Mom Goes Camping With Son Son s Friend
- 4 years ago
- 109
- 0
Steve & Stephane free porn video
For as long as Steve could remember he never knew where this fetish came from. There was a part of him that thinks it was growing up in a house full of women. Being the only male made it rough but at least he had his own room when he got older. His three older sisters had to share because they were at least the same sex.
Living with Stephanie made it all the harder for him to do this, but he found his ways. Thankfully sometimes they would work off schedules so she would be at work and he would have the apartment to himself. Today was one of those days. He was off and she was going to work. He got to sleep in and as she kissed him good-bye he was already planning his entire day.
When the door went click he jumped out of the bed and began his ritual. He waited a full 30 minutes to make sure that she was gone and had not “forgotten” something. She almost caught him that one time. It was after that experience that he told himself he was going to tell her, but he always chickened out. He just did not have the heart to try to explain it all to her, hell he did not even know why he did it himself. He just did it and he liked it.
Once he was sure the coast was clear he made himself a cup of coffee and went back to their bedroom. Made the bed and began the search. He found what he was looking for and laid it all out on the bed. He sat down and pondered them for a second and could feel his dick getting hard just thinking about it. But it was too soon for him to indulge himself, he had other shit to do to complete this process.
He filled up his coffee and let his cock settle down. Stepping outside in his PJ’s he soaked up the early morning sun as he sipped his coffee. These were the days that he enjoyed the best. He got to have it all to himself and no one would be the wiser.
After he was done with his coffee he jumped in the shower and made sure the water was hot, but not too hot. With the water running over his body he again tried to think what was it in his past that made this happen, but as he tried to get his mind to find it, the image would slip out of his head.
Once he was clean he pulled on his robe and went to the room again to sit on the bed and contemplate the best way to go about this. Sure, he was an over thinker, but it required that. He had to have it all right or it just would not work. He decided to rummage again and came up with something better.
It was now time to fulfill his need.
Pulling on Stephanie’s panties felt so good. The silk rubbing against his hair as he pulled them up made his dick get hard instantly. Trying to position it in the shear fabric was always a chore, but with so much practice he was a pro. All that stuck out was the head of his cock after he secured it with the elastic band of the panties. There was already a drop of pre cum glistening so he took a tissue and cleaned it off.
He was standing there looking at himself in the mirror feeling so dirty and ashamed that he had not told his girlfriend about all of this. But it felt so good and there were just times that he had to do it. He was so engrossed in his ritual that he did not hear the door open or close.
What he did hear was “WHAT THE FUCK IS GOING ON”. He snapped his head around and there she was jaw almost to the floor…
He thought about lying to her, but he couldn't think that fast of a convincing story. Besides, once she looked at what was laid out on the bed, he knew making up any tale would be pointless.
Atop the bed was her full length satin nightgown, but what was even more embarrassing was his bra he painstakingly kept hidden from her. Through the beauty of mail order, he had been able to obtain a bra made for women who had double mastectomies. It gave the look as well as the feel of having breasts.
Finally pulling her eyes off him, she looked at the items on the bed. Walking over and picking up the bra and examining it she said, " I guess this wasn't a spur of the moment curiosity thing. How long has this been going on?"
He knew he had lost her so he saw no sense in not owning up. He admitted having the fetsish since his teenage years. He didn't know why but did add that every time he put on panties, a brief image of his older sisters entering his bedroom came to mind, but as quickly as the image formed, it dissolved just as quickly, as if his brain slammed the door before he could enter the chamber that held those memories.
"Why Didn’t you tell me?" She said.
"I knew you wouldn't understand and I didn't want to lose you."
She stepped closer and as she stared at the image of the head of his erection protruding from the elastic of the panties she wore only yesterday, he couldn't tell if her reaction was of revulsion, disgust or pity.
He went to remove the panties but she stopped him. Picking up the bra she told him to put it on. Not knowing what to do, he shrugged into it and hooked it on.
Picking up her nightgown she placed it over his head and pulled it down over him.
She stepped back and examined him. He braced himself for whatever came next. Ridicule? A tirade?
One thing he wasn’t prepared for was her smile. Then with a chuckle she said, " you make a really ugly woman. Let's see what we can do about that"
Steven was shocked, he did not know how lucky he was. “You’re OK with this?”
“Well, I guess I’m going to have to indulge you on this and I’m OK with that. What I am not OK with is you stretching out my panties.” Stephanie replied and adding “If you’re going to dress like a woman, you’re going to need to do more than just wear my panties, dresses and bras. There is a lot more to what we have to do than just clothes. Now, jump in the shower, we’ve got a lot of work to do.”
He hurriedly pulled off the nightgown, bra and panties and rushed into the bathroom. He was so happy and excited that she was going to play along with this.
When she heard the water turn on it gave her a moment to reflect on this. Everything happened so fast, she felt as though she just got caught up in this. Although she had never seen his face glow with joy when her anger turned soft. She could even feel herself getting wet thinking about this, but she had worked out one part of her plan.
She got a towel, scissors, one of her disposable razors and the shaving cream and got it all ready on the bed. That left her enough time to pick up “his” clothes and put them away.
Steven came back from the shower wrapped in a towel. His dick was still poking out it was clear that he did not jerk off in the shower to take care of that. Seeing it she had another idea in her plan. It seemed that everything was coming in bits and pieces.
“Ok, take off the towel and let me see you.” She half commanded half joking asked.
He took off the towel and the first thing that her mind said was “We’ve got a lot of work here”. She looked him over like a painter looks at a blank canvas. “Sit lay down sweetie, we’ve got a lot of work to do.” She said as she gestured with the scissors toward the towel on the bed.
She could see the apprehension on his face. “Don’t worry I’m not going to cut off your beautiful dick… just get over here”.
He walked over and sat down on the towel and just looked at here not knowing what to say and then placed his back against the bed looking up at the ceiling. Waiting for her to do what she had in mind.
“One of the first things that women learn is that men (for some reason) don’t like hair, we’ve got a lot of hair to remove down here.” She said gently grabbing his still hard dick.
“Wait, what” he asked.
“You like to dress like a woman right, well you need to do this.”
“Um…”
She did not wait for a response and began trimming down his pubic hair to a more manageable length. Once she got enough removed she took out the shaving cream and smothered his cock and balls with it. He clearly liked this part because she could feel his dick pulsing as she rubbed it in.
She took care as she shaved to remove all of his hair. Each time she would get near his cock or balls he would tense up. Not from worry of her cutting him, but from the sensation of having her touch him. She felt bad not just jerking him off, but women feel sexual frustration all the time, and this was a side lesson.
A strange feeling was creeping over her as she was taking off all of his pubic hair. With each stroke of the razor something was being awaked inside of her. She did not know what it was, but she was feeling more confidant in this, and was actually enjoying it.
Once she was done with his pubic hair she looked at it, and it did make his dick look bigger. There was still a lot of hair. “Scoot up” she commanded, and surprisingly there was no push back from him this time. He did as she said and moved up.
This was going to be easier as she lathered up his legs and started taking all of that hair off as well. As with his pubic hair with each stroke of the razor she could feel him giving way and accepting what she was doing. He was now in her hands and she was loving it. Once she was done she got up and said.
“Ok, let’s see what you look like now.”
He got off the bed and stood again in front of the mirror naked. He felt so powerless in her hands but this was feeding his need better than just wearing her clothes.
“What do you think?” She asked.
“I never knew how smooth I would feel.”
“You like it?”
“Yes”
“Good, you’ll need to keep it off everyday, that is what we have to do. Now, put on these” she said as she tossed him a fresh pair of black panties “you can stretch those out, but we need to get you your own pair.”
As he pulled them on the feeling was wonderful. As the silk ran up his now clean legs it was more electric than before. When the fabric hit his balls he almost cam right there. He positioned his dick as he always did by folding it up and securing it with the elastic.
“This feels so good” he said turning toward her hoping that she would help with his need to cum he was so turned on that was all that he could think about was either jerking off or fucking her good.
“I’m glad you like it, but really you cannot keep stretching out mine. Get your pants and shirt on we’re going shopping.”
“I, I, I, can’t go out with this” he said looking down at his cock still sticking out.
“Oh sweetie, just cause you’re horny does not mean you get to have a release, that is part of being a woman.” She cooed as she walked over to him and whispered in his ear “Just be glad I’m not making you go out in my gown.”
Their first stop was Victorias secret. Stephen had browsed in there many times but never had the nerve to buy anything. She immediately went over to the thong section.
“Being that you keep suggesting I wear thongs despite my telling you they're not my style, I assume you just wanted to be able to borrow them every once in a while.”
While he did admit that that was one of the reasons, he also assured her that he thought shed look good in them.
She picked out a couple of pairs in his size, along with other styles that she knew he'd enjoy feeling against him.
Next they moved to the negligee section. While she was looking through the rack at floor length ones she noticed him fingering a babydoll style.
" those are pretty 70s, she said, but buy them if they suit you.
His hard on was throbbing as he felt the different fabrics.
Their next stop was the department store where she bought him stockings and pantyhose.
In the shoe department, whenever no one was looking she had him try on different high heeled shoes.
In the wig department, telling the clerk they had a costume party coming up, she had him try on different wigs. When he saw the price he tried to tell her a wig wasn't necessary since he wouldn't be leaving the house when he was dressed as a woman but she smiled and said, "You never know."
When they got home she laid out all that they bought on the bed and took a seat. “You’re going to need to get dressed up sweetie. I want to watch you.”
He took off his pants and shirt then his/her panties. “You can keep those since you stretched them out” she said as he tried to hand them back to her. He pulled on a pair of red thongs and adjusted his dick accordingly. She loved how gingerly he did all of this. Next, he pulled the garters on and then rolled on the stockings on over his smooth legs and snapped the garters on. Next came his special bra that gave him some “tits”. She could see his cock getting harder and harder as each piece came on.
He stood there admiring himself in the mirror for a second and turned to her. “How do I look” he asked hoping for some reassurance from her. “You’re missing something” you’re missing something she said as she tossed the wig to him.
“But…”
“But what, you wanted to do this, now be a good girl and put it on for me”.
He did not want to put up a fight so he pulled the wig on, and turned toward the mirror. The red hair of the wig fell down around his “tits” and framed his face pretty well. As he admired himself in the mirror she walked over to him and came into the mirror resting her chin on his shoulder admiring him.
“Some ground rules now” she said as she reached around and adjusted his cocks position. She could feel that he was about to cum. Then rattled off the commandments she was thinking of for all of this.
1. When you’re dressed up you are no longer Stephen but Susan.
2. Susan does what I want, no talk back, no sass, and when I want
3. Susan is always a good girl and never plays with her self unless told to
4. You can only wear my clothes when I give you permission
“Now, I’ve got to get something else for you, but go ahead and get one of my skirts out, and when I get back we will talk about this further.”
With that she squeezed his dick hard causing him to wince and she was gone.
Susan, did not want to disappoint this time and found a black mini skirt and pulled it on over her new clothes. It did a better job of hiding his hard cock than just the thongs. She then found a blouse that would fit and pulled it over the wig and adjusted it to show some of her “tits”. Finally she put on the heels and looked in the mirror again. She could not imagine that this was actually happening. He rubbed his dick through the skirt, but remembered rule #3 and stopped.
He took the time while she was gone to try to learn to walk in heels. He did not know how they did it. He would lose his balance, but then regain it again. After a few trips up and down the hallway he was gaining the confidence of learning how to do this.
He was walking around the apartment in no time. Then, the door opened and there she was holding a plain brown bag. “Good girl, you’re getting the hang of it. We’re still not done. Go in the bathroom, and I’ll be shortly”. As she headed toward the bedroom Susan went to the bathroom.
Stephanie came in shortly and gave him a kiss on the cheek. “One last thing Susan, you’re going to need to learn how to do makeup”.
As she applied the makeup Susan would catch glimpses of the transformation happening. When she was done Stephen/Susan was amazed at the transformation.
“Now, lets go get a drink” Stephanie said.
“What! NO!”
She slapped his ass hard. “What did you say”.
“I’m not going outside like this”.
Again another swat to his ass. Even though it was covered he could feel the flesh hurt.
“What is rule #2?”
“I’m a good girl, and do as I’m told”
“Good, now we are getting a drink, or are we going to have to do this the hard way?”
With that she left the bathroom and headed toward the door…
As they walked out the door he prayed that none of his neighbors were outside. He was sure they wouldn't recognize him from a distance but what if they approached them to chat. Luckily the block was empty and he quickly got in the car.
"You'll have to let me order the drinks" she said, " your voice will be a dead giveaway."
They went into the club. Luckily it wasn't too crowded since he still felt worried that he could pull this off.
They grabbed 2 seats at the bar. As he sat on the stool he sat with his legs open. Stephanie slapped his leg and told him to close his legs, that it wasn't ladylike.
She ordered two girlie drinks and as he nursed his he noticed 2 guys at the end of the bar giving them the eye, though most of their attention was on Stephanie.
Uh oh, he thought as one sauntered over.
"My friend and I would like to buy you gals a drink"
When Stephanie politely turned him down he said, " but 2 ladies shouldn't have to be alone"
With that she gave him a smile but then reached out and placed her arm around Stephen.
"But we're not alone" she said, and kissed Stephen sexily.
"I should have figured" the guy said and walked back to his friend. He said something to him and they both laughed.
After a few drinks they headed home as soon as they got in the door Stephanie guided him into the bedroom. She undid his skirt and let it fall to the floor before pushing him onto the bed.
Slipping his dick out of his panties but leaving his balls covered, she massaged his sack over the sheer fabric.
"I have to say, she said, " I don't think your dick has ever been harder. I'm going to enjoy the new you"
With that she reached under her skirt and slipped her panties off. Straddling him she immediately slipped him inside her.
"Oh yeah, she said, " I'm definitely going to enjoy the new you"
As his cleanly shaven dick slid into her he almost came. There was too much going on. But he kept it back and grabbed her hips. And thrust her down on to him. The sensation of their cleanly shaven crotches rubbing together felt great. She was right, his dick was the hardest it had ever been. As Stephanie kept grinding him his hips met her at all the right times.
“FUCK SUSAN, FUCK ME” Stephanie moaned as she bounced on his dick trying to get as much of it as possible. He could feel her body tense up as she was about to cum, but he had not be given the go ahead yet, and was trying his best to not cum. As her pussy quivered on his dick and her warm juice flowed onto his panties she slid a finger into his ass and said “you can cum now”.
He never felt an orgasm so powerful course though his body. She was still fucking him as his cum shot deep into her. She collapsed onto him and let out a sigh. She rolled off of him and put her fingers into her pussy and swabbed up some of his cum as it dripped out of her and held it up to his mouth. “You’ll need to taste yourself for me”. He eagerly sucked her finger in and was surprised of the taste. It was a mix of him and her, and was magical.
They again had conflicting work schedules that week and hardly saw each other. Keeping to her orders that he couldn't masturbate he found himself with a permanent erection and it hurt. At night before going to sleep he would conjure up lurid fantasies in hopes that he would have a wet dream, thereby relieving himself and still sticking to the rules.
But what he missed most was the feel of women’s underwear on his body. Bending the rules, yet not technically breaking them, he took a pair of his silkiest panties and slipped them under his underwear so that he could feel them against his erection. Although it felt great, it actually only made his anxiety worse.
Not being able to take it anymore he called Stephanie at work and begged her to give him permission to jerk off.
"I'll tell you what" she said, hold on till my dinner break and I'll come home during it"
He paced the floor until her arrival. When she got home she told him to remove his pants and underwear. While he was doing that she took 2 dining room chairs and placed them across from each other in the middle of the living room. Having him sit in one she began taking off her skirt. As she began slipping out of her panties he almost came without touching himself but held back.
She sat in the other chair and spread her legs wide.
"Okay" she said, "start masturbating on the count of three and if you can hold out until I cum, you can play dress up all night"
She counted to 3 and they both began getting themselves off. She teased him by starting slow, just running her fingering over her clit. He tried to slow down his own playing but the sight of her bare pussy was too much and he quickly picked up the pace.
Even when she began rubbing herself faster, even slipping her fingers inside her to moisten them, he doubted he could hold on long enough to win.
He had one trick up his sleeve he knew he had to try. Knowing how much she liked dirty talk in bed he began talking to her, telling her how much he wanted to fuck that pussy of hers, how he wanted to cum on her face, how he wanted to bend her over and fuck her up the ass.
She shut her eyes and moaned and began to rub herself harder so he kept up the dirty talk, describing how he would cum on her tits and then lick his own cum off her.
"FUCK!!!!!" She cried out and began to orgasm. When he knew she wasn't faking to trick him into cumming first, he held out his free hand and shot his load into it. The relief it brought him made him dizzy.
"You win" she said, getting up to get dressed. "Have fun tonight"
He was in the room before she could even pick her panties up off the floor. Digging out the pair he wanted to wear. It was one of the thongs she got him. Even though he just came as he pulled them on he could feel his dick getting hard. It did feel a little weird as the fabric slid between his ass cheeks but once he got it positioned and wiggled his ass it began to feel just fine.
His erection was back and he positioned it perfectly. As he assembled his clothing she walked into the bedroom. Seeing her man in the red thongs and the fabric up his ass crack made pussy leak. She did enjoy the sex from these experiences and when he became Susan, he fucked her in ways that she only dreamed about. That alone was worth it. Watching him dress made her just think of how hot he words made her feel and how she lost the bet.
She walked over to him and kissed his cheek as he pulled up the skirt making sure to hide is cock. “You make such a good girl, we’re going out tonight”. Half hoping that he would put up a fight, but she was just as pleased when he said “Sure”. Clearly he was more interested in getting dressed so she also decided to get ready for some nice drinks with Susan.
In no time they were in the car and off to a cocktail bar. As she pulled the car into a parking spot she put out the scenario for the night “Tonight, I’m going to walk in first. Once I have a seat I’ll text you. I want to see them check you out. I’m still ordering drinks, but I just want to see their heads turn.”
She turned off the car and got out. Walking into the bar she found a table at the furthest end of the bar in a dark corner and texted him. She waited for him to walk in and kept scanning the place. When Stephen/Susan walked in she could see some heads turn. It made her pussy wet seeing men and even some women look as he/she walked through the bar. Stephanie purposely did not tell him/her where she was sitting to make sure the time spent looking, and therefore more eyes on him/her, was as long as possible.
As each head turned her pussy tingled. Thankfully the bar was dark enough that when her hand slipped under her own skirt to touch her wet pussy no one could see. Finally Stephen/Susan found her and sat down. Stephanie lightly brushed her finger dripping with pussy juice across his mouth as she kissed him. “This is what you’re doing to me” she said as they settled in for a night of good drinks. Even with the girl-on-girl kiss, or because of, there were more eyes on them. Too bad that the “pussy” they wanted to fuck when they looked as Stephen/Susan was actually an asshole. She was sure that some guys would more than likely kick his ass than fuck it though.
After a few drinks Steph’s pussy was burning with desire and she needed her woman/mans dick inside of her. “We, need to go now” she said as she grabbed her purse. And headed toward the door. She sped home just thinking how hard his dick must be. She did not think that she could drive fast enough, each red light seemed to last an hour and every stop sign seemed to be backed up.
Finally, they got home and before they could close and lock the front door she hiked up his skirt and pulled his panties aside freeing his dick. She turned around and pulled up her own skirt and pulled down her own panties. She bent over in front of him giving him a view of what she wanted.
He did not need any more direction than that. Her pussy was so wet that as he slid in her juices already started dripping out as his dick filled her up. When he slid all the way in and the silk hit her ass she let out a groan. “FUCK ME” She moaned as he pumped in and out of her. She was wild with desire as his dick was pounding her pussy. Each time his dick slid in more pussy juice came out.
In, Out, In, Out, In, Out, In Out, he kept up his savage attack on her pussy. When his fingers hit her clit that pushed her over the edge and her orgasm came on her hard and fast. She was panting so hard trying to catch her breath that she did could not get enough oxygen. As the second wave hit her body and his dick hit deep inside of her she blacked out.
When she came to a few second later he was down on the floor with her dick still hard.
“Are you ok?” he asked with clear concern on his face.
“Oh, yeah, I just hyperventilated for a second.” But her needs were still not met. “Lets go into the bedroom” she said as she got up on her wobble knees and headed toward the bedroom.
He followed right behind her. Leave your clothes on she whispered as she pulled off her skirt and top. He was on her as she laid down on the bed. She grabbed his dick still slick with her juice and guided it toward her ass. As his head gently slid in she let out a gasp. He slowly worked his dick in waiting for her ass hole to accept his dick.
After her muscles accepted it he began slowly sliding in and out. He matched his strokes with his fingers on her clit. After a while he picked up his pace and was soon fucking her ass as he had her pussy. Stephanie was in bliss feeling her ass filled the same way her pussy was previously. She soon felt another orgasm build as he kept pumping her asshole.
She could hold on no longer and soon was having her third orgasm. Her body was shaking again as it hit her in waves. She made sure to breath more calmly this time. She moaned as he pulled his dick out of her ass, she did not like the feeling of not in there, but her need was soon replaced with her 4th orgasm as his hot cum hit her tits. It felt like he was shooting gallons of cum on her.
He collapsed next to her panting with exhaustion. As she stoked the sweaty hair from his eyes he lifted his head and began to lick her tits clean (as he promised in their bet). They both feel asleep in bliss as her pussy was still soaking wet from the fucking she just received.
The next day Stephen had to go to work, but she got to stay home. As he was getting ready she was sitting in bed watching him get ready. “You were so good last night, I wanted to ask you how far you’re willing to go?”
“What do you mean?”
“Here let me show you” she said as she got out of the bed and went to the closet. She pulled out the paper sack she bought so many days ago and pulled out a small butt plug and a strap on.
His eyes got wide when he saw them. “Just give it a try, if you’re going to dress like a girl. It will take some time, but that’s why you’re wearing it to work today, you might like it more if you put on your panties”
She watched as he tried to insert the butt plug with no success. Finally she had him bend over and she slipped a finger inside him to relax the muscles. She then applied some of her lubricant to it and was able to slide it in. As he stood up she asked how it felt.
"Like I'm constipated. I have new respect for you gals that let us put out dicks up there"
She laughed and watched him put his underwear on, not yet ready to take a chance wearing panties to work.
"When did you first find out you liked wearing women’s clothes?" She asked.
"As far back as I can remember. When I was still in grammar school, we had this neighbor, she was a bit overweight but she always hung her underwear out on the line with the rest of her laundry. I snuck over one day and stole a pair. Even though they were way too big for me I still enjoyed wearing them"
"Why didn't you just steal your sisters?"
"I did but they all wore white cotton ones and they didn’t feel good, and I thought it would be too weird to wear my moms."
He got dressed and went to work. When he left, she took a shower, relishing how finding out his fetish has put new excitement into their relationship. She wondered just how far she could get him to try new things.
She thought back to how she always loved how he took his time undressing her in bed. She found it so erotic but now she wondered if the reason for his slowness was more to check the feel of her clothes than for pleasuring her.
At work Stephen still felt uncomfortable with the plug. He couldn't imagine being able to handle the strap on. He practiced relaxing his muscles and after awhile even succeeded in relaxing them so much that the plug fell out. This gave him hope. Although he wasn't too keen about getting fucked back there he had seen the gleam in Stephanie’s eyes as she showed it to him so he knew shed enjoy it. He decided that if she was willing to put up with his fetish, then he would obviously do whatever turned her on. He wondered if she herself had any secret fetish she hadn't told him about.
Living with Stephanie made it all the harder for him to do this, but he found his ways. Thankfully sometimes they would work off schedules so she would be at work and he would have the apartment to himself. Today was one of those days. He was off and she was going to work. He got to sleep in and as she kissed him good-bye he was already planning his entire day.
When the door went click he jumped out of the bed and began his ritual. He waited a full 30 minutes to make sure that she was gone and had not “forgotten” something. She almost caught him that one time. It was after that experience that he told himself he was going to tell her, but he always chickened out. He just did not have the heart to try to explain it all to her, hell he did not even know why he did it himself. He just did it and he liked it.
Once he was sure the coast was clear he made himself a cup of coffee and went back to their bedroom. Made the bed and began the search. He found what he was looking for and laid it all out on the bed. He sat down and pondered them for a second and could feel his dick getting hard just thinking about it. But it was too soon for him to indulge himself, he had other shit to do to complete this process.
He filled up his coffee and let his cock settle down. Stepping outside in his PJ’s he soaked up the early morning sun as he sipped his coffee. These were the days that he enjoyed the best. He got to have it all to himself and no one would be the wiser.
After he was done with his coffee he jumped in the shower and made sure the water was hot, but not too hot. With the water running over his body he again tried to think what was it in his past that made this happen, but as he tried to get his mind to find it, the image would slip out of his head.
Once he was clean he pulled on his robe and went to the room again to sit on the bed and contemplate the best way to go about this. Sure, he was an over thinker, but it required that. He had to have it all right or it just would not work. He decided to rummage again and came up with something better.
It was now time to fulfill his need.
Pulling on Stephanie’s panties felt so good. The silk rubbing against his hair as he pulled them up made his dick get hard instantly. Trying to position it in the shear fabric was always a chore, but with so much practice he was a pro. All that stuck out was the head of his cock after he secured it with the elastic band of the panties. There was already a drop of pre cum glistening so he took a tissue and cleaned it off.
He was standing there looking at himself in the mirror feeling so dirty and ashamed that he had not told his girlfriend about all of this. But it felt so good and there were just times that he had to do it. He was so engrossed in his ritual that he did not hear the door open or close.
What he did hear was “WHAT THE FUCK IS GOING ON”. He snapped his head around and there she was jaw almost to the floor…
He thought about lying to her, but he couldn't think that fast of a convincing story. Besides, once she looked at what was laid out on the bed, he knew making up any tale would be pointless.
Atop the bed was her full length satin nightgown, but what was even more embarrassing was his bra he painstakingly kept hidden from her. Through the beauty of mail order, he had been able to obtain a bra made for women who had double mastectomies. It gave the look as well as the feel of having breasts.
Finally pulling her eyes off him, she looked at the items on the bed. Walking over and picking up the bra and examining it she said, " I guess this wasn't a spur of the moment curiosity thing. How long has this been going on?"
He knew he had lost her so he saw no sense in not owning up. He admitted having the fetsish since his teenage years. He didn't know why but did add that every time he put on panties, a brief image of his older sisters entering his bedroom came to mind, but as quickly as the image formed, it dissolved just as quickly, as if his brain slammed the door before he could enter the chamber that held those memories.
"Why Didn’t you tell me?" She said.
"I knew you wouldn't understand and I didn't want to lose you."
She stepped closer and as she stared at the image of the head of his erection protruding from the elastic of the panties she wore only yesterday, he couldn't tell if her reaction was of revulsion, disgust or pity.
He went to remove the panties but she stopped him. Picking up the bra she told him to put it on. Not knowing what to do, he shrugged into it and hooked it on.
Picking up her nightgown she placed it over his head and pulled it down over him.
She stepped back and examined him. He braced himself for whatever came next. Ridicule? A tirade?
One thing he wasn’t prepared for was her smile. Then with a chuckle she said, " you make a really ugly woman. Let's see what we can do about that"
Steven was shocked, he did not know how lucky he was. “You’re OK with this?”
“Well, I guess I’m going to have to indulge you on this and I’m OK with that. What I am not OK with is you stretching out my panties.” Stephanie replied and adding “If you’re going to dress like a woman, you’re going to need to do more than just wear my panties, dresses and bras. There is a lot more to what we have to do than just clothes. Now, jump in the shower, we’ve got a lot of work to do.”
He hurriedly pulled off the nightgown, bra and panties and rushed into the bathroom. He was so happy and excited that she was going to play along with this.
When she heard the water turn on it gave her a moment to reflect on this. Everything happened so fast, she felt as though she just got caught up in this. Although she had never seen his face glow with joy when her anger turned soft. She could even feel herself getting wet thinking about this, but she had worked out one part of her plan.
She got a towel, scissors, one of her disposable razors and the shaving cream and got it all ready on the bed. That left her enough time to pick up “his” clothes and put them away.
Steven came back from the shower wrapped in a towel. His dick was still poking out it was clear that he did not jerk off in the shower to take care of that. Seeing it she had another idea in her plan. It seemed that everything was coming in bits and pieces.
“Ok, take off the towel and let me see you.” She half commanded half joking asked.
He took off the towel and the first thing that her mind said was “We’ve got a lot of work here”. She looked him over like a painter looks at a blank canvas. “Sit lay down sweetie, we’ve got a lot of work to do.” She said as she gestured with the scissors toward the towel on the bed.
She could see the apprehension on his face. “Don’t worry I’m not going to cut off your beautiful dick… just get over here”.
He walked over and sat down on the towel and just looked at here not knowing what to say and then placed his back against the bed looking up at the ceiling. Waiting for her to do what she had in mind.
“One of the first things that women learn is that men (for some reason) don’t like hair, we’ve got a lot of hair to remove down here.” She said gently grabbing his still hard dick.
“Wait, what” he asked.
“You like to dress like a woman right, well you need to do this.”
“Um…”
She did not wait for a response and began trimming down his pubic hair to a more manageable length. Once she got enough removed she took out the shaving cream and smothered his cock and balls with it. He clearly liked this part because she could feel his dick pulsing as she rubbed it in.
She took care as she shaved to remove all of his hair. Each time she would get near his cock or balls he would tense up. Not from worry of her cutting him, but from the sensation of having her touch him. She felt bad not just jerking him off, but women feel sexual frustration all the time, and this was a side lesson.
A strange feeling was creeping over her as she was taking off all of his pubic hair. With each stroke of the razor something was being awaked inside of her. She did not know what it was, but she was feeling more confidant in this, and was actually enjoying it.
Once she was done with his pubic hair she looked at it, and it did make his dick look bigger. There was still a lot of hair. “Scoot up” she commanded, and surprisingly there was no push back from him this time. He did as she said and moved up.
This was going to be easier as she lathered up his legs and started taking all of that hair off as well. As with his pubic hair with each stroke of the razor she could feel him giving way and accepting what she was doing. He was now in her hands and she was loving it. Once she was done she got up and said.
“Ok, let’s see what you look like now.”
He got off the bed and stood again in front of the mirror naked. He felt so powerless in her hands but this was feeding his need better than just wearing her clothes.
“What do you think?” She asked.
“I never knew how smooth I would feel.”
“You like it?”
“Yes”
“Good, you’ll need to keep it off everyday, that is what we have to do. Now, put on these” she said as she tossed him a fresh pair of black panties “you can stretch those out, but we need to get you your own pair.”
As he pulled them on the feeling was wonderful. As the silk ran up his now clean legs it was more electric than before. When the fabric hit his balls he almost cam right there. He positioned his dick as he always did by folding it up and securing it with the elastic.
“This feels so good” he said turning toward her hoping that she would help with his need to cum he was so turned on that was all that he could think about was either jerking off or fucking her good.
“I’m glad you like it, but really you cannot keep stretching out mine. Get your pants and shirt on we’re going shopping.”
“I, I, I, can’t go out with this” he said looking down at his cock still sticking out.
“Oh sweetie, just cause you’re horny does not mean you get to have a release, that is part of being a woman.” She cooed as she walked over to him and whispered in his ear “Just be glad I’m not making you go out in my gown.”
Their first stop was Victorias secret. Stephen had browsed in there many times but never had the nerve to buy anything. She immediately went over to the thong section.
“Being that you keep suggesting I wear thongs despite my telling you they're not my style, I assume you just wanted to be able to borrow them every once in a while.”
While he did admit that that was one of the reasons, he also assured her that he thought shed look good in them.
She picked out a couple of pairs in his size, along with other styles that she knew he'd enjoy feeling against him.
Next they moved to the negligee section. While she was looking through the rack at floor length ones she noticed him fingering a babydoll style.
" those are pretty 70s, she said, but buy them if they suit you.
His hard on was throbbing as he felt the different fabrics.
Their next stop was the department store where she bought him stockings and pantyhose.
In the shoe department, whenever no one was looking she had him try on different high heeled shoes.
In the wig department, telling the clerk they had a costume party coming up, she had him try on different wigs. When he saw the price he tried to tell her a wig wasn't necessary since he wouldn't be leaving the house when he was dressed as a woman but she smiled and said, "You never know."
When they got home she laid out all that they bought on the bed and took a seat. “You’re going to need to get dressed up sweetie. I want to watch you.”
He took off his pants and shirt then his/her panties. “You can keep those since you stretched them out” she said as he tried to hand them back to her. He pulled on a pair of red thongs and adjusted his dick accordingly. She loved how gingerly he did all of this. Next, he pulled the garters on and then rolled on the stockings on over his smooth legs and snapped the garters on. Next came his special bra that gave him some “tits”. She could see his cock getting harder and harder as each piece came on.
He stood there admiring himself in the mirror for a second and turned to her. “How do I look” he asked hoping for some reassurance from her. “You’re missing something” you’re missing something she said as she tossed the wig to him.
“But…”
“But what, you wanted to do this, now be a good girl and put it on for me”.
He did not want to put up a fight so he pulled the wig on, and turned toward the mirror. The red hair of the wig fell down around his “tits” and framed his face pretty well. As he admired himself in the mirror she walked over to him and came into the mirror resting her chin on his shoulder admiring him.
“Some ground rules now” she said as she reached around and adjusted his cocks position. She could feel that he was about to cum. Then rattled off the commandments she was thinking of for all of this.
1. When you’re dressed up you are no longer Stephen but Susan.
2. Susan does what I want, no talk back, no sass, and when I want
3. Susan is always a good girl and never plays with her self unless told to
4. You can only wear my clothes when I give you permission
“Now, I’ve got to get something else for you, but go ahead and get one of my skirts out, and when I get back we will talk about this further.”
With that she squeezed his dick hard causing him to wince and she was gone.
Susan, did not want to disappoint this time and found a black mini skirt and pulled it on over her new clothes. It did a better job of hiding his hard cock than just the thongs. She then found a blouse that would fit and pulled it over the wig and adjusted it to show some of her “tits”. Finally she put on the heels and looked in the mirror again. She could not imagine that this was actually happening. He rubbed his dick through the skirt, but remembered rule #3 and stopped.
He took the time while she was gone to try to learn to walk in heels. He did not know how they did it. He would lose his balance, but then regain it again. After a few trips up and down the hallway he was gaining the confidence of learning how to do this.
He was walking around the apartment in no time. Then, the door opened and there she was holding a plain brown bag. “Good girl, you’re getting the hang of it. We’re still not done. Go in the bathroom, and I’ll be shortly”. As she headed toward the bedroom Susan went to the bathroom.
Stephanie came in shortly and gave him a kiss on the cheek. “One last thing Susan, you’re going to need to learn how to do makeup”.
As she applied the makeup Susan would catch glimpses of the transformation happening. When she was done Stephen/Susan was amazed at the transformation.
“Now, lets go get a drink” Stephanie said.
“What! NO!”
She slapped his ass hard. “What did you say”.
“I’m not going outside like this”.
Again another swat to his ass. Even though it was covered he could feel the flesh hurt.
“What is rule #2?”
“I’m a good girl, and do as I’m told”
“Good, now we are getting a drink, or are we going to have to do this the hard way?”
With that she left the bathroom and headed toward the door…
As they walked out the door he prayed that none of his neighbors were outside. He was sure they wouldn't recognize him from a distance but what if they approached them to chat. Luckily the block was empty and he quickly got in the car.
"You'll have to let me order the drinks" she said, " your voice will be a dead giveaway."
They went into the club. Luckily it wasn't too crowded since he still felt worried that he could pull this off.
They grabbed 2 seats at the bar. As he sat on the stool he sat with his legs open. Stephanie slapped his leg and told him to close his legs, that it wasn't ladylike.
She ordered two girlie drinks and as he nursed his he noticed 2 guys at the end of the bar giving them the eye, though most of their attention was on Stephanie.
Uh oh, he thought as one sauntered over.
"My friend and I would like to buy you gals a drink"
When Stephanie politely turned him down he said, " but 2 ladies shouldn't have to be alone"
With that she gave him a smile but then reached out and placed her arm around Stephen.
"But we're not alone" she said, and kissed Stephen sexily.
"I should have figured" the guy said and walked back to his friend. He said something to him and they both laughed.
After a few drinks they headed home as soon as they got in the door Stephanie guided him into the bedroom. She undid his skirt and let it fall to the floor before pushing him onto the bed.
Slipping his dick out of his panties but leaving his balls covered, she massaged his sack over the sheer fabric.
"I have to say, she said, " I don't think your dick has ever been harder. I'm going to enjoy the new you"
With that she reached under her skirt and slipped her panties off. Straddling him she immediately slipped him inside her.
"Oh yeah, she said, " I'm definitely going to enjoy the new you"
As his cleanly shaven dick slid into her he almost came. There was too much going on. But he kept it back and grabbed her hips. And thrust her down on to him. The sensation of their cleanly shaven crotches rubbing together felt great. She was right, his dick was the hardest it had ever been. As Stephanie kept grinding him his hips met her at all the right times.
“FUCK SUSAN, FUCK ME” Stephanie moaned as she bounced on his dick trying to get as much of it as possible. He could feel her body tense up as she was about to cum, but he had not be given the go ahead yet, and was trying his best to not cum. As her pussy quivered on his dick and her warm juice flowed onto his panties she slid a finger into his ass and said “you can cum now”.
He never felt an orgasm so powerful course though his body. She was still fucking him as his cum shot deep into her. She collapsed onto him and let out a sigh. She rolled off of him and put her fingers into her pussy and swabbed up some of his cum as it dripped out of her and held it up to his mouth. “You’ll need to taste yourself for me”. He eagerly sucked her finger in and was surprised of the taste. It was a mix of him and her, and was magical.
They again had conflicting work schedules that week and hardly saw each other. Keeping to her orders that he couldn't masturbate he found himself with a permanent erection and it hurt. At night before going to sleep he would conjure up lurid fantasies in hopes that he would have a wet dream, thereby relieving himself and still sticking to the rules.
But what he missed most was the feel of women’s underwear on his body. Bending the rules, yet not technically breaking them, he took a pair of his silkiest panties and slipped them under his underwear so that he could feel them against his erection. Although it felt great, it actually only made his anxiety worse.
Not being able to take it anymore he called Stephanie at work and begged her to give him permission to jerk off.
"I'll tell you what" she said, hold on till my dinner break and I'll come home during it"
He paced the floor until her arrival. When she got home she told him to remove his pants and underwear. While he was doing that she took 2 dining room chairs and placed them across from each other in the middle of the living room. Having him sit in one she began taking off her skirt. As she began slipping out of her panties he almost came without touching himself but held back.
She sat in the other chair and spread her legs wide.
"Okay" she said, "start masturbating on the count of three and if you can hold out until I cum, you can play dress up all night"
She counted to 3 and they both began getting themselves off. She teased him by starting slow, just running her fingering over her clit. He tried to slow down his own playing but the sight of her bare pussy was too much and he quickly picked up the pace.
Even when she began rubbing herself faster, even slipping her fingers inside her to moisten them, he doubted he could hold on long enough to win.
He had one trick up his sleeve he knew he had to try. Knowing how much she liked dirty talk in bed he began talking to her, telling her how much he wanted to fuck that pussy of hers, how he wanted to cum on her face, how he wanted to bend her over and fuck her up the ass.
She shut her eyes and moaned and began to rub herself harder so he kept up the dirty talk, describing how he would cum on her tits and then lick his own cum off her.
"FUCK!!!!!" She cried out and began to orgasm. When he knew she wasn't faking to trick him into cumming first, he held out his free hand and shot his load into it. The relief it brought him made him dizzy.
"You win" she said, getting up to get dressed. "Have fun tonight"
He was in the room before she could even pick her panties up off the floor. Digging out the pair he wanted to wear. It was one of the thongs she got him. Even though he just came as he pulled them on he could feel his dick getting hard. It did feel a little weird as the fabric slid between his ass cheeks but once he got it positioned and wiggled his ass it began to feel just fine.
His erection was back and he positioned it perfectly. As he assembled his clothing she walked into the bedroom. Seeing her man in the red thongs and the fabric up his ass crack made pussy leak. She did enjoy the sex from these experiences and when he became Susan, he fucked her in ways that she only dreamed about. That alone was worth it. Watching him dress made her just think of how hot he words made her feel and how she lost the bet.
She walked over to him and kissed his cheek as he pulled up the skirt making sure to hide is cock. “You make such a good girl, we’re going out tonight”. Half hoping that he would put up a fight, but she was just as pleased when he said “Sure”. Clearly he was more interested in getting dressed so she also decided to get ready for some nice drinks with Susan.
In no time they were in the car and off to a cocktail bar. As she pulled the car into a parking spot she put out the scenario for the night “Tonight, I’m going to walk in first. Once I have a seat I’ll text you. I want to see them check you out. I’m still ordering drinks, but I just want to see their heads turn.”
She turned off the car and got out. Walking into the bar she found a table at the furthest end of the bar in a dark corner and texted him. She waited for him to walk in and kept scanning the place. When Stephen/Susan walked in she could see some heads turn. It made her pussy wet seeing men and even some women look as he/she walked through the bar. Stephanie purposely did not tell him/her where she was sitting to make sure the time spent looking, and therefore more eyes on him/her, was as long as possible.
As each head turned her pussy tingled. Thankfully the bar was dark enough that when her hand slipped under her own skirt to touch her wet pussy no one could see. Finally Stephen/Susan found her and sat down. Stephanie lightly brushed her finger dripping with pussy juice across his mouth as she kissed him. “This is what you’re doing to me” she said as they settled in for a night of good drinks. Even with the girl-on-girl kiss, or because of, there were more eyes on them. Too bad that the “pussy” they wanted to fuck when they looked as Stephen/Susan was actually an asshole. She was sure that some guys would more than likely kick his ass than fuck it though.
After a few drinks Steph’s pussy was burning with desire and she needed her woman/mans dick inside of her. “We, need to go now” she said as she grabbed her purse. And headed toward the door. She sped home just thinking how hard his dick must be. She did not think that she could drive fast enough, each red light seemed to last an hour and every stop sign seemed to be backed up.
Finally, they got home and before they could close and lock the front door she hiked up his skirt and pulled his panties aside freeing his dick. She turned around and pulled up her own skirt and pulled down her own panties. She bent over in front of him giving him a view of what she wanted.
He did not need any more direction than that. Her pussy was so wet that as he slid in her juices already started dripping out as his dick filled her up. When he slid all the way in and the silk hit her ass she let out a groan. “FUCK ME” She moaned as he pumped in and out of her. She was wild with desire as his dick was pounding her pussy. Each time his dick slid in more pussy juice came out.
In, Out, In, Out, In, Out, In Out, he kept up his savage attack on her pussy. When his fingers hit her clit that pushed her over the edge and her orgasm came on her hard and fast. She was panting so hard trying to catch her breath that she did could not get enough oxygen. As the second wave hit her body and his dick hit deep inside of her she blacked out.
When she came to a few second later he was down on the floor with her dick still hard.
“Are you ok?” he asked with clear concern on his face.
“Oh, yeah, I just hyperventilated for a second.” But her needs were still not met. “Lets go into the bedroom” she said as she got up on her wobble knees and headed toward the bedroom.
He followed right behind her. Leave your clothes on she whispered as she pulled off her skirt and top. He was on her as she laid down on the bed. She grabbed his dick still slick with her juice and guided it toward her ass. As his head gently slid in she let out a gasp. He slowly worked his dick in waiting for her ass hole to accept his dick.
After her muscles accepted it he began slowly sliding in and out. He matched his strokes with his fingers on her clit. After a while he picked up his pace and was soon fucking her ass as he had her pussy. Stephanie was in bliss feeling her ass filled the same way her pussy was previously. She soon felt another orgasm build as he kept pumping her asshole.
She could hold on no longer and soon was having her third orgasm. Her body was shaking again as it hit her in waves. She made sure to breath more calmly this time. She moaned as he pulled his dick out of her ass, she did not like the feeling of not in there, but her need was soon replaced with her 4th orgasm as his hot cum hit her tits. It felt like he was shooting gallons of cum on her.
He collapsed next to her panting with exhaustion. As she stoked the sweaty hair from his eyes he lifted his head and began to lick her tits clean (as he promised in their bet). They both feel asleep in bliss as her pussy was still soaking wet from the fucking she just received.
The next day Stephen had to go to work, but she got to stay home. As he was getting ready she was sitting in bed watching him get ready. “You were so good last night, I wanted to ask you how far you’re willing to go?”
“What do you mean?”
“Here let me show you” she said as she got out of the bed and went to the closet. She pulled out the paper sack she bought so many days ago and pulled out a small butt plug and a strap on.
His eyes got wide when he saw them. “Just give it a try, if you’re going to dress like a girl. It will take some time, but that’s why you’re wearing it to work today, you might like it more if you put on your panties”
She watched as he tried to insert the butt plug with no success. Finally she had him bend over and she slipped a finger inside him to relax the muscles. She then applied some of her lubricant to it and was able to slide it in. As he stood up she asked how it felt.
"Like I'm constipated. I have new respect for you gals that let us put out dicks up there"
She laughed and watched him put his underwear on, not yet ready to take a chance wearing panties to work.
"When did you first find out you liked wearing women’s clothes?" She asked.
"As far back as I can remember. When I was still in grammar school, we had this neighbor, she was a bit overweight but she always hung her underwear out on the line with the rest of her laundry. I snuck over one day and stole a pair. Even though they were way too big for me I still enjoyed wearing them"
"Why didn't you just steal your sisters?"
"I did but they all wore white cotton ones and they didn’t feel good, and I thought it would be too weird to wear my moms."
He got dressed and went to work. When he left, she took a shower, relishing how finding out his fetish has put new excitement into their relationship. She wondered just how far she could get him to try new things.
She thought back to how she always loved how he took his time undressing her in bed. She found it so erotic but now she wondered if the reason for his slowness was more to check the feel of her clothes than for pleasuring her.
At work Stephen still felt uncomfortable with the plug. He couldn't imagine being able to handle the strap on. He practiced relaxing his muscles and after awhile even succeeded in relaxing them so much that the plug fell out. This gave him hope. Although he wasn't too keen about getting fucked back there he had seen the gleam in Stephanie’s eyes as she showed it to him so he knew shed enjoy it. He decided that if she was willing to put up with his fetish, then he would obviously do whatever turned her on. He wondered if she herself had any secret fetish she hadn't told him about.
Aeryn
- 27.06.2020
- 21
- 0
