“That's okay. Believe me, no one will ever know. You've got the walk down pat, and your voice is perfect. Today we're a couple of women going shopping at the mall.”
The mall meant I would really be on public display so I had better be able to pass as a woman without a hitch.
“If you're a good girl I'll have a big surprise for you tonight.”
That usually meant one thing. She'd be fucking me with her strap on dildo again, an act I had immediately loved from the first time we'd had sex like this.
“Oooo, sounds like I better be a good girl,” I laughed and kissed her.
I went back to the bedroom and found that she had already laid out my clothes for the day. I'd be wearing a knee length, loose fitting yellow dress, a white thong, garter belt, nude stockings, and four inch open toe white heels. Nothing to draw any undue attention to me, for which I was thankful. As far as accessories went, Donna had chosen a gold anklet, a pretty heart shaped necklace, a dainty wrist watch, a nice pearl ring to replace my wedding band, dangling earrings, and a charm bracelet for me to wear.
“Well, how do I look?” I asked after I was ready.
Naturally it hadn't taken Donna nearly as long to get ready so she was waiting for me to make my appearance.
“Sexy!” she exclaimed. “I think you'll be drawing more attention than me finally.”
“No way. You're way too pretty and so damn sexy,” I replied, grinning at her.
“Don't be too sure of that. Pretty soon you'll have to fight off the men with a stick.”
“Yea, right. A man in a dress compared to a sexy little vixen like yourself? Don't be silly.”
“Babe, you don't even come close to looking like a man in a dress anymore. You're a hot woman and you really need to act the part.”
“Okay, I guess you want me to flirt a little while I'm at it,” I said, teasingly.
“Wouldn't hurt my feelings if you did. As a matter of fact, you flirt with a man and so will I. After all, we'll be at the mall, so what could happen?”
“Good point,” I laughed and picked up my purse after I made sure I had everything I needed in it.
Donna had drilled me at length on what I should carry in my purse. I had lipstick, a compact, tissues, a tampon, wallet, house and car key, cell phone, credit cards and cash. I was as ready to go as I'd ever be.
Donna drove in case we happened to get pulled over for some reason, which was the most logical course. Beside, I was still too nervous to even think about driving. We arrived at the mall and walked a long way to get to the entrance. I think Donna did this on purpose so I could be seen by more and more people. Much to my relief, most of the people were busy concentrating on their shopping and didn't give me more than a cursory glance.
Inside the mall Donna and I did a lot of window shopping, slowly moving through the mall. She did, however, steer us into a high end lingerie store where we picked out a very sexy emerald green and black teddy with lace insets for me and a lovely purple one for her.
“You'll look very hot in that little number, Sharon,” she told me. “And yes, I want you to wear it tonight. In fact, I want you to change into it as soon as we get home so I can take some pictures of your sexy ass.”
I really enjoyed posing for Donna and it actually helped me become more feminine and sexy even though the only one who'd every actually seen me, until today, was my wife. Of course, this wasn't counting the thousands who saw my pictures on line. There were hundreds of pictures of me in various states of dress and undress, even some with Donna fucking me with her strap on and some where I was fucking her with my own dick before cleaning her pussy, and all the while dressed as Sharon.
From the lingerie store we moved on to a shoe store where Donna picked out a pair of sandals with five inch stiletto heels and straps that traveled up to my calves. I thought they were a bit over the top but she insisted that I get them.
“After all, baby, they'll make you look like such a whore with that short, skin tight dress I bought for you,” Donna laughed in front of the salesman.
“You're right,” I giggled, “they certainly will.”
“Will you help me with these?” I asked the salesman.
“Of course,” he answered and knelt to help me get them on and laced properly. “Lovely feet.”
“Thank you,” I answered and smiled sweetly. I have to admit that his hands on my feet felt wonderful, sending an electrical charge up my spine. For the first time in my life I looked at another man with more than a passing interest. I actually found myself wondering what he might be like in bed.
“You do that so well,” I smiled and wondered if this was flirting according to Donna.
“Lot's of practice,” he replied and smiled up at me.
Then it struck me that he had the most beautiful bright blue eyes that seemed to see into your soul and sparkled when he smiled. I could almost feel myself melting under his gaze.
Once the shoes were secured to me, he helped me stand so I could walk around the store and check out the way they felt. I don't think I meant to do it, and honestly don't know why I did it, but I know I put a little extra wiggle in my walk.
Donna met me at the far end of the store and commented with a giggle, “Keep it up, Sharon, and this guy will want to fuck you in the back room.”
“Keep up what?”
“That sexy walk. You're practically begging him to fuck you,” she replied and laughed aloud.
“What? No I'm not!” I protested with a little too much vigor.
We bought the shoes and I wore them out of the store, liking the way they looked and felt, and really liking the way they made me feel. After some more window shopping we wound up at the food court for a cool drink and a slice of pizza.
I needed to go to the little girl's room so I excused myself for a few minutes. When I came back Donna was talking to a man I recognized as our neighbor. I held back for a minute hoping he would go away but it became obvious he was in no hurry so I sucked it up and returned to our table.
“Oh Sharon, this is our neighbor, Sean. Sean, this is Sharon.”
“Very pleased to meet you,” he smiled and held out his hand.
“My pleasure,” I replied and took his hand. If he recognized me his face and manners certainly didn't show it.
Sean stayed with us and talked to Donna for several minutes about his plans to landscape his backyard. Occasionally I made some comment on what he was doing but never really got into the conversation. In fact, I was looking at our neighbor in a different light, thinking of him more as a potential partner in sex, than anything to do with landscaping.
Why was I even having thoughts like this? Was it because I was dressed like, and acting like, a woman? Sure, lots of men had some sort of masturbation fantasies about being a woman and being taken by a man, but I never had, at least until now. Now I couldn't keep from thinking how it would feel to have his hard cock in my mouth or even up my ass instead of the role playing Donna and I did with her strap on.
“Sure, I'll come over and take a look at it. No promises that I can fix the problem. It's a shame David isn't more of a handy man.”
“No, it's a shame he isn't more of a man,” she replied. “Especially in the bedroom.”
“Oops. That's one problem you'll have to figure out on your own, honey,” Sean said and smiled.
“Why is that?”
“Honestly, and I mean total honesty, you'd be safe sleeping in my bed totally naked. Sorry, but you're not exactly my type.”
“I see and understand perfectly,” Donna answered when she realized he really wasn't into women. “But you will take a look at the leak?”
“Of course I will. Um, will David understand if he comes home and finds me alone with you?”
“You won't be. Sharon will be there with us.”
“Good. I'd hate for there to be some misunderstanding.”
Donna laughed and then replied, “There won't be. Everything is crystal clear.”
“Good. I'll try and get over there this afternoon and take a look.”
“Thank you. I've been after David for months to do something but I'm afraid he'd make it worse and plumbers are so expensive.”
“I know. That's one of the reasons I learned how to fix things myself,” he laughed and got up to leave.
Once he was out of hearing range I said to Donna, “What's the idea of telling him something as intimate as the bedroom? Were you trying to get laid?”
“The thought crossed my mind. Besides you flirted with the man at the shoe store. I'm just showing you how a woman goes about flirting.”
“Yea, yea. You know, if I did something like that either you'd get mad or the guy might expect me to follow through,” I said and then grinned.
“And what would Sharon do if a man wanted her?” Donna asked a little too innocently.
“Probably run away screaming,” I laughed, hoping to avoid the subject.
“I think otherwise, I think Sharon would get on her knees and suck his cock like a good little girl.”
“Huh? Why do you say that?”
“That's what I would do,” she laughed. “Besides, I think it would be so hot to see you do something like that, or maybe something more. You know how much you enjoy it when I fuck you're ass pussy. Just imagine what it would be like with a real dick that pumped you full of hot cream.”
“Do you really want to see me with a man?” I asked, already knowing the answer. Donna and I and talked about this very thing on several occasions and I knew just how hot it made her.
“I think it would be so hot,” she replied quickly. “And besides, how many times have you said you wanted to see me with another woman or very well hung man? Or for that matter, you've even suggested a gang bang.”
“Okay, okay, I get the picture,” I sighed. It was true, I'd expressed my fantasies of seeing her with other men and women, so I suppose turn about was fair play. Donna obviously wanted me to have sex with a man, but could I actually do it? Could I suck a dick? I wasn't sure if I could or not. Did I want to suck a dick? I had to admit that the idea was quite intriguing.
“I will if you will,” she said and smiled mischievously.
“Okay, you're on,” I answered suddenly.
“I knew you'd say that. Are you ready to take this crossdressing thing to the next level? Are you ready to find out what it really feels like to be a woman?”
Looking her in the eyes I answered, “I'm willing to give it a try.”
“I have a feeling you'll love it,” she laughed.
“Hell, I don't even have a clue how to find a man who'll fuck another man in a dress.”
“Don't worry, I think I know someone who'd do you in a heartbeat.”
“Okay then, I'll leave it up to you to find me a guy to have sex with,” I laughed, “and a woman for yourself. I know a man who would give up his left nut to take you to bed.”
“And you'll be there watching while wearing a dress.”
That was a new wrinkle but even though that would mean letting a friend know I was a crossdresser I was okay with it.
“Okay.”
“And when he finishes you'll eat my pussy and his cum.”
“Okay.”
“And when another woman and I have sex you'll be in a dress.”
“Yes,” I agreed. For some reason I couldn't fathom, the thought of sucking a cock, or even taking a hard cock up my ass, was somehow appealing.
“Well, okay then. I guess the first thing you need to do is learn how to suck a dick and I know just how to teach you,” Donna laughed. “You see, I've been doing quite a bit of research on this subject because I knew you were going to agree.”
“You did? How?”
“You were way too easy to get dressed in women's clothes and never once objected to the makeup, or going out in public. You were way too quick learning how to walk and talk and do your makeup. In my opinion, this is something you've always wanted to do, whether you knew it or not.”
I didn't answer her because I was thinking back to some of my masturbation fantasies when I was growing up. More often than not I imagined that some guy was either fucking me or I was sucking his cock and getting a mouthful of cum.
“Ready?” Donna asked.
“Yes, I guess I am.”
We left the mall and I noticed I had more spring in my step than usual and Donna was in a much happier mood than I'd seen her in for a while. Was this because I was going to learn how to suck a cock or because she was going to have sex with other men?
Soon enough we were in the car and she was driving away with a destination in mind.
“You have to remember to lick and kiss a man's dick from one end to the other but pay special attention to the head. They really love it when you tongue the rim around the head,” she was saying as she drove. “Oh, if he cums in your mouth be sure to swallow. They really like that. You can taste his seed of course, and I recommend that. Hell, you'll love tasting other guy's cum. We already know you like your own. But then there's always the one that wants to cum on your face, so be prepared for that also. Some men also like being verbal, calling you all sorts of names like slut, whore, cocksucker, and in your case, fagot, queer or sissy. Don't be offended, it's just a way that they get more stimulated.”
“Okay, I can understand the name calling.”
“Are you ready for your lessons to begin?”
Suddenly I began looking forward to learning how to suck a man's dick. “Yes. Yes, I believe I am.”
“Good,” she answered and pulled into an adult book store we'd been to on several occasions where we had purchased her strap on as well as quite a few movies, some of which had been those with transvestites, a few were girl on girl, and some were straight sex.
Inside the store Donna lead us immediately to the arcade area and chose a booth in the center of a an aisle. As soon as we were inside the booth she fed it a bill and the screen began playing. She pushed a button a few times and a tranny movie came on.
At first I wondered why she chose to come here since we had movies like this at home. I heard someone enter the booth next to us and figured it was some guy in there planning on jacking off. Then I noticed a hole in the wall at just about dick level for a man. Donna sat next to the hole and then motioned for me to come closer. She peeked through the hole and then moved her lips closer so the guy next door could see them. Moments later I saw a rock hard dick coming through.
Donna licked the head of the dick before licking and kissing it as far down as possible before taking him into her mouth. Her head began moving up and down, taking more and more of the stranger's cock in. I was only inches away and watched intently as my wife sucked another man's dick until he began filling her with his cum. She pulled away, her mouth full and then kissed me, giving his cream to me so I could taste it before I swallowed.
“See how easy that was? Next one is yours.”
We traded places and I waited, wondering if I could do what my wife had just done. The wait wasn't more than a few minutes. I heard him enter the booth and start his movie. Doing as Donna had, I waved a finger through the hole and then put my lips so he could see them. I pulled back and the next thing I knew there was a dick coming through the hole. Leaning forward I tentatively kissed the tip, then began licking him all around and up and down his length. I did this for two or three minutes until I became used to having my mouth touching a cock.
Then, summoning up my courage, I opened my mouth and took him inside, using my tongue on the areas Donna had pointed out earlier. I felt like a complete slut, sucking on dick belonging to a man I'd never even seen before. This actually was a real turn on and my mouth was soon traveling up and down again and again. I could barely believe I was sucking a cock, much less enjoying it.
“You're doing good, Sharon. Don't forget to swallow when he cums,” Donna whispered in my ear. “Oooo, yea, baby, suck his cock! Keep it up girl, you'll love it when he cums.”
I concentrated on the head of his suck, sucking, twirling my tongue, sucking some more, bobbing my head up and down. I felt him grow stiffer and it almost felt as if he were growing thicker in my mouth. Then it happened. His hot cum began spilling into my mouth and I was proud of my accomplishment. Now I was a cocksucker, of that there could be no doubt.
He stopped cumming and pulled back through the hole so I swished his cum around my mouth, really enjoying the flavor, before swallowing it all.
Donna fed another bill into the slot and I sat and waited for the next one, and then the next and the one after that. All in all, by the time we were ready to leave I had sucked four cocks and swallowed each load of cum I was offered.
“Congratulations, Sharon, you're a bonafide cocksucker,” Donna laughed as we climbed into the car, “and what's more, you loved every second of it! Go on, admit it.”
“Okay, okay,” I laughed, “I'm a cocksucker and I love it! But you didn't seem bashful about sucking that first one.”
“No, I rather enjoyed it and I'm looking forward to the next one,” she admitted freely.
“Me too!”
We'd only been home about fifteen minutes when there was a knock on the door. Donna was in the bathroom so I answered it.
“Sharon? I was looking for Donna. She asked me to drop by and check out a leak.”
“Oh yea, the leak. It's in the kitchen,” I replied and showed him to the leaky faucet.
Sean wasted no time crawling beneath the sink and checking things out.
“Everything looks good down here,” he said.
“The leak is basically when I turn on the water,” Donna said as she entered the room.
“Oh, okay. Then let's have a look up there,” he said and crawled out from under. “Yes, I see it and I know what the problem is. The washer is worn out. Just so happens that I have some at the house. I'll go get one and the tools I'll need,” he said after a few minutes.
“You know, from what he said at the mall I bet he'd do you,” Donna said.
“Give him a blow job?”
“Yea, you could do that but I meant he'd probably fuck you,” she answered with a smile.
“Aw, come on, Donna,” I whined, “you don't really expect me to ...”
“And why not? You expect me to be with another woman as well as another man, and you also would like me to be gang banged. Besides that, you certainly didn't complain when I fucked your girlie ass.”
“But a real dick in my ass?”
“In for a penny, in for a pound,” she said sweetly. “You know you want to get fucked by a man and have an idea of what it feels like to be a woman. Wouldn't you rather that your first time with a man be with someone you knew?”
She was correct, of course, but I didn't want to seem to eager.
“I guess you're right.”
“You know I am. So trot your ass to the bedroom and put on that new teddy. It'll really set off that red hair of yours. And put on those mules with the fluff on them. Oh, take off the stockings and garter belt so he can see your lovely white legs. You can leave your panties on unless he wants you to take them off. And make sure you use plenty of lubricant.”
“Thanks,” I answered with a little fake sarcasm.
“Hurry, before he comes back,” she said and popped my ass with a dish towel.
I took my time changing and stopped to refresh my makeup as well as lube my asshole very well. I heard him return and crept closer so I could listen to what he and Donna were saying.
“You really should let me give you something for this, Sean.”
“I told you it was no bother.”
“But your time is worth something.”
“Don't worry about it. That's what neighbors are for.”
“Then maybe you could teach David a thing or two.”
“Maybe.”
“How do I look, Donna?” I asked as I stepped into the kitchen. Turning around so that she could see I no longer had on my panties as I twirled so the hem of the nightie flew up and away from me.
“You look positively scrumptious, babe,” she replied. “What do you think, Sean?”
He looked at me and I suddenly felt naked.
“Sharon? I'm sorry, I guess you didn't know I was here.”
“Yes, as a matter of fact I did,” I replied and moved a little closer. “I put this on just for you.”
“Obviously you didn't understand me at the mall.”
“I understood perfectly, which is why I put this on.”
“Donna?”
“Sean, you don't recognize David?”
“David?”
“Call me Sharon, please.”
“Um, yes, of course. Well this comes as quite a surprise, David, er, Sharon.”
“Do you like the way I look?”
“Yes, yes of course I do.”
“Than can I give you something for fixing that leak? Anything you want.”
“I think we can work something out,” he smiled.
“Or in,” I giggled.
“Sharon is just discovering her sissy side and is in need of something only a man can supply. Are you interested in helping her?”
“Yes. Yes I am!” Sean replied, never taking his eyes off me.
“Great! Will it bother you if I watch you deflower her?”
“Not if you're okay with it, Sharon.”
“I'm okay. Donna has been so much help in my, uh, transformation.”
“But not in my bed. Use the guest room,” Donna said sharply.
“Come on,” I said and held out my hand.
Sean took my hand and I lead him to the guest bedroom, the same bedroom where so many of our games had taken place, and now I figured out why Donna had decorated it in this manner, so totally girlie. She must have been planning this for at least two years and I'd never even had the slightest clue until now. Here I was now, a cock sucking crossdresser anxious to allow a man take my virgin boy pussy.
I turned and began to unbutton his shirt and he held me for a long, long kiss, nearly taking my breath away. His hands had roamed up and down my back, feeling my ass, cupping the cheeks, kneading them. I was almost instantly turned on by his actions, even though I had never really thought I could be.
“For a woman, Sharon, you're really hot,” he groaned.
“Yea, I'm so hot,” I moaned back. “I need you, Sean. Damn, I need you so badly.” while I was talking my fingers were fumbling with the snap of his jeans. Honestly, I couldn't believe I was doing this, experiencing these feeling, this need for a hard cock in my ass pussy.
Sean stepped out of his pants and pushed me back on the bed, laying between my legs and kissing me deeply.
I'd only caught a glimpse of his cock but saw enough to know he was bigger than me, quite a bit longer and twice as thick. I knew it was going to hurt when he entered me and I didn't care. The need to have him inside me had taken over completely. I didn't understand these feelings only the overwhelming desire to give myself to a man.
“Suck his cock, Sharon. Get him nice and hard and wet before he fucks you,” Donna directed.
That's what I did, using the skill I'd learned this afternoon I took Sean's rapidly growing cock into my mouth and got him very hard. Now I could see just how big he was and I definitely knew it was going to hurt,
Sean stopped me after a few minutes and position me on my hands and knee. The moment had arrived and I was ready to be mounted. I wanted him to mount me, to make me feel like a woman, to spill his see deep in my ass pussy.
Sean moved himself so his cock was barely touching my tiny hole and I felt myself wanting him more than anything else in the world. He pressed against me, the massive head of his dick opening me slightly. I was relaxing as much as I could but it still hurt terrifically to be stretched open by him.
“Oooohhhh,” I moaned, “you're so big!”
He pushed harder and gained a little more ground but he wasn't in me yet. Once again he pressed and I felt myself open up even more. The pain was mind numbing, much more than when Donna had fucked me with her dildo, and yet I pushed back against him, wanting him.
“You're damn tight, Sharon,” he gasped and pushed even harder.
I was on the verge of screaming and telling him to stop when he suddenly slid all the way into me and it felt so good. I was full of man cock and I couldn't help but want more of him.
Sean waited until I was accustomed to his size and then slowly pulled back until only the head remained inside. He held for a second and then pushed back inside. Again and again he pulled back and then pushed inside, each time a little faster than the time before. After several strokes he was really pounding me, his balls slapping against me.
“Oooo, yyyesss! Yyyesss! Oh fuck me, Sean, fuck me!” I squealed as he took me places I'd never been before. This was so much better than Donna's strap on dildo.
Picking up the pace, Sean slammed his thick cock in and out of me until I felt me dick spewing onto the bed. I couldn't believe I was cumming without any stimulation to my dick, or clit as Donna called it.
“I'm cumming! Oh, baby, I'm cumming!” I groaned as I left a puddle of cum on the bedspread.
He grabbed my hips and kept fucking me until I was reduced to a babbling idiot, loving the feel of his dick sliding in and out, wanting so desperately for him to fill me with cum.
“Do it! Do it, Sean! Cum in the sissy's cunt! Show what it feels like for a woman to satisfy her man!” Donna yelled, her fingers flying in and out of her naked pussy.
Several hard thrusts later I felt him stiffen and jerk and then I felt his hot seed boiling into me, spreading its wonderful heat throughout. I was on the verge of another orgasm but I didn't reach it, like a woman after a man is finished. But the feel of his hot cum inside me was more than worth the pain and the almost second orgasm.
He collapsed on top of me and drive me onto the mattress beneath him, his cock throbbing and oozing more and more cum deep in my bowels while we basked in the afterglow of our union. Five minutes later he slid out of me and I felt a flood of his cum flow from my just fucked ass pussy and down over my balls.
Sean rolled me over and kissed me again, his heavy cock laying across my smaller one.
“Thank you,” I sighed when he finished.
“The pleasure was mine,” he grinned.
“Will I see you again?”
“Sure, I'm just across the street and Donna wants me to come over and take care of some things around the house.”
“I mean, will you fuck me again?”
“Yes, if that's what you want.”
“Yes, please,” I answered and smiled up at him.
I knew I had crossed a line today and I could never, would never, go back. I was a crossdressing, cock sucking, take it in the ass, sissy and I loved it.
Becky
- 10.10.2021
- 33
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- Category:
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