Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. 

He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the girl he was sleeping with. 

He knew that there were men who cross-dressed. The notion of a man dressing as a woman was something that society and himself found perverse or sick, but it seemed to trouble him. So, feeling nervous and somewhat tentative, he found himself researching the subject on the net about the whole genre of cross-dressing. At first he cleared his searches on his laptop after a night of browsing, just in case he got found out, but eventually, that ceased to be a problem for him. 

Owing to the fact that his divorces had been financially crippling he found himself renting a small flat in someone else’s house. It was a basement flat with the same front door and hall but just a lockable side door to his apartment. 

The conflict of his sexuality and his love of lingerie still seemed to haunt him. He considered the idea of buying some for himself and using it as a masturbating aide. It worked. After a few wrong size purchases, he finally found out what fitted and what looked and felt good. 

So in the secrecy and sanctity of his bedroom, he dressed and found that very quickly he liked it a little too much. He decided to buy some shoes, a wig, breast forms and some makeup.

YouTube was brilliant for learning about stuff like that and soon found that he could dress up, make himself up and look at himself in the mirror getting really turned on. Johnny even admitted to himself that he looked quite passable and decided to pick out a sissy name. Carrie sounded good and he liked calling himself that in front of the mirror and calling himself a slut when he got going. He was gradually becoming a sissy.

Carrie actually found that her masturbation was much better than any sex she had had with any woman. Her mind then considered the idea of having sex with a guy dressed. She could really be a woman and be treated like one.

Panic then ensued. What if anyone found out, what would they think, what would her parents think? It tortured her but she was enjoying playing with herself far too much. She even started to slide a finger up her arse to see what it felt like. It wasn’t that good at first but it didn’t take long before she actually started to really enjoy it. 

So the next step was maybe a realistic dildo. She started small but after a few months, they became bigger and bigger. Very soon she could fuck herself whilst wanking in front of a mirror, teasing her inner g spot making her orgasms unbelievable.

Little by little she started to collect up some of her cum and taste it, which very soon turned into her either cumming into her hand and licking it all off or cumming on her stomach and collecting it all up and swallowing it. This became a regular occurrence and Carrie really looked forward to having a mouthful of cum as she wanked. 

A couple of times she got questioned by friends and people at work when she hadn’t quite got all the nail varnish off. She gave a few feeble excuses about helping friends decorate and hadn’t cleaned her hands properly with white spirit. This happened a few times but after about the third time someone mentioned that it seemed funny that all her friends decorating was always with red paint. 

“You sure it’s not nail varnish and your not a secret closet crossdresser?” her housemate asked. 

Johnny/ Carrie wrote it off and made a joke about it, even being somewhat disrespectful to the very idea and quite offended. 

There was a famous quotation from William Shakespeare’s “Hamlet” that said, 

“The lady doth protest too much!” 

Her close friends became suspicious. They actually spoke about it behind her back. Little did she know that her landlord was a gay rampant crossdresser fancier and so were his two best friends. 

They decided to subtly do some secret investigation. He had a key to her apartment. After a few weeks, when the innuendos had subsided and with a sincere apology, the idea had gone. Carrie thought that she had got away with it and started using cotton buds to make sure there was no trace of nail varnish each time. 

Secretly he was just giving her time so they could prepare themselves, and check it out.  When the coast was clear, his friends crept in and searched through her stuff. What they found was startling but in a way not surprising.

Carrie had a wardrobe half full of dresses, basques, corsets, stilettos, and slips. Three of her drawers were full of stockings, suspenders, panties, a collection of wigs, a box full of jewellery and a large makeup case with everything with everything you could possibly imagine. A small bottle of Channel number 5 perfume and, of course,  several bottles of red nail varnish. 

One of his friends was a bit of a computer wiz and he went straight for her laptop and quickly worked out the password. Suddenly they had access to a plethora of evidence. Pictures, sexy videos of Carrie wanking using dildos, blogs, crossdressers websites, sexy stories and a diary of the transition from guy to a transvestite. 

They were, quite frankly, amazed, but then the general consensus became that she’d been suffering in silence and had created this whole new secret world. This was her fem side and no one even had the slightest inclination that this was her reality. 

‘Poor thing they all thought. We’ll have to give Johnny, or Carrie, a night of ecstasy.’ 

They secretly planted a tiny camera in her bedroom that was linked to their phones. They could pick the opportune moment when they would give Carrie the night of her life. Even though their intentions were considerate and based on compassion she would have been furious at the personal intrusion. All three of them were linked to this spying device and all secretly wanked over the images. 

One Saturday night, Carrie had a night to herself believing that her friends were going away for the weekend. She was all set and spent three hours shaving her body, painting her toenails and fingernails, dressing in her newest basque and stockings, shoes makeup hair, and jewellery. Johnny was now Carrie again and felt divine.

She had about four mirrors on the wall in the bedroom at differing angles so she could peruse herself in all her sexy poses. Her friends had discretely returned to the house and got themselves ready too. They were primed and set to go. 

As Carrie moved sexily around the room, she looked in the mirror and touched herself, posing in all her femme positions. Her friends secretly sneaked into her apartment and crept down the stairs. Dressed in sexy gay clothes, with very tight revealing trousers, they just walked into her bedroom. They made it very obvious that they were all rock hard and that she was on the menu tonight! 

“Don’t worry Carrie, we all adore you and we are going to make love to you tonight. You will have to have all three of us I am afraid and you will have real cock fucking your sissy cunt rather than a plastic dildo. Oh, and by the way, you are going to be swallowing a very large mouthful of cum tonight, including your own. Any questions?” 

Carrie stood there totally flabbergasted, shocked, amazed, horrified yet so unbelievably turned on that she was dumbstruck. 

“Um, eh, what, how, why, I am stuck for words. I mean...” 

“Carrie, don’t worry you, horny sexy angel. In all honesty, you won’t be able to say much as your mouth is going to be very busy. Just be Carrie and enjoy yourself.”

Carrie just stood there trying for a moment to gather her thoughts and feelings. She noticed that all three of them were looking very sexy and aroused.

She considered that, given the chance, she could actually go through with having a sexual relationship with a guy. Now she was facing three guys who were quite clearly going to gang bang her. This wasn’t going to be a nervous fumbling about in the dark situation it was going to be full on.

As her mind was racing with conflicting emotions ranging from disbelief, sexual excitement, fear, incredulity, and confusion, the guys walked towards her. One on either side and her flatmate in front and started to touch her panties.

Three hands groping her, feeling her arse, her hard cock and started to kiss her passionately altogether. Three tongues in her mouth, almost at the same time. She closed her eyes and felt that she was living out a fantasy in a dream. 

She suddenly felt one of the guys, slide his hand inside her panties and down her crack, slowly rubbing his finger around her hole. Carrie was already so excited by all the frantic kissing going on, that she put her hands down and felt for their bulging groins.

Going from one to the other she rubbed them and started to open their trousers. It was almost like she was going into autopilot, acting out the role of a seasoned slut. She had done it in her head countless times. So she just went for it. She was in wonderland. 

Carrie could feel a finger slipping into her sissy hole, and then it felt like another. Her breathing became heavy as she released three hard cocks from their restrictions and stroked passionately. Then without warning, she felt the fingers slide out of her and found herself falling backwards onto the bed owing to a hard push.

The guys quickly undressed, and upon opening her eyes she could see her panties being pulled off. Everything seemed to be running in slow motion as her desperate passion rose.

One of the guys grabbed the bottle of lube she kept by the side of her bed and dripped the olive oil on his pulsating cock. She was so consumed that she didn’t even stop to think of the fact he knew exactly where it was.

He parted her legs, meeting no resistance, positioned himself and gently but firmly slid himself deep inside her. As she gasped two inflamed cocks started to be rubbed around her lips.

With eyes half closed now, she opened her mouth and tasted the first cock’s pre-cum on her tongue, quickly followed by the next. Carrie turned her head slowly to one side, as if in a trance and gorged the hard member. Almost instinctively, she turned and took the other the same way. Her hands moved up and felt for the two sacks swaying by her head and held them sensitively, caressing them as she sucked like a whore.

Carrie could feel her hole being fucked and it felt so much more pleasant than the hard plastic dildos she’d been used to. Even though she was fully engaged in the wonderful sexual ecstasy she was experiencing, she almost felt like a bystander watching a horny porn video. Her passionate desire for this moment to be really happening meant that she just lay there. The one guy pulled out quickly and it was immediately replaced by another fresh cock. 

Then her head was moved to one side. She tasted the oil and gobbled the cock even more desperately than the other. Cock after cock was being forcibly slid inside her relaxing sissy hole and then put straight into her mouth. 

Her own cock was totally rock hard and reached upward on her stomach. She wrapped her hand around it and started to wank. She was not required do anything else but suck and be fucked tonight. She knew this wasn’t going to take long. The momentum and quickening of the pace became overwhelming and she awaited her meal with a delightful hunger. 

The fucking got fast and manic. She opened her mouth wide as two helmets were being forced into it. Her wanking got intense as she vaguely heard the words, 

“We’re going to fill your mouth with our juice, slut. Now, don’t you dare go swallowing too quickly either, bitch? We’ve got a lot of sauce for you!”

Carrie was in a totally unreal place, almost like a dream that she was wanking to. 

“Oh, here it comes,” she heard and then, the sudden surprise of a real life cock cumming into her mouth. The salty load of cum hitting her tongue got bigger, followed by another’s load, and then a third guys offering.

At the same moment that she felt the last spurt of cum shoot out into her wanton mouth, her own orgasm started erupting onto her wet look basque. The pleasure was awesome and she shivered and breathed heavily, whilst licking her mouthful of cum around on her tongue. She swallowed it all down with a grateful groan and then, ignoring the guys, she collected all her cum up with her finger and sucked it off, eye still closed.

Carrie laid there panting with the most satisfied expression on her face you could imagine.  The guys sat beside her, content. They’d done their job, and Carrie had had her first sexual experience. 

She gradually slipped back into reality and became all bashful and shy. 

What had she done! 

“We’ll talk about it tomorrow. You should be on your own to contemplate. When you’ve got your breath back, have another wank. Have fun, Carrie,” her flatmate said and they all got up, got dressed and with a few winks left not saying another word.

She lay there still and realised what had just happened. Her hand slipped down onto her still hard cock and she had one of the best wanks she’d ever experienced. 

Carrie had become a proper sissy now. The guys thought that it was one of the best fucks ever and agreed that they were going to, ‘Do that again, for sure.’  What was ironic was that Carrie was thinking exactly the same thing. Odd that!