A Surprise Gift

Author's note: As with all my stories this is a fantasy, possibly set in a parallel universe. I hope that you enjoy it and please comment if you'd like another chapter to this story.

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Julian Carter was a closet cross-dresser since his teens. The feeling of women's clothing felt so sensual on his skin. He'd had his fair share of girlfriends but they usually left him when he showed interest in wearing women's clothes. That is, until he met Peggy.

Julian and Peggy just clicked when they were introduced by mutual friends. They became very good friends and laughed a lot when they were together. They soon started dating and having sex. At first it was vanilla sex but then they soon started fellatio and cunnilingus sex.

Julian noticed that Peggy would savour his semen after she gave him a blowjob. She sometimes kissed him after eventually swallowing his come. At first he resisted bit then he noticed that his semen didn't taste bad. In fact he liked the taste of his semen.

Julian noticed that Peggy would often slip on some panties after he came inside her vagina. He questioned her about it and she answered "I don't want to waste it." Julian decided that it wouldn't be a waste if he performed cunnilingus on Peggy after he'd come inside her, so he did that. Peggy seemed delighted and Julian regularly ate his come out of Peggy.

Peggy soon asked Julian to have anal sex with her and, although it wasn't as often as Julian would have liked, Peggy regularly douched herself, which led to Julian buggering her.

Julian had been dating Peggy for nearly a year when he asked what it was like wearing women's clothes. Peggy didn't baulk at his question and offered him her undies to wear. It became a game: he would wear her undies and that often led to sex.

To Julian's delight, Peggy suggested that he could wear a wraparound, Fijian-style, sulu skirt at home in summer. Her excuse was that it would be cooler than shorts, and it was, surprisingly. Peggy also suggested that Julian could wear pantyhose under his jeans in winter -- it would help keep him warm. It became common for Julian to wear female undies at home with a skirt in summer and pantyhose in winter.

For fun, Peggy slowly introduced Julian to wear her clothes: suspenders and stockings, blouses, summer dresses and sandals. Julian always became excited when Peggy suggested that he wear something of hers, after all, they were the same size and body shape, except Peggy had beautiful, firm and perky 'A' cup breasts. They practised Pilates together to keep themselves fit and slender.

Peggy then suggested that Julian's hairs looked ugly in her stockings and so Julian jumped at her offer of using her epilator to remove his body hair. It hurt a lot as his hairs were being pulled out at their roots but the sensual feeling of a hairless body felt exquisite, so it was worth the pain. They had exception sex that weekend.

Peggy called Julian, Jules, and then she jokingly called him her girlfriend. It became a private joke that Jules was Peggy's lesbian lover. Peggy even called Julian, Jules, in public, and why not? Jules was a unisex name. They're was of course the famous, male writer, Jules Verne. Julian loved Peggy calling him, Jules. Their private joke made him feel like a sexy lesbian.

Peggy started to call Julian, Julie. She said it was his alter female ego. Julian felt like he was in heaven: they had great sex, his girlfriend encouraged him to wear woman's clothes and she called him, Julie.

They wore conventional clothes to their wedding, except for the female panties and camisole that Julian wore under his three-piece suit. However, after the wedding, Peggy dressed Julian in Peggy's wedding dress, corset, stockings, high-heels, and veil, and Julian sashayed around their hotel room. They then had fantastic sex until the early hours of the morning. It was the first time that Julian wore outer, female clothes other than at home, albeit still in the privacy of their hotel room.

Julian wore female clothes only at home, in private and mostly on the weekends. Julian did wear a camisole to bed during the week but he wore men's clothes to work, albeit with women's undies. Their sex life was passionate and Peggy joked that she loved having sex with her lesbian wife.

One weekend, Peggy asked if she should peg her wife. Julian was ecstatic but displayed a concerned look. He allowed Peggy to convince him to try it and they could stop if he didn't like it or if it hurt. Of course it didn't hurt and Julian loved being pegged, so Peggy regularly pegged Julian. Peggy bought a set of butt-plugs for Julian to wear on the weekends to "Stretch his boi-pussy." That would help Julian take bigger dildos inside him.

A month or two later, Peggy suggested that Julian could try taking different herbs to help his pecs grow. She also bought him breasts pumps to encourage his breasts to grow. Julian was enraptured when he first noticed that his breasts were sensitive and Peggy announced that his breasts were budding. She bought him a training bra for him to wear at home.

Over the following year, Julian's breasts slowly grew into perky, 'A' size cups. At first he wore Peggy's bras but then Peggy brought home some sexy bras for him to call his own.

Julian's wardrobe expanded: undies, bras, suspenders, stockings, blouses, skirts, dresses and even stiletto pumps. He wore them on the weekends and Peggy loved spending time with her lesbian wife, Julie. Julian hid his breasts in public by wearing a compression vest, loose tops of a three-piece suit to work.

One Saturday, Peggy said "Julie, why don't you get dressed? I have a surprise for you."

This was code for Julian to dress his best as a woman and a surprise usually meant a new sex toy or some new sex position. No matter what, it usually led to fantastic sex.

Julian took about an hour to get ready: he douched; epilated his body; bathed, applied makeup, which Peggy had showed him how to do it properly; put on his best, blond wig; dressed in suspenders and stockings; see-through black undies; a sexy, lace bra; a short, pleated skirt; a see-through, white blouse and topped it of with black, 7.5 cm, stiletto pumps.

Julian sexily pranced into the kitchen and stopped dead. There was a man, a big man, standing next to Peggy. This was the first person to see Julian dressed as a woman, except for Peggy. He slowly looked from Peggy to the man, backwards and forwards. Horrible things raced through his mind: was this Peggy's way of dumping him for another man? Was she going to have sex with this hunk of a man? Was she deliberately embarrassing Julian?

"Julie, this is Roy. Roy, please meet Julie." said Peggy with a smile on her face.

"How do you do, Julie." said Roy.

Julian continued to look from Peggy to Roy and back again. Peggy moved closer to Julian. She hugged him and drew him towards their very sturdy, kitchen-table -- they'd often had sex on it so he knew it was VERY sturdy. She kissed him and whispered in his ear "Roy is you're surprise, Julie. I thought that he could help you feel like a real woman. Don't be rude. Please say hello."

Julian was relieved. His horrid thoughts were wrong. Peggy was giving him a surprise, a big surprise. He wasn't sure that he was ready for such a surprise but he said, in his best female voice -- Peggy had shown him some online videos to watch and he practised until he had very convincing feminine voice -- "Hello... Roy."

Julian still faced Peggy as she leant against the kitchen table. Roy was behind him. Peggy said "Roy, Julie's wearing stockings. Would you like to see the top of Julie's stockings?"

"Yes please." answered Roy. Julian thought that Roy sounded like a gentleman.

"Let me show Roy the tops of your stockings, Julie." said Peggy, as she caressed Julian's cheek.

Julian felt himself relax as Peggy caressed his face he nodded slightly and Peggy slowly lifted the back of Julian's skirt. Julian felt the skirt's hem softly brush against his stockinged thighs and then his bare skin above the welts of the stockings.

Roy sighed and said "You have very beautiful legs, Julie."

Julian was confused. He enjoyed Roy paying him comments but was still a little embarrassed about wearing women's clothes in front of a stranger. He looked at Peggy, who smiled and nodded.

Julian bit his lip and softly said "Thank you." Peggy smiled and further caressed his face. He felt Peggy's approval and felt more relaxed.

Peggy moved her right hand from Julian's face and slid it under Julian's skirt. She fondled his testes through his sheer, see-through undies. She rolled his testes around like hard boiled eggs. Julian felt his resistance and concern slacken. He loved how Peggy fondled his testes. He knew that she knew that it would get him aroused, and of course, it did.

Peggy fondled Juliana testes, slowly at first, but then faster and harder. She used both hands to fondle his testes, one hand on each testicle. She pressed his testes between her fingers and thumbs. If his testes were boiled eggs, they would have started to break apart by now. She kept fondling and Julian's testes were hurting, exquisitely.

Julian leant forwards as Peggy squeezed his testes. He was getting very aroused. He felt pre-ejaculate seeping out of his penis. He was surprised that he was only semi-hard but that may have something to do with a stranger's presence.

"Julie's wearing very sexy undies, Roy. Why don't you have a look." said Peggy, as she squashed Julian's testes.

Julian felt Roy lift up the hem of Julian's skirt. Roy said "Oh, they are very sexy, very beautiful."

"Do you think that Julie has a sexy derriere, Roy?" asked Peggy.

Julian felt Roy lift his skirt and gently place it on his back. Roy said "A very beautiful derriere."

"The material of Julie's undies are very soft." said Peggy, as she continued to crush Julian's balls.

Julian felt Roy's big hands, gently caress his buttocks. He was surprised at how gentle Roy was as Roy's hands caressed his buttocks.

Peggy whispered into Julian's ear "I think Roy wants to fuck you, Julie."

Julian begged with his eyes and shook his head.

Peggy gently kissed him and whispered "Every woman needs to lose her virginity, Julie. It makes her feel like a real woman. Roy's going to make you a woman, Julie. Don't you want to be my girlfriend?"

Julian did want to be Peggy's girlfriend. They had a wonderful time role-playing as lesbian girlfriends. He slowly nodded. Peggy said "Would you like to see Julie's naked buttocks, Roy."

"Yes." answered Roy. Julian thought that he could detect lust in Roy's voice.

Julian felt Roy gently slip Julian's undies off his buttocks. Roy caressed Julian's bare buttocks.

Peggy squeezed Julian's testes. If they were boiled eggs they would have been completely destroyed by now. Peggy crushed Julian's left testicle and then squeezed it like squeezing a seed out of a cooked cherry. Julian's testicle shot up into it's inguinal canal. Julian buckled forwards and consequently pressed his buttocks against Roy.

"Oops." said Peggy with a giggle. "Lost one."

Peggy concentrated on crushing Julian's other testicle. Julian almost cried out in pain and then Peggy popped it up into its inguinal canal. "There's goes the other one." said Peggy and then giggled.

Julian buckled forwards and placed his elbows on the table. He grabbed the edge of the table with his hands. The pain was exquisite but was now receding. His buttocks were pressed firmly against Roy.

Peggy said "I think Julie's ready, Roy. Here's some lubricant." She passed the bottle of silicone-based, anal lubricant to Roy. Julian hadn't noticed it sitting on the table.

Julian heard Roy squeeze out some lubricant. He felt Roy smear it over his buttocks. It felt so slippery. Julian felt Roy spread the lubricant over Julian's buttocks. Roy used his thumbs to work the lubricant closer to Julian's cleft. Julian felt Roy's thumbs slide up and down his crack. Julian shuddered and puckered as Roy slid one thumb and then the other over his anus.

Peggy slowly caressed Julian's penis and it finally started to get harder. The slippery fabric of Julian's panties felt so sensual as Peggy slid her fingers over his glans and shaft.

Roy kept sliding his thumbs over Julian's anus. On each pass, Roy pressed just a tiny bit harder. At first, Julian clenched his anus but after a while, he relaxed.

Roy pressed a little bit of his right thumb into Julian's anus and then slowly moved it away. Roy repeated the process with his other thumb. Each time Roy switched between thumbs he pressed just a little bit more of his thumb into Julian's anus. Julian loved the feeling and relaxed his anus more, hoping that Roy would penetrate him deeper.

Roy was very good at getting Julian excited. Julian thought that Roy must have done this a lot of times. Each time Roy passed his thumb over Julian's anus, it penetrated a little bit more. Eventually Roy's thumbs would press into Julian's sphincter. Julian estimated that Roy's thumbs were entering him up to the first knuckle.

Roy asked "Are you okay with this, Julie?"

"Yes." sighed Julian.

Roy's thumb penetrated through Julian's sphincter. Roy pushed his thumb past the first knuckle through Julian's sphincter. It felt like a little butt-plug to Julian and then Roy pulled his thumb out again. Roy pushed his other thumb through Julian's sphincter and Julian's anus gripped it as the knuckle slipped past Julian's sphincter.

Roy continued to penetrate Julian's anus with alternating thumbs. Julian felt her sphincter relax until his anus gaped in-between each penetration of Roy's thumbs.

Roy paused a little bit before removing one thumb as he pushed in his other thumb. Julian could feel his sphincter being slowly encouraged to stretch wider and wider. He allowed his sphincter to relax.

After what seemed like hours to Julian, Roy was able to slide both thumbs into Julian's anus. Julian felt Roy rotate his thumbs around Julian's anus, stretching Julian's sphincter wider. Julian felt his anus gaping.

Once Julian's sphincter was completely relaxed, Roy removed one thumb and squirted the lubricant through Julian's gaping anus, deep into Julian's rectum. Julian sighed as the cold, super-slippery liquid penetrated deep into his bowels.

Roy continued to stretch Julian's sphincter with his thumbs as Peggy continued to slowly stroke Julian's shaft.

Roy held Julian's arse open and asked "Do you want this, Julie? Are you ready for me?"

Julian opened his eyes to see Peggy smiling at him. She nodded. Julian whispered "Condom?"

Peggy whispered "Roy's got a certificate to say that he's disease free. Don't you want to feel his come inside you? Most women love the feeling of semen inside them."

Julian slowly shook his head. Peggy smiled and slowly nodded her head. Julian felt himself slowly agreeing with Peggy and ended up nodding with her. Peggy caressed Julian's cheek with one hand as she stroked Julian's shaft with the other.

Julian closed his eyes. It was time to decide. He desperately wanted to be Peggy's lesbian girlfriend and what Roy was doing felt so good. He sighed "Yes please, Roy."

"What do you want, Julie?" asked Peggy, prompting Julian to talk dirty.

Julian couldn't bring himself to talk dirty to a stranger but he did manage to say "Yes please, Roy. Please fuck me, Roy. Please fuck me till you come."

"Who could refuse such a well-mannered request." said Roy.

Roy removed his thumbs and Julian felt empty. He kept his anus relaxed and gaping, knowing, hoping that Roy would replace it with his penis.

Julian realised that he hadn't seen Roy's penis. He became anxious. He didn't know how big it was. He soon found out.

Roy pressed his glans against Julian's anus. The tip easily slipped in, but then Roy's corona stretched Julian's sphincter wider. Julian grunted. He knew from when Peggy pegged him that he had to keep breathing, so he took long, slow, deep breaths. Julian pushed against Roy's intrusion and he felt his sphincter relax. He felt Roy's glans slip through his sphincter into his rectum. He grunted again but felt relieved.

Roy caressed Julian's buttocks. Julian's thighs were pressed together holding his panties up. He felt Roy's, surprisingly, soft hands caressing the skin on his buttocks. He felt the waistband of his undies nestled in the crease between his buttocks and thighs.

Julian was bent forwards, legs held tightly together and he braced himself with his arms on the table. Peggy was squatting in front of Julian and still played with his penis. Roy's glans was inside Julian's arse. Julian slowly pushed his backside towards Roy and he felt Roy's shaft slide further into his rectum.

Julian sighed with pleasure. This felt much better than the silicone dildo that Peggy used to peg him. Roy's penis was hard with a soft outer part. He internally giggled, it was like the opposite to a soft-centred chocolate, which was hard on the outside with a soft, chewy centre. Julian wondered if Roy's penis was chewy.

Roy pushed and Julian's rectum spread wider as Roy's shaft penetrated him further. Julian wondered when it would stop. Roy's shaft seem to go deeper and deeper. It was so deep that Julian couldn't feel it's end. He could feel the shaft rubbing against the walls of his stretched rectum but how far past his rectum was Roy's glans?

Julian was relieved when he felt Roy's pubic hair tickle his buttocks. He felt Roy's heavy balls bump against his perineum and thighs.

Julian felt Peggy pull down the front of his undies. His gusset of his undies was still trapped between his thighs. He looked past his breasts to see, and feel, Peggy lick his pre-ejaculate off the tip of his glans. It felt so good.

Julian almost flinched when he heard Roy quietly ask "Are you okay, Julie?"

"Yes." sighed Julian, especially when Peggy sucked his penis deep into her throat.

Roy slowly pulled his hips away from Julian. Julian felt the veins on Roy's shaft massage his rectum. His sphincter was extra-stimulated by Roy's rough shaft.

Roy then pushed his shaft into Julian. Julian gasped in pleasure as Roy's shaft stretched the walls of his rectum.

Roy pulled back and pushed forwards, stimulating Julian's rectum. Julian felt his prostate being rubbed by Roy's shaft, which induced pre-ejaculate to seep put of Julian's urethra into Peggy's waiting throat.

Julian was temporarily disappointed when Peggy let his shaft slip out of her mouth. Peggy said "Why don't you feel Julie's breasts, Roy?" as she undid Julian's bra. She then continued to suck Julian's shaft.

Julian sighed as he felt Roy's strong hands gently hold his breasts. Roy pinched Julian's nipples between his thumbs and index fingers. It felt so good to have Roy's big, strong hands grasp Julian's breasts.

"They feel so good." said Roy and Julian totally agreed with him.

Roy increased his rate of thrusts, in and out of Julian's arse. Julian felt her sphincter completely relax but her rectum clamped onto Roy's shaft. Roy grunted and said "So tight."

Roy continued to plunge in and out of Julian's rectum. Julian continued to flow pre-ejaculate into Peggy's eager mouth. Julian's breasts were being massaged by Roy's hands and his nipples pinched by Roy's fingers.

Julian couldn't help himself. He thrust forwards into Peggy's throat and backwards onto Roy's shaft. It felt so wonderful. He'd never been so stimulated in so many different parts of his body. His penis was being sucked, his breasts were being squeezed and his arse was being plundered.

Roy had settled into full thrusting mode. Roy's thighs slapped against Julian's. Julian met each of Roy's thrust with his own backwards thrust. They slapped hard against each other and poor Peggy's mouth was getting a pounding.

Peggy held onto Julian's hips to help her coordinate Julian's thrust with her own as well as prevent her nose being broken by Julian's belly. Julian lost all his scruples: he didn't care about hurting Peggy's face, he didn't care about pleasuring Roy. He just wanted to be sucked and fucked.