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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