Written by Matty

22 Feb 2010

After university I got a job working in Central London. I found a room in a shared flat in Clapham through the Evening Standard. It was small, but cheap, which was the most important thing. There were two other young guys in the flat and the landlord, a guy of around fifty, who was openly gay. I was very naïve and found the openly gay nature of the landlord a bit scary, I guess, but the other two guys were straight and they didn’t seemed to mind him.

One of the other lads, Steve, had a girlfriend and they spent half the time in the flat and the other half at her place. After I’d been there a month or so I needed to get something from his room, I think it was a CD I’d lent him that I wanted back. He was out, but I put my head around the door to see if I could see it lying about. The room was a complete mess and there was no sign of my CD, however there were a lot of her clothes lying around. I picked up a pair of her knickers which were very silky and sexy. There was nobody else around so I borrowed the knickers and rubbed them all over my body when I played with myself in bed that night. In the weeks that followed, whenever Steve was staying at her place, I would do the same.

About a month later I had a day off sick, having woken up with an awful hangover. Since I was alone in the house, I wandered into Steve’s room to borrow some knickers. Having more time to explore I looked in his wardrobe and found more of her clothes, including a suspender belt and some stockings. For some reason I decided to try the stockings on. They felt great and some half an hour later I was in a very excited state wearing stockings and suspenders, knickers, a bra, a skirt and a blouse. I have always been fairly slim and everything fitted, although the knickers and suspender belt were a bit tight and I couldn’t do up the skirt properly.

I stood admiring myself in the mirror when the door opened and Mike, the landlord, stood in the doorway. I was horrified – he just stood for a few moments and stared. Then he said – I didn’t realise you were a little cocksucker! I told him I wasn’t and tried to get past him to go back to my room, but he stood his ground in the doorway. He said - I think you are, assuming you don’t want the others to know what you get up to when they’re out. I didn’t know what to say.

He kicked off his shoes and took off his jeans and pants. He told me to kneel down. I did as instructed. He started playing with himself and quickly developed an erection. He was just a matter of inches from my face. Then he asked me what I was waiting for. Tentatively I reached forward and took his cock in my hand. It was hot and very hard. He told me to put it in my mouth. I did as I was told and started to suck him. I realised that I was going to have to increase the pace if I was going to get it over with. I started to go faster, but I was fairly clumsy and he slowed me down. He kept telling me how he wanted it and I just obeyed his instructions. After twenty minutes or so he told me he was going to cum and told me I was to swallow every drop. I did as I was told. Afterwards he said thanks and picked up his jeans and left the room.

I quickly took off the clothes and went back to my own room. I got dressed properly and left the flat, feeling very humiliated. I walked around Clapham for a while until I calmed down.

When I returned nothing was said. He didn’t tell the others and everything got back to normal. After a week or so I started borrowing the knickers again when Steve was at her place for the night. The weird thing was my fantasies had changed now and sucking cocks began to feature in them.

A few weeks later both the other lads went home to their respective parents for the weekend leaving me alone in the flat with Mike. I was out most of the day and got back about six in the evening. Mike was sitting in the lounge with another guy. He called me in and introduced me. his name was James. He was mid fifties, well built and had very close cropped grey hair. Mike said he’d told James how nice I looked in my girly clothes and he’d like to see for himself. I was mortified! But Mike said “off you go then” – clearly an instruction. I went to my room. For a few moments I thought about packing a bag and going home. But home was a long way away and I had work on Monday morning. I went into Steve’s room. For once it was tidy and I hoped for a moment that there was nothing for me to wear. But when I looked in the wardrobe my heart sank – ample supplies were available. I put on stockings, suspenders, knickers and a bra, topped off with a skirt and blouse. I tentatively walked into the lounge.

Immediately they began teasing me, telling me how pretty I was and so on. They got me to do a twirl and walk around the room. Then Mike told James I didn’t do a bad blow job if he fancied it. James asked me if that was true. Mike replied of course it was, asking me to confirm. I nodded. James stood up and unbuttoned his trousers, letting them fall to the ground. Then he sat back down again. I stood motionless for a few moments, then gave in to the inevitable and knelt at James’s feet. He didn’t have an erection, so I had to put his soft dick into my mouth. As I sucked I felt it harden and pretty soon I was performing as I had for Mike a couple of weeks previously. I tried to remember to do it as Mike had instructed me, oddly wanting to please this guy. Out of the corner of my eye I noticed that Mike was now openly wanking himself as he watched.

After about five minutes or so James said that I should give Mike a go. I moved across and did as he suggested. As I sucked Mike I felt James caressing me through the silky women’s clothes and telling me how sexy I was. I was surprised to find this all a tremendous turn-on. Then James asked me if I knew what Poppers were. I didn’t. He told me to take a sniff and I’d find it very relaxing and he put a small bottle under my nose. I inhaled and almost immediately began to feel light headed. I stopped sucking Mike, but he reached down and put himself back in my mouth. James asked if I liked the Poppers and I moaned something vaguely positive. Then the bottle was back under my nose and I was inhaling again. His hands were still stroking me all over, concentrating mainly on my bum. Then I felt him remove the knickers and then I felt something cold on my back. I started but he said it was ok, it was just massage oil.

Gradually he began to massage my lower back and my bum. Bit by bit his hand went lower and before I had time to think he was massaging the oil into my bum. I felt a finger enter me and a few moments later a second. It felt very tight and I was feeling unsure. Then the bottle was under my nose again and I felt even more light headed. Around that time I think I stopped sucking Mike. Then James removed his fingers and moments later I felt the tip of his cock enter me. As he pushed it hurt and I tried to pull away. Mike held me and told me it was ok and James gently moved in and out, opening me up further and further. I was in a lot of pain and just as I thought I could take no more I felt his body against mine and realised he was completely inside me. He began gently to build up a rhythm and Mike gently pushed himself back into my mouth. I still felt very woozy and I really just let it happen. I don’t know how long it went on for but it must have been twenty minutes or so. Then all of a sudden Mike was spurting jets of cum into my mouth and moments later James was doing the same into my bum. And a minute or so later it was all over. James went to the bathroom to clean up and Mike went off to his bedroom. I picked up the discarded knickers and went back to my room, sore and bewildered. I lay on my bed thinking about what had happened and Mike brought me a cup of coffee and asked if I was ok.

I lay on the bed, still in Steve’s girlfriends clothes for hours, just staring at the ceiling. Then about eleven o’clock the door opened and James came in the room. He picked me off the bed, took off the skirt and blouse and helped me under the covers. I assumed he was worried about me and was checking I was ok. But then he turned out the light, undressed and got in beside me. He fucked me twice more before we went to sleep. I awoke at about seven feeling very disorientated, Gradually I remembered what happened. I was still wearing stockings and suspenders, although the knickers and bra had disappeared somewhere in the events of the night before. James was still sleeping. And at that moment the most surprising thing of the whole event happened. Without being asked I went down on James and he gradually woke up from his sleep to find me sucking on his cock. He fucked me once more before he left that morning and I gave Mike another blow job that afternoon, before the others returned home.

During the months that followed there were one or two other incidents with Mike and one or two other friends of his, though I never saw James again. Then I started seeing a girl from work and moved in with her and never saw Mike again. I have now been married over twenty years and have never had any similar encounters but I still think back to those few months as Mike and his friends’ plaything with reasonably fond memories.