First Time Crossdressing with a mate part 1

This is a work of fiction, though someday I hope to make it a reality.


It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I dressed up like a slut for the first time, I couldn't stop thinking about meeting another crossdresser for some horny mutual fun. I had been faithful to my girlfriend, but after that halloween party where she dressed me like a slut, I realized that there was a whole side of me yet to explore that lay untapped. My partner knew I was bisexual, and was into me crossdressing occasionaly when we had sex, so I felt comfortable telling her about my secret fantasy.

I explained that there was a fantasy that I'd like to live out, and she was totally fine with it. She knows I'm not going to leave her for anyone, so she feels like she can trust me and doesn't need to control me which I am extremely thankful for. I give her the same trust and freedom.

"Go for it!" she said. "I'm away next week and you have the house all to yourself with all my sexy lingerie...". I was relieved that she was understanding and joyful that she was so encouraging.

So a few days before she left, I put an ad up on Craigslist. I explained my fantasy in great detail, attached a few discreet pics, and clicked 'post', hoping for the best. I explained that I was an attached bi male, who recently got into crossdressing, and was looking for another young, inexperienced but open minded fit guy to explore our feminine side together. I was mainly looking for body contact, mutual wanking and sucking, but open to where things went from there depending on the chemistry.

Before long I started getting replies, most of them timewasters. But 3 days after my posting I got the reply which gave me butterflies in my stomach. It was from a really sexy guy with a great body, unbelievable legs and an ass to die for. He was half Thai half Spanish, with naturally long black hair and green eyes. His extremely fit body was peppered with tattoos and piercings, and was naturally quite smooth, though you could tell he hadn't shaved or anything. In my favourite pic he sent me, he was wearing fishnet stockings with a suspender belt, and a sexy nightie that hugged his figure very well. Poking through his crotchless panties was a gorgeous 6.5 inch cock that was neither too thick nor too thin. It stood erect and straight, with no kinks or bends. My mouth started watering instantly as I saw the pictures, each one hotter and sexier than the next.

On top of that the message he wrote me was clear, coherent, friendly and made my cock rock hard just reading it. He said he was in the same situation- attached, bi, recently got into CD and wanted to dress up with another CD for the first time. He said that although he wasn't smooth, he was willing to become so if I would too. He also said he was into porn, 420 and more, and was looking for a slow, relaxed, all night meet where we could really take our time. Everything was perfect, and I could feel it was genuine. He left a mobile number, which I called.

When he answered, he was friendly and polite. We arranged a day to meet and I asked him to please not masturbate for at least 3 days before our meeting. He liked the sound of that, and we decided to book a hotel and split the costs, as it was the first time we were meeting and neither one of us felt 100% sure about hosting at our places. We booked it for the coming Friday evening through to saturday evening. Before the date arrived, I made sure to get some wigs and high heels, which were the two things I was missing before.

Friday arrived, and we agreed to meet in the hotel bar at 9 for a drink before going upstairs. Both of us would be in our normal mens clothing at this time so as to be discreet. When I walked into the bar I instantly recognised him from his long hair, which was braided into 2 large piggy tails. He wore a tank top that showed off his toned frame very well, and he looked hot as fuck. I was secretly jealous of how his face seemed to suit being male or female both very well. He was a natural either way.

We hit it off and it was obvious there was great chemistry between us. We laughed and joked and after the first round of drinks, he suggested we move up to the room. By this time I was feeling totally comfortable with him, and couldn't wait to get the night started.

As we arrived into the room, both of us were impressed at the size of the bed, and the bathtub. Wasting little time, he asked me to describe to him in detail what I wanted to do tonight in an ideal situation. I told him I would love us to shower together, shave each other completely, then help each other dress up in our sexiest outfit. From there we would roll a joint, throw some shemale porn in the big screen, and start massaging each others bodies with oil. Once we were all nice and slippery, I wanted to get into a 69 and stay there for as long as possible. I asked what he thought of this and he said it sounded absolutely perfect.

So we got into the shower together, and began by slowly and sensually lathering each others bodies up with soap. Once we were all lathered up, he asked me to shave his body, but to be extremely careful. I started on his back, where there was hardly any hair whatsoever, and then turned him round and did his chest and belly. From there I did both of his legs, and then his butt crack. I went extremely slowly and gently, and his cock was growing considerably as I made it closer and closer to his balls. I shaved all the hair from his balls and cock, and then I was done. There wasn't another hair left on his body, apart from his head.

I then got into position so that he could shave me, and he did so with utmost care and attention. By the end of it, my skin was so silky and smooth I couldn't believe it. We stepped out of the shower, and went out back to the bedroom, where we had our outfits all laid out and ready. We both went for stockings and suspenders, mine were opaque and his were fishnet. To that we both added matching bras and crotchless g strings which allowed our cocks to spill out freely. We helped each other into our clothes, did each others make up, and finally put on our wigs.

The transformation was incredible. Both of us were already a bit on the feminine side, but neither of us had ever shaved our bodies completely before so just the feeling of that was enough to get our cocks rock hard as we put on our outfits. He was now a she and she looked even hotter than the pic I had been wanking to for the last week! She commented on my gorgeous figure and yummy looking cock as well.

I then announced I was going to roll a joint, and asked if she could pull up some nice shemale oral porn to get us started. I was just finishing off the joint when the lights dimmed, and the screen came on. She came over to where I was on the bed and sat next to me. We smoked the spliff there on the bed together, both of us looking at the screen and getting harder by the second. After the last toke, I moved closer to her and placed my hand cupped around her balls. She let out a little moan, and her cock twitched. I took my hand to my face, spat into my palm, and then rubbed my saliva on her cock, stroking it ever so gently. She wasted no time in reciprocating, and my cock swelled in anticipation.

"I want to taste your cock so bad" I said to her.

"Let's do that 69 then!" she replied, and we made ourselves comfortable on the bed.

Just having her juicy cock right in front of my face was so hot, I instinctively spat on it an grabbed it with my hand, guiding it slowly into my mouth. I slowly ran my tongue up and down her shaft, and heard her moan loudly. I could feel the wamth of her mouth covering my cock too and I groaned with delight. The feeling of her cock in my mouth was divine, and having her slobbering over my cock at the same time was driving me wild.

I told her that we should be careful, as we don't want to come too soon. I suggest we spank each others bums when we feel we are getting close to coming, so that we stop for a second and let the wave subside. I wanted her come in my mouth alright, but not until I'd edged it for a good couple of hours first... She looked at me with a dirty smile and winked, and I almost melted right there. She was so hot as a girl, I just wanted the moment to last forever.

Struggling somewhat to keep my balls from exploding, I took my time to tease, nibble, stroke, lick, slap and spit all over her cock. I loved the feeling of grabbing her cock by the base, and slapping it against my tongue and cheeks. Every time I did that I could hear her saying "Fuck yea baby that is so hot". She was deep throating me now, but extremely slowly and sensually, stopping to gently slap my ass and ballsack every so often. Her cock was drenching wet with my spit now, it was running all down her balls and into her crack. I took my time licking and sucking her balls, taking both of them into my mouth at the same time, while wanking and lightly slapping her cock.

We continued to worship each others cocks for what seemed like forever, neither one of us in any hurry to stop, both of us relishing every lick, suck and slap. Every now and again the electricity would build in our nut sacks and we would slap the other persons ass to signal that we needed to slow down. In this way we edged each other until our balls were literally aching and sore.

"I have to be honest mate, I don't want to stop but I really need to pee" she said, while simultaneously smearing my cock all over her cheeks. "That's fine, why don't we have a little breather, roll another joint, and start again in a minute?" I suggested. She took my shaft all the way down her throat, bobbed her head lightly from side to side, and gagged on my cock. She seemed reluctant to want to give it up, so I pulled it out of her mouth and slapped it against her face gently "Be patient now, we have plenty of time.." I reminded her.

She smiled, and went over to the bathroom. Her cock was so hard it took a while for her to be able to pee, and by the time she was out I had the spliff lit. We toked it together, staring into each others eyes, grinning like mad. This was heaven!

It wasn't long before the spliff was done, and I asked her if we could take turns sucking each other for a bit. She seemed happy with that, and asked if she could start. I lay down on the bed, spread my legs and began stroking my cock until it was fully erect again. She got on her knees and began to tease my cock with her tongue, licking it up and down and in circular motions. Soon she was doing the slow motion deep throating which felt so damn good.

"I love it when you take my cock deep in your throat, it's so fucking hot!"

"Your cock feels so good inside my throat baby' she mumbled- I could barely understand her as she was still mostly gagging on my cock.

"Spit on it" I said to her.

"You love it all nice and wet, don't you baby?" she said seductively, while looking me straight in the eyes and spitting all over my meat.

"I love feeling my cock soaking in your saliva you cute little slut! Oh god yeah you're such a good little slut, your throat feels so good!"

"I love being your little slut baby!"

"I want you to sit on my chest and gently feed me your cock. I want you to slap my face and tongue with your cock until I beg you to slide it in my throat!" I said to her.

She moaned, took my cock out of her mouth and looked at me with fire in her eyes. "You want me to feed you some cock honey?"

"Yeah baby I want you to feed it to me softly, gently. I want to feel your cock rubbing all over my face, all slippery and wet".

She got up from her knees and climbed onto my chest. Her but cheeks were still oily and they slipped and slided against my chest so beautifully.

"Is this want you want baby?" she asked, as she placed her cock an inch away from my mouth.

"Please give it to me! Feed me your gorgeous girly cock!" I begged, opening my mouth wide. She slowly slid her length down my throat until I was balls deep on her 6.5 inch cock. I managed to control the gag reflex and she left her cock fully in my throat for a good while before slowly beginning to slide it back out. "Mmmmmmm" I groaned, "Your cock is so tasty". I spit on my fingers and brought them round to her ass, sliding my wet fingers up and down her smooth crack, applying just a tad bit of pressure as I crossed over her tight hole.

"Can I play with your hole while you feed me your cock?" I asked her. Her head was tilted back and she was moaning very loud now.

"Fuck yeah baby tease my tight little virgin asshole while you gag on my cock" she demanded!

I kept pushing down on her little hole, all nice and wet, but not hard enough so that my finger would actually penetrate through. She was actually jerking her cock off into my mouth now, while I kept teasing her hole.

"Do you want to come in my mouth you sexy bitch?" I asked her.

"Fuck yeah baby I want to squirt in your mouth".

Her bumhole was well and truly relaxed now from all the teasing, so I slowly slipped a finger in while continuing to gag on her throbbing cock. She let out a high pitched squeal that was incredibly seductive. I felt my balls tightening just as she said "I wanna taste your cum too honey".

We repositioned ourselves into the 69 position, both sucking each other hard and fast now, wanking each others cocks into our mouths.

"Here is comes baby, don't stop. Oh fuck yeah keep going, keep wanking my cock into your mouth" she begged me. I could feel she was getting close and it was turning me on incredibly. I started wanking her cock into my mouth as fast as I could, realizing I was about to come as well. She screamed "Oh Gooooooooooood" as she pumped squirt after squirt of hot salty cum directly into my mouth. There was so much of it I had to gulp twice just to clear my throat, and her cock kept squirting for ages. As I felt the first shot hit the back of my throat I couldn't hold on anymore and moaned extremely loudly. My mouth was full of cock and cum otherwise I would have screamed!

She wanked my cock directly into her mouth and I came with her lips 3/4 of the way down my shaft. She gagged involuntarily, slurped and swallowed the first few squirts, then let the rest of it continue collecting in her mouth but without swallowing it. Eventually when my cock stopped squirting she was left with a pool of cum in her mouth despite having gobbled up most of it already.

She spat some of it back out onto my cock, further drenching it. It felt so nice to have a pool of my own cum spat back on to my cock! Before I could think about it, she then reached in and gave me a sloppy wet kiss, making sure I got a good taste of my own seed.

It was so hot, kissing her with my cum filling out mouths.

"That was fucking incredible!" she exclaimed.

"I can't remember the last time I came so hard" I replied.

"Well, the night is young, shall we grab another drink, have a little break and then see what happens?"

"As long as whatever happens involves us blowing each other".

She smiled and looked at me as if to say well isn't that why we came here?

To be continued...


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Posted by obm_cd
7 months ago    Views: 2,376
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6 months ago
omg that was sooo hot. mybiggest fantasy is being with another sexy boigurl in panties and playing
7 months ago
Hope part 2 is on the way
7 months ago
Great story! Sound very similar to one of my favorite fantasies!
Please continue with part two when you can!
7 months ago
I hope you continue this story I'm so hot and I came already I want to cum again