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Crossdressing Journey: Tentative Steps - The Next Evening

"The climax of two fun nights in Bath with a fellow bi guy"

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This continues after the exploits of the morning before breakfast.

I spent the day with a heightened level of arousal in anticipation of what might unfold tonight. I didn’t set any expectations, so that I wouldn’t be disappointed, and instead just thought about my lover’s cock. All I knew was that I was expected to wear my black high heeled over-the-knee boots and a short skirt or dress. I was more than happy to satisfy that request. I just spent the day deciding which outfit to wear.

Finally, the end of the work day came and I rushed back to my hotel to get ready. I showered and douched again so I was completely fresh and clean. I also rewaxed my balls and ass to be as smooth as possible. After a little play with my dildo and a bit of lube, whilst thinking about the fun I’d already had, I cleaned my ass again and then set about selecting my outfit.

I went for a black lace bra with matching thong, which did very little to hide my girly cock. I then slipped on a clean pair of black hold-up stockings and pulled on my black over-the-knee boots with a 4.4” heel, as instructed. I strutted around my room feeling sexy and then sat waiting for the time to approach 6:30pm before putting on my a black long sleeve, very short bodycon dress. I sat there and waited with huge excitement, knowing my lover would be there soon.

My room phone rang and I sauntered over in my heels (now getting more used to them) to hear my friend at the end of the line. He was leaving his room and would be there soon. I said I’d leave the door on the latch so that he could come straight in. I put the phone down, checked myself in the mirror, making sure my stocking tops were level and waited by the room window with my back to the door of my room. A few minutes later, I heard my door open and in walked my lover. He slowly walked up behind me and placed his hands on my hips whilst leaning in to kiss my neck. I turned my head to offer my lips and he forced his tongue into my mouth.

‘You look good enough to fuck’, he said and I just thought, ‘Oh, yes please!’. As he turned me to face him and placed both of his hands on my bottom to pull me closer to him, my cock started to grow quickly. I slipped my hand between us and touched his bulge through his tight black jeans, he was definitely growing. He kissed me again with our tongues entwined and his hands straying from my bottom to caress my back and back down to my bottom. He then gently let his hands wander down to the hem of my dress to feel my stockings and then slip his hand up my dress to grope the naked flesh of my bottom. I was in heaven and keen to please him, so I broke away from the kiss and dropped to my knees and unfastened his belt and unzipped his jeans, then pulled them down to his knees. I licked his pre-cum from his helmet that had created a tell-tale damp patch on the fabric of his tight, white briefs, then slipped those down to his knees too. I looked up at him as I now licked the shaft of his lovely cock and kept eye contact as I slipped it into my mouth and bobbed my mouth along the shaft. I used my spare hand to caress and tug his balls and after a while withdrew from his cock and licked his balls before engulfing them with my mouth and sucking whilst gently wanking his cock. He was making all of the right noises so I carried on sucking his balls for a while before releasing them from my mouth so I could return to his cock again. I flicked my tongue on his helmet and rolled his foreskin back with my hand to gently suck. I then gradually picked up speed and took more and more of his length in my mouth. He started thrusting too, but always showed me respect my not trying to make me gag. After a while I could feel his cock pulsing and he pulled away to save his cum for later. I rose to my feet to French kiss him and let him taste his pre-cum on my tongue.

As he regained his composure, he rubbed my bulge through the fabric of my dress and kissed my lips before gently kissing my neck. Again his hands wandered to my bottom and he hitched up the back of my dress to grope my naked cheeks. Then his hand dropped down to my anus which he started to probe with his finger. I started kissing him again and we had our tongues writhing in each others mouth as he probed my anus further, I was getting more lightheaded and weak at the knees as the thoughts of where this could be heading overwhelmed me. He then broke away and removed his jeans, briefs, socks and shoes, leaving him in just his dark blue shirt, and guided me towards the bed. Before seating me on the bed, he had a quick fumble with my hard cock. I was grateful he didn’t wank me too much as I would have cum quickly. As I sat on the bed, he sat next to me and gradually reclined me and slipped his hand between my legs to search for my anus again. I felt extremely vulnerable as he leaned over to kiss me whilst trying to open my sensitive hole and just enjoyed the sensation of being seduced in this way. As he became more and more enthusiastic with my hole, I broke away from him to get some lube and condoms, without being too presumptuous! As I brought them to him with my dress hitched up to reveal my stocking tops and thong, he smiled at me and said, ‘You’re a good girl’, which made me blush.

I was still fully dressed but took the opportunity to remove his shirt to reveal his smooth chest - I’m sure it wasn’t that smooth the previous evening. I asked him if he wanted me to remove my dress and he said, ‘No, I want to fuck you in your outfit’. Wow, that was so sexy.

I sat down on the bed and he reclined me again to lean over me and kiss me, then he hitched up my dress a bit further before removing my thong. My heart started racing in anticipation of what was going to happen and he got hold of the lube and squeezed it on his fingers then went straight to my virgin hole and started massaging the cold gel into it. As he did, he slipped a finger in followed by a second and probed me to open me up. This was incredible and whilst I could hope for this, I certainly didn’t expect it. After a few minutes of kissing me and probing my ass he stood up and took a condom out of the wrapper. Before he could get it on, I leant forward and gave his cock a few sucks to make sure it was fully hard, then watched as he rolled it down the length of his shaft. Wow, this was really going to happen. He grabbed the lube and rubbed some over his sheathed cock and I took the opportunity to rub some more into my hole and waited for him to take me.

I was lying on the bed with my ass close to the edge and my open legs bent with my heels digging into the duvet to steady myself as he approached the bed and got between my legs. He leant over and kissed me passionately, whilst nudging his cock at the entrance to my hole. This was an incredible feeling, which made me raise my boot clad legs in the air and supported them with my hands to make myself as wide open as possible. This gave him clear access to me and he gently eased his cock into my anus. The feelings were mixed with the pain quickly dying down. He rested while I got used to girth and when he felt me pushing back, he knew I was ready to be taken. He started gently and took over holding my legs aloft and he occasionally leant in to kiss me, the feeling of my ass being filled by the cock of this sensuous lover was divine and I became lightheaded again. He started referring to me as ‘sissy’ and his ‘girl’, which I loved. After a while, I felt his pace pick up and I loved the feeling of my cock slapping against me with each thrust, but before long he told me he was getting close to coming. I shouted he could cum on me, so he pulled out, whipped off the condom and shot his cum over my cock, balls and hole.

What a feeling that was, but I instantly wanted his cock back inside me. He kissed me and scooped up some of his cum and offered it to me to lick, which I dutifully did. He handed me a tissue to wipe up the rest (some having soaked into the duvet), and I stood up to remove my dress. He asked me if he had to go, but I told him he was welcome to stay but I did want to go and get a drink and a snack. He agreed to that and suggested we could come back to my room afterwards - yes please!!!

I stripped and I had a quick shower and I returned to the bedroom and put my stockings back on and slipped my thong on too. To allow me to wear my bra on I put on a baggy hoody over my t-shirt, and slipped on my jeans whilst he got dressed. We went to the bar to have a couple of drinks and a sandwich and quietly discussed what had just happened, then when he was recovered, we returned to my room.

On returning to my room, I immediately took off my male clothes, put my boots back on and put on a black tight leather mini skirt and black tight long sleeve top. He came to me and held me again and caressed me. This guy was such a gentle and respectful lover. He kissed me and told me he loved my outfit and proceeded to grope my leather clad ass. I was putty again and before long I was pushed on my back to see him undo his jeans and get his cock out to wank it. Once he was happy with the growth he lifted my legs and sandwiched his cock between my boots and fucked them, which was really horny and he said he’d been thinking about doing that all the time we were in the bar. He then got me to turn over so I was on my front bent over the bed and he got the lube again. He flipped my skirt up my back squirted some lube in my ass and pushed it in with two fingers, then slipped a condom on, lubed himself, slipped my thong to onside and guided his cock to my hole for the second time. He gradually entered me, but this time went straight to fucking me hard. I was groaning with passion and encouraging him by pushing back, he built up his rhythm and called me his ‘sexy slut’, which I took as a compliment. He pounded me and reached round to stroke my cock then he shouted, ‘I’m cumming, I’m cumming’ and he thrust into me as I felt several jerks in the condom. He’d certainly claimed my ass and I felt owned by him. Phew!

He gathered his composure and removed his cock from me and pulled my skirt down. As he went to the bathroom, I stood up and tried to stand up straight but my legs were like jelly after having my ass taken for the second time in two hours. When he came out of the bathroom I was sat on the bed, still fully dressed, with my back against the headboard. He joined me and kissed me, whilst rubbing my cock through the lace thong. I grew harder and he slid down the bed to release my cock from the thong and take me in his mouth, after sucking and wanking me for a few minutes, I gratefully shot my cum in his mouth, only for him to slide back up the bed to kiss me and deposit some in my mouth. That was sexy too. I felt so fulfilled after being fucked twice and being given a blow job.

We chatted for a while and he was stroking my legs and after giving him once last blow job where I swallowed his cum, he left to go back to his room. I took off my top, skirt and boots and kept my stockings and lingerie on. I played with my cock as I drifted off to sleep with a warm tingling sensation in my hole that reminded me that I was no longer a virgin and that I was definitely bisexual and not bicurious. I wish all trips away for work were that productive.

We did swap numbers, but I’ve not contacted as we live far apart. When I arrange to go back Bath next, I’ll message him to see if he can be there again, so I can be his ‘sissy’ and ‘sexy slut’ again.

Thank you for reading. Sorry it is so long. More stories of other experiences to follow if anyone’s interested. xx

Written by Crossdresserfan

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