Hi.
Part two of my story about my first time with a man.
For those who didn't read my first post, I'm a TV. I have been dressing since I was a young boy, in my mothers bras and knickers, then a neighbour's daughters little bra and panties, before progressing to my (very sexy!) aunt's things. I now dress as often as I cam, and am dressed today. I have a black lace 36B bra, pushing my little breasts together to give me a lovely cleavage, matching panties, barely-black sheer lace-top hold up's and 5" heels. As I type, I can see myself in the mirror, stockinged legs tucked under my chair, and feeling very sexy. I have a thick dildo inside my arse, and as I move on the chair, it pushes deeper inside me, as my cock gets hard.
Anyway, back to my story, and my first time with my best friend, Steve.
I have known Steve for over twenty years, from when we met at work as teenagers just out of school. We have always been close, even when he got married 10 years ago, and after he and his wife divorced, we became even closer. That said, neither of us ever believed (or perhaps would admit!)that we were anything other than best mates. However, each time we dropped one or other off at home, we would chat, and many times it I felt that the most natural thing in the world would have been to lean towards each other, and kiss longingly and passionately.
It has been three years since the divorce, and Steve has not settled down with a girlfriend. As we have got older, I have become more and more attracted to him, and wanted more and more to tell him the two secrets he didn't know about me - one, that I really fancied him, and two, that I loved to drees in womens's undies and clothing. You can imagine my excitement when a month ago, he told me that he had been to some gay clubs, although nothing had developed. I immediately felt my cock getting hard, and rralised I wanted to be his first male lover. However, I worried that ours was just a friendship and he wouldn't fancy me, or he would be turned off by my crossdressing. Best to know one way or the other, so I decided to test the water...
Over the Easter weekend, I was meeting Steve for a drink on the Saturday night, so before going out, I had a long bath, shaving my body all over (except for a small triangle of pubic hair), and moisturising my legs. I put on a pair of really sexy panties in black lace, and, worrying that a bra would be too noticeable, put on a black satin camisole. I then put on a pair of lace-top hold-ups, in sheer back, that looked gorgeous against my newly-shaved legs. I then put on jeans, jumper and trainers, checking that my stockinged ankles didn't show. Almost shaking with anticipation, I then put my favourite black ra-ra skirt into a holdall, along with a black, low-cut shoestring top, black high heels, and some make-up. I put the holdall in the car boot.
I drove to the pub, where Steve and two mutual friends, were already at a table. I was so excited, I was almost trembling, and felt sure someone would notice something. Inside my panties, my cock was hard, and I could feel the tip getting more and more moist. After what seemed an eternity, Steve got up to go the gents, and about 30 seconds later, I followed him. I was in luck - Steve was the only one at the urinals so I was able to stand next to him. We peed and had the usual small talk, but as we were finishing I took the plunge, and still holding my cock, looked directly in Steve's eyes, and then slowly ran my eyes down his body, and looked at his cock. I looked back up to his eyes, saw him smiling, so I turned my body slowly towards him. His eyes wandered down to my by-now stiff cock. I saw his cock immediately start to stiffen. Not a word passed between us, but the tension in the air was unbearable. I then pulled the flies of my jeans wide open, so that there was no hiding my black lace panties. Imagine my joy (and horniness!), when Steve leant across and first caressed my cock, before then gently rubbing the lace of my panties. I whispered "Later", but just to get him in the mood, I dropped my jeans just enough to show the lacy tops of my stockings, and then pulled up my jumper to reveal my camisole. As Steve took his hand up and away from my cock, he gently squeezed one of my nipples before I lowered my jumper. We both turned back to the urinals, and somehow tucked our stiff cocks back in our jeans.
We went back to the table, and I was able to sit next to Steve, taking great pleasure in rubbing my leg against him, pretending he could feel the top of my stocking. Finally, it was time to go - I told the others I would give Steve a lift, and after they had left, I asked Steve to give me 10 minutes start. I walked out to my car, which I had deliberately left at the far end of the pub car park, whick by now was quite dark. I took the holdall out of the boot, and got into the car. Almost panting with excitement, I took off my trainers, jeans, jumper and camisole, replacing them with the push-up bra, the low-cut top, the ra-ra skirt and the high heels. Taking a chance with the car's reading light, I quickly applied lipstick, eyeliner and blusher, and mussed my hair into a feminine style. Smoothing my new clothes down, I sat in the car, and waited for my heartbeat to slow down.
After two or three minutes, Steve came out of the pub, and spotting my car, walked across the car park and opened the passenger door. As the door opened,the internal light came on again, and Steve saw what I was wearing. The expression on his face and the bulge in the front of his jeans told me that I had had the desired effect. As soon as the light went off, he leant across and kissed me, first on the lips, but then fiercely pushing his tongue into my mouth. At the same time, his hand went under my skirt, and felt my cock through my panties - I thought I might come then and there. After what seemed like minutes, our faces moved apart, and he was able to take a long, hard look at me. I could see his eyes taking in my little boobs, my cleavage, and finally my legs, which the sheer stockings and high heels made look very long and slim. Finally, he spoke - telling me how he had fancied me for ages, but had been too scared to say anything, and how great I looked. I asked if he would like to go somewhere quiet, and he answered yes immediately, careesing my thighs as we spoke. I slipped off my heels as I was worried about driving in them, and we slowly pulled out of the car park, heading for a largely-disused industrial estate about 10 minutes away. As we drove, Steve undid his jeans and took out his lovely big hard cock - slowly wanking himself with his left hand, while rubbing the crotch of my panties with his right hand. After taking a couple of side roads, we finally arrived at the industrial estate's big car park, which, as I'd hoped, was dark and deserted. We parked, and after putting my shoes back on, I got out of the car, and walked slowly round to the passenger side, all the time lit by the car's headlamps. I opened the back passenger door, and waited for Steve to join me.
More to follow.....
