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The weekend started off the same as any other for Dhiren. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturized his legs, stepped into a pair of lacy pink panties and hooked on a matching bra.

The feel of the light, soft, feminine fabric had always been a thrill to Dhiren, ever since that fateful day when, aged fourteen, he found himself alone in the house all day. He put on ladies clothes for the first time — his older sister’s panties and slip — and had felt so aroused he had masturbated almost continuously until he went to bed.

He then inserted into his bra a pair of expensive breast forms that gave him that reassuring weight on his chest and made him feel so much more feminine. Next on was a pair of sheer black hold-up stockings. The nylon felt wonderful against his freshly shaven legs.

Walking into his bedroom, he opened his wardrobe, which was filled with an array of skirts, dresses and tops, but very few masculine clothes. They were all bought by mail order, since he didn’t have the nerve to go shopping for ladies’ clothes. He unhooked a pretty blue and green dress from off its hanger. Pulling it over his head and smoothing it down, he felt immeasurably better and began to put the tensions of the day behind him. He strapped on a pair of black shoes and sat at his dressing table to put on his make-up.

He was always very meticulous with his cosmetics, taking his time so as to do a good job. First he put moisturizer on his face, then foundation cream, blending it into the neckline. He then put blusher on his cheeks and several layers of cherry-red lipstick on his fleshy lips. Afterwards, he carefully applied black eye-liner and penciled in his finely plucked eyebrows. He then brushed on blue eye shadow, applying a lighter shade on the area below the eyebrows and a darker one to his eyelids.

After about fifteen minutes he looked in the mirror and decided it was good enough. He then clipped on a pair of large hoop earrings through his pierced ears, and then put on two rings, a bracelet and a nice gold necklace. He sprayed his neck liberally with his favorite aftershave and finished by painting his nails with a bright pink varnish. He was done. His transformation was complete. He was no longer Dhiren, but Dhiksha, as he liked to think. As ever when he was dressed up, Dhiren felt a tremendous rush of sexual energy and his thoughts immediately turned to men.

But Dhiren’s clothes, make-up and jewelry were cloaking a secret sadness. He knew it even though he tried to deny it to himself. It was a sadness he was increasingly trying to drown in alcohol, which was becoming a worry to him. He desperately needed a boyfriend, but he was too shy, too frightened of people, to go out and find one. He looked back with horror to his early teens, when he had to endure a great deal of nasty name calling and bullying at school because of his delicate, feminine ways.

That had made him turn in on himself and become very isolated. To Dhiren’s credit, however, he had fought back through sheer hard work and his sharp intelligence. He became one of the best students at his school and had gone on to College, where he studied computer science and gained a first with a distinction. He had then obtained a good job as a software engineer with a large plastics company, where he earned enough money to satisfy his craving for all things pertaining to the opposite sex. He moved into a flat in Delhi where he had studied, where he could indulge his passion in perfect anonymity.

Not only did Dhiren spend large sums of money in acquiring a wardrobe and range of cosmetics any shopaholic, fashion conscious girl would have been proud of, but he had even started using hormone creams on his chest, bottom and thighs. The results were disappointing for the first three months or so, then one day he noticed a puffy swelling around his nipples in the bathroom mirror, signaling the beginning of breasts.

His thighs and bottom also began to fill out, his skin becoming softer. He had no idea where all this was going, but he felt compelled to follow the path of increasing femininity. Dhiren wanted desperately to look, dress, think, walk and even sound like a girl. He had developed a passable female voice by following a feminization cd he had found on the internet.Still, he felt a horror of being discovered as a cross-dresser and feared being taken advantage of by more cynical people, being so timid. So he comforted himself with his fantasies.

Indeed, Dhiren’s masturbatory fantasies were extremely lurid. He would insert an anal vibrator inside himself, imagine being taken vigorously from behind, and ejaculate copiously. This evening, as usual, Dhiren reached for his bottle of gin, logged on to his favorite porn site, and watched a succession of gorgeous lady boys being pleasured by handsome men, wishing with all his heart he could be like them. For him, they were the ideal to aspire to; they were so slim, sexy and had lovely small breasts.

Yet Dhiren wasn’t as far behind them as he thought. He was only 5 feet 6, of a very slender build, and had a nice shock of black hair that almost reached his shoulders. He had tried experimenting with wigs but decided his own natural hair looked best. That night he staggered drunkenly into bed and had the worst nightmare of his life. It was a recurring nightmare but this time it felt particularly menacing. He was walking on a path through a dark forest, dressed only in his lingerie and high heels. Every now and then he would come across gay couples having sex.

When they saw him they laughed scornfully at his inability to be his true self. It carried on like this until he left the forest, a storm of derisory laughter sending him on his way. He walked on until he came to another forest, where the same humiliation was repeated, then another forest, again and again.

Dhiren woke up in a cold sweat, terrified and very upset. He put his head in his hands and cried for several minutes, which made him feel a little better. Then he felt a determination that he had not experienced since school, when he resolved that the bullies would not drive him to suicide. He must break out of his isolation and meet a man, someone who would really care for him. Anything would be better than this gradual descent into alcohol dependency and depression.

So Dhiren decided to place an advert in the personals column of a very respectable newspaper. The ad went something like this: Intelligent 21 year old, lover of animals and literature would like to meet older man 25-30 for friendship, perhaps more. Dhiren sent the ad off, already feeling better that he was doing something positive to improve his situation.

The ad appeared in the paper over a couple of weekends. The first week, nothing happened, but on the Monday of the second week, Dhiren received three calls, all from guys who wanted to meet him. Dhiren arranged to meet them all over the course of the week for a drink. Dhiren honoured the dates but nothing came of them. He was so shy he couldn’t give the best of himself and didn’t know how to start or maintain a conversation. Anyway, he wasn’t impressed with his dates. They all seemed to want someone more outgoing and fun-loving, whereas Dhiren was very reserved.

Dhiren was beginning to feel it had all been a waste of time. He received no more calls for two weeks. Then, out of the blue, on a Saturday, he received a call from a man, obviously Delhite, who wanted to see him. Could Dhiren meet him that very night? Why not, thought Dhiren. They arranged to meet outside a pub called ‘Ghungroos’. Dhiren made the ten minute walk and waited nervously, his newspaper tucked under his arm; the old tried and tested method of being identified on blind dates. Dhiren felt a mixture of apprehension and anticipation. He had been in very few pubs full stop, let alone gay bars.

The arranged meeting time of 8 o’clock passed. At ten minutes past, Dhiren thought sadly there was no point in waiting any longer when a tall, nice-looking man approached Dhiren and asked in a polite voice if he was the guy had had rung earlier.

Dhiren immediately recognized him to be a lecturer from the College, from the History department to be precise. “Hi, I’m Demongay,” he said, holding out his hand.

“I’m Dhiren.” They shook hands warmly, and then Demongay motioned Dhiren inside the pub.

“Don’t I know you from somewhere?” asked Demongay.

“You might have seen me at the College where you teach. I left there just a few months ago.”

Demongay’s eyes reflected pleasure that Dhiren knew who he was. At least they had something in common. Demongay asked Dhiren what he studied and what he was doing now. Dhiren felt at ease with him, and spoke openly without nervousness. They moved on to talk about relationships, Dhiren not being ashamed to admit he hadn’t really had any. It turned out that Demongay had just broken up with his ex-girlfriend rather acrimoniously and wanted to find someone else.

The wine flowed and the evening flew by. They talked more freely with one another. Dhiren had never spoken so openly about his thoughts and feelings and found Demongay to be utterly refreshing as a person as well as easy on the eye. However, Dhiren didn’t mention his cross-dressing. At a certain point in the evening, Demongay decided to take a chance and stroked Dhiren’s wrist under the table. The effect on Dhiren was dramatic. It was as if sparks were shooting up his arm. He didn’t pull his hand away, much to Demongay’s relief. Indeed, he squeezed Demongay’s hand tightly and smiled at him, as if to assure him his touch was very welcome.

Eleven o’clock arrived and Demongay announced he had to go home. “Do you live very far away, Dhiren?”

“It’s just a ten minute walk.”

“I’ll walk with you then, if I may.”

“Of course you can!” Dhiren felt so comfortable with this man. He particularly liked the way he called him “honey” and “baby” in that charming American way.

They started off together towards Dhiren’s flat, continuing their conversation. When they drew close to Dhiren’s flat, Demongay persuaded him to make a little detour behind a wall which hid them from the main street. “Listen, Dhiren. I’ve had a great evening. You’re really sweet and I’d like to see you again.”

“I’ve really enjoyed it too, Demongay. Of course I’ll see you again.”

Demongay held Dhiren around the waist and asked if he could kiss him. Dhiren nodded and put his arms around Demongay’s neck. There followed the most delicious moment of Dhiren’s sad young life as Demongay’s mouth met his in a very short but oh so sweet kiss. Dhiren’s heart was thumping. He couldn’t believe this turnaround in his fortunes. They walked the remaining distance to Dhiren’s flat together. Demongay promised to ring the next day.

Only the call didn’t come. Dhiren’s heart sank. Just when he felt his life was on the up, his hopes had been dashed once again. The next day was the same. Dhiren reflected sadly that Demongay was just too good for the likes of him. It was Friday when his phone rang. Dhiren replied in a tone filled with hopelessness. It was Demongay.

“Listen, Dhiren. I’m so sorry. I had to go away for a few days in a hurry and stupidly I forgot to take your number. If you’ll forgive me I’d like to take you out this evening. That is, if you’re not doing anything else.”

Dhiren knew from his tone that his apologies were genuine. His heart leapt at hearing Demongay’s voice again, and his spirits were given an immense boost. “No I’m not doing anything else, Demongay. Just give me half an hour to get ready!”

“OK. I’ll call for you!”

Dhiren hastily pulled on his jeans, t-shirt and a thick black sweater as the early spring weather was still quite cold. His doorbell rang. Opening the door, Dhiren could see that Demongay’s face was full of regret. “Hi babe,” said Demongay kissing Dhiren tenderly on the cheek. “I feel really guilty about not ringing you the other day. Let me make it up to you. We’ll go for a drink then a meal. It’s all on me.”

“Sounds good to me,” replied Dhiren. “You had me really worried, I must admit. But I’m sure you had good reasons for having to go away. Please let’s not mention it anymore.”

They spent a delicious evening together, drinking several glasses of wine in one of the smarter bars in town, and then heading off to a pizza restaurant. Demongay was very frank with Dhiren about the series of disastrous relationships he had had. His personal life was almost at the opposite extreme to his professional life, which was very successful. At the age of 29, he was already regarded nationally as an expert in his field. Dhiren suddenly felt that, in return, he had to be honest with Demongay.

“Listen, Demongay I have something to tell you,” Dhiren said in a nervous voice. “I’ve been really worried about this and I hope you don’t think me strange or anything, but…at home I dress as a lady. I’ve been doing it for years.”

“Well, so what?” said Demongay, astonished that he’d even raised the issue. He grasped Dhiren’s hand to reassure him. “After all, it’s a free country! How far do you go with your dressing up?”

“The works: clothes, make-up, accessories, jewelry, the lot. I’ve even managed to develop a girl’s voice.”

“That’s cool.” Demongay felt himself grow hard in his shorts. He had always been secretly turned on by the thought of boys wanting to appear more like girls.

As for Dhiren, it was as if a huge weight had been lifted from his shoulders. They proceeded to talk freely about Dhiren’s fashion preferences and how he began cross-dressing. Dhiren felt enormously liberated. He had never talked like this so frankly with anyone.

“Listen, Dhiren. Why can’t I take you out all dressed up?”

The very thought made Dhiren shudder. “I couldn’t Demongay. I just wouldn’t have the courage.”

“Go on! You’d look great!”

“I’m sorry Demongay. Please don’t make it a bone of contention!”

Demongay admitted defeat, albeit temporary. “OK then. We’ll compromise. Put your best dress and heels on and come over for dinner to my place tomorrow. I could pick you up. You wouldn’t have to walk very far in the open.”

Dhiren was very reluctant but his reticence began to fade as the level of the bottle of wine in front of him gradually emptied. He agreed, on condition that it was pitch dark when Demongay picked him up and Demongay parked his car as close to Dhiren’s flat as possible.

Demongay walked Dhiren home. Again they stopped at the high wall near where Dhiren lived. This time Demongay didn’t need to ask. He held Dhiren tightly around his slim waist, pulled him toward him and kissed him deeply, his tongue entering Dhiren’s mouth. Dhiren felt dizzy, not only with the drink but with the intensity of Demongay’s passion. “I’ve never met anyone like you, Dhiren honey. I feel so good when I’m with you. You’re so sweet.”

“I feel the same about you, Demongay. Dhiren rested his head on Demongay’s shoulder, sorry that their evening together was at an end. They parted. Dhiren felt on cloud nine. Never had he known happiness in his life. Now that he was experiencing this emotion, he didn’t really know what to do with it.

When he awoke the next morning — it was Saturday — Dhiren immediately regretted allowing Demongay to persuade him. A knot of fear began to develop in his stomach at the idea of stepping out into the open air dressed as a lady. But he had agreed to and he wasn’t one to go back on his word. Anyway, it would be dark; maybe no-one would even see him, let alone recognise him.

Dhiren fussed and fretted about what to wear on his first outing as a lady but eventually settled on an elegant black dress, with a hemline just above the knee. He also put on some fancy lingerie, black stockings, and a pair of black stilettos. He rounded off his look with a nice chain necklace with large links. He decided to pull out all the stops, and even put on some false nails and eyelashes, which he felt made such a difference.

After Dhiren had put on his make-up, he sat on the settee and downed a few glasses of wine for some Dutch courage. Eight o’clock came and the agreed-upon pattern of knocks was heard at his door. Dhiren was so paranoid he was frightened someone other than Demongay would coincidentally call and catch him in his preferred clothing. But thankfully it was Demongay. He looked Dhiren up and down and said nothing for what seemed a long time.

Dhiren took this as a sign of disapproval and his face became downcast. “You think I look ridiculous, don’t you?” Dhiren said sadly. But he needn’t have worried.”Honey, you look gorgeous. No, you do really. The only problem is…I probably won’t be able to keep my hands off you!” Dhiren smiled, took him by the hand and kissed him tenderly on the cheek. Dhiren breathed a huge sigh of relief. He had been intensely worried about how Demongay was going to take him dressed up.

Dhiren picked up his clutch bag, filled with cosmetics and other girly things. They walked down the one flight of stairs, Demongay’s arm tightly around Dhiren’s waist. Demongay opened the main door to the block of flats and they emerged into the open. Dhiren felt as if he were crossing a kind of laxman Rehka (Line)–its no going back now. The cool night breeze blew deliciously between his legs and up his dress, filling him with a sense of freedom and making him feel wonderfully feminine. He relaxed a little.

Demongay didn’t let him go, knowing how worried he was. It felt slightly surreal, Dhiren’s stiletto heels click-clacking sexily against the pavement. Several people passed them but they didn’t blink an eye at the couple. Finally, after about two hundred yards, they reached Demongay’s car. He opened the passenger door for Dhiren in a gentlemanly manner and he stepped inside, smoothing his dress under him before he sat down. He had made it!

On the short journey Demongay felt the need to give Dhiren further reassurance. “Really, baby, you have a fantastic dress sense. I can’t wait to see you in your other outfits.”Well I try to keep abreast of the fashions and what girls like to wear nowadays. I normally prefer mini-skirts and skimpy tops, but I thought seeing it was my first trip out I’d be a little more conservative.”

“Well you look like a very seductive lady. If I didn’t know better, I wouldn’t be able to tell the difference.” Demongay placed his hand on Dhiren’s leg momentarily. Demongay only lived ten minutes away. The pulled up outside quite an old but elegant block of flats. Demongay opened the door for Dhiren and the pair walked hand in hand to Demongay’s ground floor home.

Dhiren had grown in confidence and didn’t flinch when a resident came out of the main entrance right in front of them and greeted Demongay. He obviously knew him. The entered Demongay’s flat. It was neat and tidy with a nice feel to it. Everything was in its place and there was no clutter. “I’ve cooked you vegetable biryani. I hope that’s OK honey.” Demongay knew Dhiren was a vegetarian.

“I’m sure it’ll be fine darling.” The use of the term of affection was not lost on Demongay. Dhiren was becoming more relaxed and this was reflected in his speech.”Pour yourself a glass of wine while I get everything ready.” Dhiren did so while Demongay put some nice ambient music on his cd player.

Dhiren settled down on Demongay’s sofa, crossed his legs and lay back. He hardly believed this was happening to him, the born loser, Dhiren. He had found a man he fancied like mad and his feelings seemed to be reciprocated. Even better, he appeared to accept his cross-dressing without qualm.

They had a lovely meal while they chatted without reserve about their likes and dislikes, hopes and fears. Dhiren smiled freely in a way he had not done since early childhood. When the meal was finished they sat together on the sofa, holding hands, while Dhiren continued to down Demongay’s delicious white wine. Demongay abstained, knowing he had to drive Dhiren back home. You know, it’s lovely having you here Dhiren honey.”

“Thank you for inviting me, darling.” Dhiren looked up to Demongay with his bright blue eyes in such a sweet, appealing way that, after a pregnant pause, Demongay could not resist kissing him fully on the mouth. Dhiren didn’t resist. That was the trigger. Demongay continued to kiss him, but more insistently. He placed his weight on Dhiren, who lay back on the cushions. Suddenly, Demongay stopped.

“Oh, I’m sorry baby. It’s eleven o’clock. I’ll have to take you back home.” A look of sadness crossed Dhiren’s face. “Unless…that is…you want to stay here tonight?” Dhiren’s face glowed with unrestrained happiness and he cuddled Demongay as a way of saying “yes”. “In that case, I think I’ll have some wine.”

The couple drank, talked and kissed for another hour or so, until Demongay suggested they go to bed. Dhiren’s whole body was tingling with excitement. He had fantasised so often about this moment and he just couldn’t believe it was occurring in reality.

Demongay led him by the hand into his bedroom, which was as pleasant and orderly as his living room. Once there they again kissed passionately and repeatedly for a long while. Demongay’s hand eventually found its way up Dhiren’s dress and stroked his nylon clad thighs. They parted for an instant, as Demongay removed his shirt and Dhiren made as if to unzip his dress. Demongay stopped him. “Let me undress you baby.”

Demongay unzipped the back of Dhiren’s dress and let it fall to the floor. Then he motioned for Dhiren to sit on his bed while he removed his stilettos. Dhiren stood up dressed only in his lingerie and stockings. Demongay pressed him against his bare chest, then they kissed some more. “Oh my God, your skin is so smooth, so soft,” exclaimed Demongay. “You’re so lovely. I want you so much baby.” As for Dhiren, he couldn’t find the words to express his feelings. After a life of virtual sensory deprivation and crushing loneliness, the sensation of full bodily contact with a man he had such affection for was simply overwhelming.

Demongay slid his hands down the back of Dhiren’s panties, and fondled his soft, hairless buttocks with his large hands. He then unhooked Dhiren’s bra and noticed, without surprise, his budding breasts. Finally, he pulled his panties right off but left his stockings on. He then bit lightly on Dhiren’s erect nipples whilst massaging his thighs and buttocks, causing him to sigh girlishly. “Ooh Demongay!” was all he could manage to whisper.

After some moments, Dhiren responded by unbuckling Demongay’s trousers and pulling them down. His boxer shorts bulged massively at the front, revealing Demongay’s excited state. In fact, Dhiren had some trouble getting them off. When he did so, Demongay’s penis sprang up. He was already almost totally erect.

Dhiren wanted to return the pleasure and knew what he needed to do. He gently restrained Demongay and dropped to his knees in front of him. Taking Demongay’s penis in one hand, he pulled the foreskin back and began to lick the exposed gland, occasionally flicking his tongue at Demongay’s sensitive penis slit. “Oh baby, that feels so good,” moaned Demongay. Dhiren became more confident in his abilities as a fellator. He ran his tongue repeatedly over the full length of Demongay’s erection, from the base to the tip, then took him into his mouth and sucked with great relish.

Demongay ran his fingers through Dhiren’s hair as his young lover sucked and licked him for several minutes. Dhiren felt wonderful, kneeling before Demongay submissively and pleasuring him. He would have loved to have Demongay climax in his mouth, but Demongay stopped him and pulled him to his feet. “Baby, that was so beautiful,” he said, kissing him deeply and pushing him back on his bed. “I want you inside me Demongay,” whispered Dhiren.

“OK baby. You haven’t been with a man before so just relax and take it nice and slow. Tell me if you’re hurting baby and I’ll stop. I don’t want to hurt you.” Demongay turned him around so he was on his belly. Demongay placed a pillow under him to raise his bottom a little.

Demongay reached for a tube in his bedside cabinet, poured a generous measure of lubricant in his hand, and inserted his forefinger into Dhiren’s little opening. He made contact with his prostate, provoking more sighs and moans from his young lover. Dhiren had never experienced such an intense sensation. Demongay pushed in a second finger and continued to tickle his insides until Dhiren gave a particularly loud groan and spurted clear fluid into his pillow. Dhiren didn’t understand he had had a prostate discharge, not a regular orgasm, and was surprised he hadn’t lost his sexual energy.

“That felt so good, Demongay!” Demongay reached for a condom and rolled it down the length of his erection. “OK baby. Just relax. If you are hurting, tell me and I’ll stop.” Dhiren couldn’t respond but trembled with desire and anticipation.

Demongay gently spread Dhiren’s milky-white buttocks and placed the tip of his erection against Dhiren’s tight anus. He pushed it in, millimetre by millimetre. Dhiren tensed his muscles against the onslaught but gradually relaxed. Eventually his sphincter gave way and Demongay was fully inside him. “How does that feel, baby?” asked Demongay. “It hurts a little but it’s OK.”Very slowly and deliberately he withdrew and re-entered Dhiren several times until he felt Dhiren had got used to him and he could thrust a little quicker and harder without hurting him.

“Oooh Demongay. That feels nice. Please don’t stop!” At each stroke Dhiren felt something like a bolt of electricity travelling up his spine. It was extremely pleasurable. Demongay quickly established a rhythm of hard thrusting and they continued this way for several minutes. Demongay then decided it was time for a new position. He pulled out of his young lover and laid him on his side.

He then pushed inside him once again and continued his thrusting. It was nice because Demongay could do this and kiss Dhiren mouth to mouth at the same time. Dhiren was really enjoying it now. Demongay’s powerful hands held him by the hips, and Dhiren could not have escaped even if he had wanted to. He felt deliciously vulnerable as Demongay pounded into him, his thighs slapping against Dhiren’s buttocks at each stroke. They were both now moaning unrestrainedly.

After a few more minutes Demongay stopped and asked Dhiren to get on top of him. Dhiren sat on Demongay, facing him, and began to move his bottom up and down on him whilst gripping Demongay’s shoulders for support. Now and then he wriggled his bottom sexily, which sent Demongay crazy with pleasure. Demongay felt his climax approaching but wanted Dhiren to come at the same time.

He began to rub Dhiren’s foreskin rapidly. This was too much for Dhiren, who groaned and spurted his semen copiously over Demongay’s chest. In turn, Demongay held him firmly around the waist and gave two or three tremendous upward thrusts. He cried out noisily as he orgasm ecstatically inside Dhiren. Dhiren collapsed upon Demongay and the two crushed their naked, spent bodies together. The sensation was incredible.

They lay thus for a long time, then once again began to kiss and caress one another.”Thank you honey,” said Demongay. “That was wonderful.” “No. Thank you, darling,” insisted Dhiren. “You’re a lovely man.” They snuggled up in bed together and fell into a deep sleep with Demongay’s arms around Dhiren. This time there were no nightmares for Dhiren. He had slept ever so soundly in the arms of his lover.

He woke up first and opened the curtains slightly. The bright sunshine streamed into the room. Demongay was still sleeping soundly but Dhiren wanted to make love with him again when he was finally awake. After that, who knows? The day was full of possibilities. For the first time in an age, Dhiren was looking forward to the day ahead. Kindly revert back with your comments to to encourage me posting me more stories.

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About a week after my first amazing session with Ann, the neighbour from downstairs who blackmailed me into modelling her lingerie, I was again accosted by her on the stairs.“Hi,” she said, coming out of her front door as I was passing. “I’m glad I bumped into you” (I knew she was lying in wait behind the door watching out through the spyhole) “are you doing anything on Wednesday night?”I said I wasn’t and she said that as John and Ian (her husband and son) were going to Aberdeen to watch the...

4 years ago
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Cross dressing gay fantasy

I would wear black stockings and no other clothes. My whole body would be shaved. I put on cream that makes my skin look even whiter and blemish free. I want my skin to look as feminine as possible. I would wear a jet black wig like a messy bob. One were I can pull the hair over to partially cover my face. I would wear oversized black sunglasses with dark red lip stick and maybe some temporary acrylic nails. I sit on top of the kitchen work top with my knees up at my chest and feet crossed...

4 years ago
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Cross dressing first time out

Now I had been seeing mike for a few months now and the relationship was going well. He had introduced me to paul he work friend for a three some which was amazing and the dressing up was getting more and more kinky!!! He hadn't never pushed the boundaries with me kept it simple and sweet, until now!! I always did as as he asked to a point, never anything abusive or nasty he knew what I was into. So when he asked me to dress up and go to a night club i was shaken and a bit scared!! I had never...

3 years ago
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cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sl**ping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

4 years ago
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cross dressing fantasy i didnt know that i had

went on a stag holiday to ibiza with about 20 of my mates a couple of years ago.the holiday mostly consisted d**g taking copius amounts of drink and sleeping with llots of women. the main stag night was fancy dress,and id already planned before i came away id already decided that i was gonna wear i toga and my girlfriends flat gladiator sandals and go as troy.a few of us got quite pally with the girls in the appartment opposite and the daytime before the main nite out one of them commented that...

2 years ago
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A manpretty husband is controlled by his wife into dressing up as a woman and taking a male lover

I couldn’t believe that Susan, my wife of two and a half years would really do this to me. Yet here I sat in the back seat of our Olds wearing a short blue satin cocktail dress. The slinky skirt kept riding up my smoothly shaven, nylon-clad thighs to display a provocative glimpse of pretty pink lace. Susan had insisted that I dress for the costume party from the skin out. Except for the girdle which held me tightly between my legs, my underwear was a matching set in the softest shade of...

2 years ago
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Cross dressing

Hello is my story. This happened. It was the mid 80’s and I just turned 17 so I thought I would go to the mall near my home town on Long Island and go shopping with my birthday money. I was looking for clothes with and I need to use the rest room. I walked into the bathroom, and the floors were wet so when I made a turn, I slipped. I put my hand against the door of a stall that was closed as not to fall, and the door it flung open because it was not locked properly. I looked inside and a man...

2 years ago
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Cross

Darren closed his eyes and rested his head in his hands for the umpteenth time that day. How could he have been so stupid? He’d always been the careful one out of every crowd he’d been involved with. Coming from a dirt poor background, he knew the smallest thing would mar his reputation and he would be screwed for the rest of his life. His whole life, he had been a straight A student. Before graduating high school a month ago, his scholarship at Princeton had already been confirmed. One night...

Gay Male
3 years ago
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Cross Burning For Dummies

To “Hardcore” Hardaway’s way of thinking, the three snot-nosed young farts standing just inside the door to his cluttered work shed didn’t look good for much, most of all a Klan job.At first, they’d tried to act cocky, like this wasn’t no big deal. But none of ‘em said a word after seeing the cross he’d put together that afternoon. Now he was back out here trying to teach these whelps a thing or two while the half-finished can of beer he’d left inside went flat.Why in hell did Jack Tidwell, who...

Humor
4 years ago
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Crossover

Crossover Janet L. Stickney [email protected] There was never any doubt that I was going to be a girl someday. I mean, from early on I would wear pale lipstick and eyeliner with my hair usually braided. Then came the Crossover week and I was able to dress like a girl from the skin out, complete with hips and boobs. My father was a drunk that never cared what I did, and my mom was long gone so how I dressed was never an issue. I work at a small shop that makes and repairs video...

4 years ago
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Cross dressing adventures

Driving up to the house I think to myself, do I really want to do this? I met Carl at a conference about two months ago. We had a few drinks and laughs; he was pretty cool. We got drunk one night and went to his room. We were laughing and being silly when he knocked over his suitcase and a pair of pantyhose fell out. I picked them up and held them in front of me like I was modeling them. He laughed and dared me to put them on. I said what the hell, dropped my pants and put them on as he sat in...

2 years ago
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CrossDressed Fairy Tales 3 The Adventures of Pierrot

Cross-Dressed Fairy Tales Part 3 By Dawn DeWinter In parts 1 and 2, Sherry and Sadie, two married men, went to a lesbian bar on their "girl's night out." There they came into the clutches of Mike and Big Sue, and are in danger of being raped - or worse - if Sherry cannot keep Big Sue entertained with "original" stories. This task has just become a mite more difficult with the arrival of two more people. Can they too be kept satisfied? Part 3 is based on Pinocchio, the story of the...

3 years ago
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Crosstraining

Cross-training Belladonna "Are you ready, pet?" "Yes, mistress," George Bloom responded as Celene knocked upon the iron door. George heard the loud clink of the old fashion knocker upon the door as he pulled at the hem of his short skirt. He anxiously waited for the door to open, hopeful that he would not be noticed by those passing by on the street below the staircase leading to the porch he was standing upon. George had never been to a Dom-sub party like the one that his...

1 year ago
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Cross dressing with my sister

I turned up at my s.....s flat, ready for a Friday night out. We got the drink flowing and started to get dressed up for the night. Pru said that she was going to wear knee high leather boots, a short skirt that will show off her ass and a top to die for. I said " what the heck do I wear that will make me stand out".pru stood there in her robe and said " let's dress you as a girl, that'll make you stand out!I jumped at the chance to get dressed as a woman,.She looked into her draw and came...

3 years ago
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CrossFeed

Cross-Feed --------------- This is the first story I've written in a while. I have started several stories, but put them on the back burner because I just can't find a good ending for them. I always want to get a story 'just right'. Anyway, here's my latest installment. There is really no TG or cross dressing in it, but I feel it belongs in the genre in a weird sort of way. I hope you like it. --------------- He was a stallion, and she rode him hard. He did not...

4 years ago
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Crossdress dreams come true

A seductive CD fulfills some of my secret fantasies. And I bring him pleasure into the bargain.Jeez, you bust your ass all year to be among the top sales people so you can get invited to the annual conference. Supposed to be in Hawaii or Vegas or somewhere exciting. And what happens? The company needs to save some money and holds it in the city where it's based. Cincinnati. For fuck's sake. I nearly didn't bother but there'd been some lay-offs already this year, so I decided I should go. You...

3 years ago
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Crossdressed By Friends 8211 Part I

I have been cross-dressing since the age of 15. I like to wear saree, suits and lehngas. This is a story about me getting dressed up by my friends when I was doing my engineering. My group in college consisted of 3 guys and 3 girls. The girls were all staying at their places and I had rented out a place in the city with my relatives. Two of my other friends used to stay in the boys hostel. This incident happened in the third year about a month before the exams when the guys had gone to their...

Gay Male
2 years ago
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Crossdressing self bondage in an empty apartment

Tonight is the night that I am going to try a daring crossdressing self bondage experience that I have been planning for some time.First of all I start with my complete feminisation. As I am going to be a total slut tonight I apply my make-up accordingly. Once I have applied foundation and powder, I use a dark eye shadow to give me a smokey eye look. Then black eye-liner under the eye and I apply long false eye-lashes. I paint my lips a deep red and then lip gloss on top, making them full and...

2 years ago
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Cross dressing sissy transgender car shopping

Car Shopping I could never repay mom for what she has done for me in the way she accepted and encouraged who and what I am. Being successful in my career has allowed me to come from a small mobile home in a rundown trailer park to my current life style and affords me to do things for he. So, two Years ago on Mother’s day I wanted to do something special. I got her a brand new car. Not knowing anything at all about cars (know lots about dolls and fashion) I asked a friend (Gary) to go with me...

1 year ago
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cross dressing fun turned sour

A few nights ago, one of my pals whom I have some great fun with, said he had tickets for a great Hypnotist would I like to go? Of course, I agreed and off we went. Shit, the show was awful. He picked on me as one of the last clients, should I say. He dragged me on stage (no pun intended) and tried to put me under. I knew he didn't succeed, or so I thought, Tom, my mate, waited until I returned to my seat. “Load of crap” I told him. “Ah” said Tom “You did not see what we, the audience...

3 years ago
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Cross Dressing In Goa 8211 Part 1

I am Sumit, a regular reader and fan of ISS. This is my first time so kindly ignore spelling mistakes. I am a19 year old chubby boy. I am fair and 5 feet 4 inches tall. This incident happened when I went to Goa with my friends. After semester exam, my classmates decided to visit Goa to relax. We reached Goa early in morning. Everybody was tired because of 8 hr train journey in general compartment. We all had breakfast and decided to take rest. After a while we went on beach. We played football,...

Gay Male
2 years ago
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Cross Dressing Bus Journey Fun

Hi All, This is Vinnie Cd here. 26. I love wearing short skirts panties and thongs a lot. I wear nice laced panties to work many Times too. Had a nice time even with couple of cab guys thanks to my cute girly ass in frilly Panties. I love sucking and getting fucked outside. It really makes me horny n slutty. Last year, I was travelling to pune in a bus and was wearing thongs sports bra a loose Tee-shirt and jacket tracks outside. I also wear a nice girly deo. It was sleeper and I got in And got...

1 year ago
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Cross dressing gay fantasy act 2

He then walked into the room. He was already naked. I seen him behind me in the mirror. Those bulging biceps. That lovely barrel chest. I was getting a semi. I had told him what I wanted to try. He of course was up for it. I was a bit nervous about it. I'm sure He wouldn't hurt me. At least not on purpose. One last look in the mirror before standing up and moving to the bed. I lay on my back, raised my legs in the air, put my knees back towards my chest before extending my ankles over my head....

2 years ago
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I Fucked My Girl Friend In Front Of My X Lover

hi friends i am Krishna from Vizag (Andhra Pradesh ) what i am saying is a true story which happened the day before yesterday my girlfriend name is Madhuri it’s her true name no name change and all and my x lover name is Anusha.i asked my x lover for sex but she refused that one time i forced to do so she left me; that time i got angry so i wanted to take revenge so i got my contacts and selected one of them and flirt her and made my girlfriend and said that before i use to have lover and now...

3 years ago
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Wifes Weekend Lover

I am going on a hunting trip over a long weekend mid-January, the weather is turning cold and my wife decides to stay home instead of spending the weekend in the camp. Old houses are not as warm as home. Since discovering my online activity she has begun to have some online fun herself. As she begins to read some stories and read some profiles she realizes most of the people on the sites are like us and looking for something to add a little spice and variety to their sex lives.As she becomes...

Wife Lovers
2 years ago
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Turned Out By My Wifes Lover

"Trish, I think this is taking it all a bit far," Joel complained to his wife. Trish was Joel's wife of 8 years. She was watching Joel take a scented bubble bath. She had him shaving his underarms. They were the last body hair remaining on Joels's body, after she'd instructed to him shave his entire body. Trish had helped out with any areas he couldn't reach. Trish smiled and laughed gently. She reached down and stroked Joel's erection. "Honey, this tells me something different....

2 years ago
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DADS BABY AND LOVER

It was raining outside, Cats and Dogs, so Thomas Baxter sat on the porch, knowing Angel would be home soon. She hated thunderstorms, they had terrified her ever since she was a little girl. Even when Grandma would tell her thunder was just "Angels bowling, honey", Angel would roll her eyes back in her head in disbelief.Bethany came out on the porch and smiled at her son. "Waiting for Angel to come home early from work, dear?" she smiled, putting her hand on his shoulder. He looked up at his...

3 years ago
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A Dark and Deadly Lover

Carla sighed in frustration as she scanned the packed nightclub. He just was not here, she growled silently. Every man she looked at did not attract her in the least, too skinny, too heavy, too blond, too redheaded. Not that she had any problem with the later; she was just in the mood for a dark haired lover tonight. Weaving her way through the mass of undulating bodies as they danced, drawing angry or jealous stares from the women, ogling drools from the men, Carla ignored them all. She was...

2 years ago
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Crossroads RulesChapter 5

Sid arrived in class early to watch the arrival of Cynthia. It was her grand unveiling - the first day in which she was going public, wearing her new wardrobe. He wondered which of the new outfits she would wear. He hoped that it was the blue dress since it was the sexiest of them. When Cynthia glided into the room, even Sid was surprised at the transformation. The loose fitting blue dress came down to her knees, was tight at the waist, and had a plunging neckline that just begged a man to...

2 years ago
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Cross One Mans Journey into Darkness Part One

No light reached this part of the room. The solitary sunbeam that had managed to poke its way through the curtains fell on a dirty heap of ripped up clothing in the far corner. But here, there was only darkness, and the ragged breathing of the room's sole inhabitant. Tyler lay naked, his arms and legs strapped to the corners of the bed with leather belts, allowing him no room to move or stretch his sagging limbs. Premature wrinkles lined the strong, angular features of his now gaunt visage....

Supernatural
3 years ago
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Marcy Takes a Lover

Marcy Takes a Lover byFurryDevil©Disclaimer: This story is about a white married couple finding a black man for the wife to have sex with. It is completely consensual on both of their parts, and therefore is just good, clean, fun. If you don't like this kind of thing, you should probably find something else to read. *My name is Marcy and I have something I need to get off my chest. I live just outside of Detroit, but I was on a "weekend getaway". I still can't believe what I had gotten myself...

1 year ago
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You Know This Lover

You drive through the night, the only sound your tires singing on wet black pavement and the rhythm of your own heart. You watch your small hands griping the steering wheel so tightly your knuckles are white with anticipation. You are amazed, why should you feel this tension? You have done this many times. This is no new experience, you know this lover. This is no single night’s lust with a stranger. This is more than your lover you meet this is your love. But then you think. "Can I ever know...

Erotic
1 year ago
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Consequences of Cross Dressing

Consequences of Cross Dressing by Cindy Johnson ([email protected]) My dilemma was that I masturbated all over mother's gown and nylons and I frantically tried to clean everything up as fast as possible. I was frightened that it would leave a stain and I didn't know what to do but after twenty minutes of cleaning everything with soap and water, I felt like I was in the clear. I put everything back where it I found them and ran to my room reflecting on what had just happened. I...

2 years ago
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Marcy takes a lover

My name is Marcy and I have something I need to get off my chest. I live just outside of Detroit, but I was on a "weekend getaway". I still can't believe what I had gotten myself into this time. I was standing in a hotel room in Boston, getting ready to go meet a black man that my husband had found for me online, a black man that I had already agreed to have sex with.I'm 34 years old, and I've been married to Jason for 11 years now. Jason is 2 years older than me, 5'11" tall, and is in pretty...

4 years ago
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With My Lover

Hi friends I thank you for the overwhelming response to my previous stories, my mailbox is flooded with your love and that motivates me so please keep them coming here I am posting one more story I hope you will love it too, mail me your comments and requests on and add me on yahoo I once again want to tell you all that all my stories are fictitious so please do not mail me asking the contact info of the girl just read enjoy and appreciate Rashmi looked into the rearview mirror of her minivan...

4 years ago
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Sarahs Teen Lover

Sarah is a sexy housewife in her early 40's that has spent her entire 20+ year marriage cuckolding her very happy husband. She decides that she wants to try out some "young stuff" and hubby is more than willing to help her find a new lover! ***Sarah and I have been happily married for about twenty years now. We have raised our c***dren and find ourselves now in our mid-forty's. We are still both in very good physical condition and enjoy a freedom that most couples our age are quite envious...

2 years ago
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A chinese wife decides to have a lover

I and Tanya had been car-pooling for about a year now. She and I work in an office and live close to each other and carpool three days a week. Tanya is 41 years old Chinese wife with a handsome looking husband and a beautiful 18 years old daughter. After some time we would have chat on various topics, one day I told her I like women who wear dresses/skirts/blouses that show her curves a little. This was just an innocent remark. A few days later, it was my turn to drive, she parked her car in...

3 years ago
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Going Nova ch 3 The Dressing Room

The knocking persisted and Hazel croaked sleepily, “Honey, will you go see who that is?” Warrick sighed, sat up in bed, and stretched. He knew full well who it was. He rubbed his hand lightly on his wife’s naked back for a moment, thinking fondly about the previous night, and then got up to put on his bathrobe. He smoothed his bedhead over as he descended the stairs to the door. When he opened it, Elsie burst inside. “Hey Warrick! Is Brie awake yet?” she asked brightly. “Elsie, it’s far too...

3 years ago
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How it really is for hubby when wife has a lover

I just wanted to share this with the guys, as what you think you want may not be what you want. I’ve been very lucky in my marriages – been married more than once and each of my wives liked to play, although at different levels. My wife and I are older now, but both of us have experienced threesomes with extra males in our bed and we found we preferred longer term relationships with an extra male for her – it kept her feeling good and kept me horny. Speaking only of my current wife of 30 years,...

4 years ago
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Pleasures at Dressing Manor part 7

Pleasures at Dressing Manor - by PRIM The story so far: Young teacher Miles Johnson has tried his best to rescue his pupil, Lyndon Blonding, 18, from the sissifying plans of his spiteful stepmother, Vera Hidebotham, who aims to turn her stepson into a girl. His Headmistress, Alison Forceman, accompanied the young teacher to the boy's home, Dressing Manor, outwardly to help him but secretly in league with Vera. The two males have been fed the feminizing drug Fem-Agra,...

2 years ago
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Lover

She said she was going to take a lover. We were sitting at the dining table for dinner when she told me. I did not even hesitate before I answered. I said “OK.” This is a story of someone who finally had enough of the social climber world heaped on him. I am Jack (short for Jackson) Walden, 34, married for 12 years. I am a very successful inventor and technical writer. I own a small manufacturing plant. That stuff doesn’t mean much to me. Money is just a scorecard, and I ain’t playing the...

3 years ago
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Dressing Phase 1 A Holiday in Venice

DRESSING: PHASE 1 - A HOLIDAY IN VENICE Barry Robbins and I have been best friends since we were three years old and met in the Reception Class at Nursery School. Naturally as two active, competitive little boys we had our moments and our spats, but it soon became clear to our parents and teachers that we functioned better together than apart. As we grew up it was apparent that our talents and personalities complemented each other. Barry was the imaginative one; I could come up with...

1 year ago
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The Vampires Lover

Vampires. They're the lords of the night, the stalkers of the living. Each one was an irresistible pale beauty with powers far greater than any creature who lurked in the darkness. With one simple gaze they can trap you in their lustful spell and turn you into a mindless puppet. They held the strength of ten men and the speed of a cheetah. For countless Centuries, Vampires reigned dominion over lands, towns, and kingdoms. Villages have paid them tribute in exchange for safety. They were truly...

Anal
1 year ago
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Policewoman And Her New Lesbian Lover

Last Friday I was still in my police uniform when Gretchen’s motorcycle roared as she drove into my driveway. My 43 year old new found lesbian lover had arrived and I knew I was in for a long passionate night. I had become bi-sexual after my divorce, I wanted to try women and found out I preferred the tender lovemaking and soft body of a women. I had no problem attracting women, I knew I was still hot for a 34 year old, I had the large body of a full figured Scandinavian women, I am six feet...

2 years ago
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Thanksgiving With My Lover

My heart was light and I was filled with excitement! I was finally leaving the plane that had taken me from my home to Austin and my lover! As I walked down the plane's aisle, fresh cum from my favorite cab driver still oozing from my pussy, my excitement at finally seeing Tyrone again had me jumping out of my skin! It had been a couple of weeks since we'd been together and, even though I'd had plenty of sex from others, my heart and my body craved to be mated to him; to be one with him....

2 years ago
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Super Lover

Super Lovers Story by Angela J. ([email protected]) Editing by Steve Zink ([email protected]) Episode 1 "The Beginning" "Legend tells of two super beings, one male and one female. Their powers were derived from their super suits and each other. The suits were designed for two lovers. The lovers, wearing their super suits, made love in order to temporarily obtain their super powers. Together they were invincible. Apart and alone, they would fail..." I quickly got bored with...

3 years ago
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Crossroads A Young Hero

I walked through the headstones towards Dad's car. It was my car now after that accident. I was walking away from the double funeral for Mark and Carol Arrowstone. It was less than a week ago that I had come home to the cops sitting in my driveway to tell me that Mom and Dad had been in a car accident. The drunk driver that hit them was dead too. Standing next to the car was Mike Larter, Dad's lawyer. He was handling the reading of the will and the distribution of my parent's assets. I knew...

3 years ago
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Brittany in the Dressing Room

She didn't understand what she was doing here, in JC Penny on a Wednesday afternoon. Her long distance fucktoy, Jordan lived on the east coast. She had, of course, sent him dirty pictures from dressing rooms while she shopped before; usually Victoria Secret dressing rooms. And she had even played with herself in a dressing room while he watched via Facetime. But every one of those times was in a store of her choosing; he had never before specified where she should go. What the fuck was going...

Toys
4 years ago
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Mom fucked hard by lover

I remember a couple of years ago when I was home alone with my mom. My dad was gone for the evening, I cant remember why.My mom kept getting textmessages that she was trying to ignore. Suddenly her phone rang. My mom g****d it and went outside. Curious I opened the window slightly to listen to the conversation."No, not tonight, Its too late" The window made a noise and my mom noticed me. "I got to go" she ended the call with."was it dad" I asked, knowing that was not the case. "It was from...

2 years ago
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My Papa My Lover

” Kuki, I will be visiting Banglore today at 8 pm. Darling, I am on my way to Sri Lanka and my plane is leaving for Sri Lanka two days after. I thought I would spend some NICE TIME with my darling daughter. I cant wait for time to pass. How is Raman? I hope he is taking care of my DARLING!” Papa was saying on the phone as I had just stepped out of the bathroom. I had a small towel round my waist, water dripping from my wet body. As I heard my Papa speak to HIS DARLING DAUGHTER, her pussy was...

Incest
1 year ago
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His Wife Their Lover

"You can come in now!" Tony wheeled Tim into his wife's bedroom. Belinda lay on the bed, with one hand she turned the pages of her album while touching herself with her other hand. Her warm body softly undulated. The pattern of her panties concealed the finer details of her sex, but not the size nor thickness of her smooth, shaven vulva which stood out like a hot, swollen tumulus. He enjoyed the humiliation that his wife put him through, including the unconventional taste she had in men....

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