A gay sex story: The New Roommate
It was six months since that holiday. Not much had changed during that time, our time together had made me and Eric better friends. We never slept together again, but sometimes we would just hang out with either little or nothing on.
I had also got to know a few of his friends as well. The main one who hung with us was Henry. He was a tall slender man with black hair and blue eyes. That however wasn’t the most interesting thing about him though. He was a crossdresser. He could often be found wearing either a dress or skirt and always with tights.
Im not sure exactly what it was but there was something about him. Something that felt strange. Often I would catch him looking at me. I just ignored it though, he was a friendly enough bloke and we got on well.
It was the following month when things began to change. Things had greatly improved for me at work causing them to promote me. Downside was the promotion was in London. I couldn’t commute every day and I couldn’t afford a place by myself.
“Henry’s got a two bedroom place, he’s been looking for a new roommate for a while now.” Eric said.
“Yeah I guess that could work, would you be able to ask him about it, I haven’t got his number.” I replied.
“Sure, tell you what, I’ll give him your number so he can ring you about it.” Eric said.
“Yeah that’ll be great.” I said.
“You wont mind living with him though, you know with the way he dresses, plus he’s gay like me?” Eric asked.
“We’ll just be living together, its not like we’ll be getting married.” I replied.
And so Eric set things up for us. After talking with Henry and getting the details I packed up all my belongings and moved to London. The move was easy, Henry helped out a lot helping me layout my room perfectly.
He showed me around the house, it was a good size. The living even had a games console which he said im more than welcome to use. After looking through his games I saw one that was a favourite of mine.
“Star Wars Battlefront 4, I haven’t played this in ages.” I said.
“One of my favourites, tell you what, we can play it together if you want, I have two controllers.” Henry said.
“Yeah that would be awesome.” I replied.
And so the first two months went by. Every Saturday we’d play Battlefront together in the living room. When playing against each other we even started to make forfeits for losing. Often things like washing up or bin duty.
After playing we’d then watch a film together, turns out he had a similar taste in films as me. Things were running smoothly. Things however were about to change. It was over the next couple of weeks that the forfeits got a bit more elaborate.
One week he had me run outside in just my boxers, the next he had to clean the whole living room on his hands and knees. This of course was just the beginning.
“Okay, its all setup, you ready?” I asked.
“Yeah im coming.” He replied.
He came in wearing a short purple skirt and purple top. His legs glistened under his tights. He sat down causing his skirt to rise up slightly and grabbed the controller.
“So whats the stakes today?” He asked.
“So, if I win, you have to send a dick pick to someone you fancy.” I said.
“Okay, if I win, when we watch the film tonight, you wear nothing but your boxers, we cuddle up and I have my hand down inside your boxers the entire time.” He replied.
I thought about it for a little while before agreeing. I thought to myself, im going to beat him today. We set up the match and begun the game. To begin with I was beating him easily, then it all turned around on me. He started to get ahead of me. Then the match ended. He had won.
“Yes ive won, well im definitely going to have a good night tonight.” He said.
I was left speechless as he packed away the console. He gave me a wink as he walked away. I remained there in shock unsure of what to do. Finally I came to my senses and returned to my room.
A couple hours later it was time for the movie. I stripped down to just my boxers before walking into the living room. Henry was already there waiting for me.
“Ive put the film in, we’re all set.” He said.
I sat down next to him where he instantly cuddled up to me. After hitting play he put his hand down my boxers and gripped my dick. During the course of the film he would softly stroke it or play with the tip. Despite my best efforts it grew hard.
I could tell he was enjoying it very much. I was surprised that I was enjoying it as well. It felt nice having someone touch me again, even if it was him.
When the film ended he slowly removed his hand stroking against my dick as he moved. He gave me a kiss on the cheek before walking off to his room.
The rest of the week was fairly boring after that. Both of us carried on with work and social life. After the week ended Saturday arrived again. Again the console was set up.
“So, what today then?” He asked.
“If I win, then you’ll go to the man you fancy and kiss him.” I said.
“Easy, if I win then you will wear nothing but these in the house for a whole month.” He said holding up a pair of crotchless pantyhose.
“Nothing else, not even underwear?” I asked.
He shook his head. Very clever, hed have me in tights but also have my dick swinging for a month.
“Okay then, you’ll not win this time.” I said.
The game started, originally I did everything I could to win. Then I began to think, I remembered how it felt when he touched me. I saw how the tights looked on him. A part of me wanted to try it, part of me wanted him to see me naked. I began to lose.
It was partially on purpose but also through his skill. Again he won. He did a little celebration before holding up the tights.
“You might as well change now.” He said.
I conceded. I took them from him and stood up. Bit by bit I took my clothes off until only my boxers remained. Bending down as I moved they too came off leaving my dick to swing free. He stared at it like a hungry beast.
Sitting back down I pulled on the tights allowing my dick to swing free through the hole. I could see his crotch growing as he looked at me.
“Very nice.” He said.
As requested I walked around wearing nothing else, every time he found some excuse to watch me. When the evening came I had gotten used to being dressed like it. Again we sat down and watched a film. Without asking though he cuddled up to me and instantly held my dick. I should have protested, but I didn’t.
The entire night he stroked me, played with the tip or played with my balls. When the film ended again he kissed me before walking away.
The next day I awoke to find him in the living room, normally he would be at work, but there he was.
“Dont you normally work today?” I asked.
Again he looked straight at me free swinging dick.
“Booked the week off.” He replied.
I thought popped into my head.
“Fancy another game then, give me another chance?” I asked.
“Okay then, so whats the stakes?” He asked in response.
“If I win, I get to put my normal clothes back on.” I said.
He sat there and thought for a bit before smiling.
“If I win, you have to be my boyfriend for a month. That means kissing me, sleeping with me in my room. Having sex, the lot, plus you stay dressed like that.” He said.