Making Love in a Dress

At first I didn't make much of my interest in women's clothes. I had tried on clothes belonging to my sisters and tenant, worn their panties to school, gotten erect doing so. I just thought their clothes were nicer than mine, usually hand-me-downs from my two older brothers.
When I had my first secret boyfriend, clothes were not a factor as we did no more than kiss and cuddle in the woods for that summer after school, before he left for university.

Even though I bought a few panties when I got a place of my own at university, had a few more secretive dates and then finally found a man to sleep with, clothing played no part in the proceedings. I was still looking for my preferences and had a girlfriend too, and stole a few of her panties and a pair of stockings too. So I still wasn't associating this clothing preference to my enjoyment of gay sex.

That came the summer after I graduated. I got a good job with a good company (though the starting salary sucked!) in a new town and moved into a tiny bachelor apartment with my few possessions and a big whack of debt. I worked hard to make a mark on my employers and spent a lot of time with a nice female co-worker, getting as far as passionate kissing on my bed but not breaking her will to remain virginal at least until an engagement, which she wanted to hold off on until she too was settled in her career. I cheated on her with an older woman in order to relieve some frustrations (and steal another pair of panties!) but, as things faded with my girlfriend, I started to think about finding another guy.

I wasn't sure exactly what kind of man or what kind of relationship I was after and a couple of trips to gay bars resulted in one unsatisfying blow job and a couple of false starts. I met Gary when I responded to his ad in a local 'what's on' newspaper. Our first meeting at a local bar ended with a handshake and his phone number, which I called a few days later to arrange a lunch meet. I was a little unsure of him as he was a bit older than me, a little pudgy, and was looking for a more committed relationship than he'd inferred in his ad or I had been seeking. My previous man had also been older, a bit older than Gary.

I decided to be honest and say I was not a committed gay, was married to my job, and not ready to be out. But, as we talked, I asked myself if I could love this man. I looked at his face, looked at his lips, and said 'I think so'. Not exactly definitive, but intriguing. So I gave him my number and we chatted more that evening. We agreed to commit to each other for two months and to decide then to either continue with more commitment or to end it.

To celebrate, we had dinner together a few nights later and went back to his place for the night. He had a FABULOUS pad - large, well furnished, all the latest electronics, art, travel souvenirs, a large collection of then-new CDs, and a big fluffy four-poster bed. Before he had told me he was an accountant. He now admitted that he was a partner in the firm, as was his dad. This was the pad he bought after his divorce - brought on when his wife caught him underneath another man. That relationship had ended soon after the marriage was officially over. Now 38, he wanted love. Maybe me? We'd see in a couple of months.

He put off any thought of sex that night but we did kiss properly for the first time. He seemed more enthused after that and we arranged to eat at his place the next evening. After a delicious dinner and washing up, we kissed again. This time there was no stopping us and we went to the bedroom. We had not even discussed our preferred sexual roles so were caught a little unawares. But then I remembered that he had been caught UNDER the other guy so, after nice foreplay, I lifted up his legs and slid in. Yes, this is what he seemed to like. But, after I was done, I found myself on my stomach with his cock driving deep into me. We stayed the night together, closely entwined until I had to make an early departure to get home and change for work. We chatted on the phone that night but, after meeting at my place to see where I lived, we went back to his place for dinner and sex. I did notice how he liked to undress me but to leave my briefs on for as long as possible. We stayed the weekend together, fucked a LOT, and I spent a lot of time in only my briefs.

We met again during the week and I was around at his place straight after work on Friday. I didn't need to bring a change of clothes, he told me. But I hadn't needed them the weekend before either, apart from a change of underwear. I didn't even need those this time as he had bought some for me to wear - delicate little man briefs and one pair of girlie briefs he said he'd bought by accident. Those white cotton briefs, though, seemed to be the one he most wanted me to wear. I realized that if I ever wanted more sex, all I had to do was put on the smallest briefs I could find. He, by the way, wore his dressing gown when not naked.

Another nice weekend, a brief stop over at my place during the week, and we were back together at his place for the weekend. After making love to me with my panties pulled to the side, we were kissing and cuddling between the sheets when he told me how much he liked my body. I thanked him for the compliment. Some might have thought me a little skinny. You wear clothes really well, he added. That was nice to hear as my work suits were very low end compared to his. 'If I buy a few things for you, will you wear them', he asked. I said he didn't have to - I could look after myself, thanks. I didn't want to be indebted to him. I was thinking of clothes just for here, he replied. I had images of bondage-wear or cowboy chaps but he added, rather tentatively, that he thought I would look really nice in lingerie. I, of course, loved that idea but tried not to appear too excited. So I said 'whatever keeps you happy between the sheets.' So I acquiesced. He'd been shopping already, of course, so hopped out of bed and quickly returned with another pair of little cotton-toweled panties and a pair of slightly thick dark blue tights! I put them on and right away he started the slow process of taking them off again. They were still around my knees when he started to fuck me. The best fuck to date - and they were all good. He even finally gave away his age - 35 (to my 23). A couple of other panties came out of the drawer over the remainder of the weekend.

For some reason we didn't get together that week and not until Saturday evening that weekend. We ate dinner out and then went to bed for equally tasty sex. We slept together naked, and I wondered if he was losing interest in the panties. I hoped not. After more delicious sex right after waking, he made breakfast in bed for me and we relaxed for a little while.

'I have something for you' he said. I hoped for panties.He came back with panties, and a bra, and a silky top, and a billowy little skirt, and a pair of tights and garter - something one could almost wear to the office but spiced up with the underwear. He got me to get dressed and then sit on his bare lap while he fondled me under the skirt and, a good hour later, pulled aside my panties and had me sit on him.

I questioned him afterward because he'd told me he considered himself gay yet seemed to me to need me in women's clothing to get most excited. They get nicer clothes, he replied. I used to think I liked women equally to men but I think I just like their clothes! Good enough for me. Any story would have done - I liked dressing up, and the sex was always passionate. He seemed to like us both naked or both normally dressed for kissing and cuddling, but preferred me in women's wear for the best sex.

Over the weeks he kept adding to my wardrobe - a mix of smart casual and casual business wear along with a nice collection of lingerie. I couldn't wear the clothes outdoors as I looked like a guy in drag (as I was!). But I did take mostly his clothes when we went the coast for a week-long holiday and wore the panties under my guy clothes.

All too soon, we came to the two month anniversary and The Decision. I wasn't looking forward to the date as I knew my answer was non-committal. Initially we decided to give each other 'a little more time' but, after another trip away, we sat by the beach and he told me he needed commitment. I said 'sorry, I can't'. He said 'let's go back to our room, make love, and move on'. We made love all night, drove home in the morning, I packed my bags (he let me keep one pair of panties) and that was the end of that.

The funny part was that, maybe a year later, I did some work for his company and he dropped in on a meeting at his office. He smiled when he saw me (he knew I'd be there) and we had a little chat afterward but you'd hardly know we'd had so much delicious sex together. Some time later I found out he had a partner but didn't live with him - even though he was out, he still maintained a facade of being at least single.

I switched between guys and girls for a few years, married a lovely woman and occasionally met men for brief affairs. No briefs involved, though. Sadly.