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.

My heart jumped at the thought. What had I done. It was my idea for the game so I couldn't back out now. I reluctantly agreed before we set up the game.

I was losing terribly, every attempt failed and I was losing lives quickly. How could I have been so bad at this, I used to be great at it. Then I wondered, am I losing on purpose.

I didn't have much time to think about it as the game ended. I had lost again. His grin was massive. He held out his hand for me to take before leading me to his room.

I had never seen his room before, it was the same size and shape as mine. Around the walls were large posters of naked men. All around the room were arses and dicks.

After leading me next to his bed he turned to face me. With one hand behind my back and the other gripping my dick he began kissing me. It didn't take long for me to get hard. Suddenly he dropped down to the ground and took my dick in his mouth.

While stopping to take a breath he took his top off leaving his hairless chest bare. He then continued to suck me off. After a few minutes he stopped and stood up. He took down his skirt revealing his dick. Turns out he too was wearing crotchless pantyhose and no underwear.

He sat down on the bed and spread his legs open. I could see his erect dick fully. It had to have been at least seven inches like mine. I knew what he wanted. I got down on my knees and put his dick into my mouth. I was surprised at the taste, it was rather sweet.

I moved my mouth backwards and forwards sucking as I moved. I moved my hand up and down as I moved.

Finally he stood up helping me to my feet as well. He grabbed hold of my arse as he kissed me. He turned us around so that I was closest to the bed. Together we fell onto it with me on my back. Not sure what came over me, but I wrapped my leg around him.

Letting go he stood up and spun around. Laying over the top of me again he started to suck me off. Above my face his dick was swinging away. I could do only one thing. I moved my head upwards taking it into my mouth again.

Again I moved up and down his shaft as I tasted his dick. Suddenly he lept off of me. He went into his chest of draws and pulled out two things. He took a packet of condoms and some lube.

After putting one on he lubed himself up. Next thing I knew he was sliding himself inside me. I could feel him moving back and forwards as he fucked me. He leaned forward pushing his dick further in me as he started kissing me again. A mixture of pain and pleasure.

Whilst still kissing me he continued to slide back and forth. Suddenly I could feel him beginning to throb. Shortly after he released his cum. Slowly he slide out of me. After taking off the condom throwing it away, he took hold of my dick and began sucking again.

It wasn't long until it was shooting out of me. It was still in his mouth so he sucked up every bit of my cum before licking me clean. When finished he stood up and kissed me while stroking my chest.

"Ive imagined that for so long now." He said.

It had grown late by that point. As part of the deal I climbed into bed with him. He spooned around me. I could feel his dick pushing between me cheeks. Despite this we fell asleep fairly easily. It actually felt strangely comfortable being like this.

The morning sun rose, I could feel two things. One was his arm draped over me with his hand resting on my dick. Which was starting to get hard from the contact. The other was his full erection pushing between my cheeks.

"Hmm, morning gorgeous." He said, his hand now gripping my dick.

"Morning." I replied.

"This certainly feels nice." He said.

He continued to stroke getting me harder and harder. Finally he let it go. He got up and put on a small dressing gown. I could still see his dick sticking out the bottom. I laid there wondering what to do before finally getting up.

My erect cock swayed side to side as I walked out into the living room. As I walked in he eyed me up and down before handing me a cup of tea. As I drank it I could see his cock poking out the bottom of his gown.

After finishing our teas he took the cup from me placing them both on the table. With a single move he pushed me against the wall. His tongue was already down my throat before I knew what was happening.

His hand ran up my legs instantly grabbing my cock along the way. The faster his hand moved the faster his tongue moved as well. I could feel his other hand reaching round grabbing my ass.

I let out a slight moan as I came into his hand. He reached up putting it into his mouth licking his hand clean again.

"Im going to go get dressed." He said.

He left me leaning up against the wall. My mind completely clouded unable to register what had just happened. It was a few minutes before he came out fully dressed. He wore a blue strappy dress, his usual tights and blue high heeled shoes.

He gave me a quick kiss goodbye before leaving for work. Finally I had come round to my senses. I decided to quickly shower before getting dressed for work myself.

The next few weeks continued much the same. After returning home I would strip straight out of my clothes putting on just the tights. We would then sit together watching tv. During which his hand always made its way to my dick. Then before going to sleep we would have sex.

Finally the last day came, part of me was glad but another part was really sad it was nearly over. It was Saturday and neither of us had work. We both layed in bed half asleep. I could feel his cock pushing up against my naked arse. His arm stretched over my waist causing his hand to rub against mine. The movement caused it to get bigger until it was fully erect.

Suddenly I could feel him grip it as he began stroking back and forwards. His other hand on my arse cheek moving slowly towards the hole. He began to finger me as he stroked my cock, slowly at first then growing faster.

Without any warning he flipped me around and climbed on top. His head between my legs and around my shaft while his was directly over my face. Instinctively I put it in my mouth and began sucking. We both moved faster till we felt that expected feeling. We came at the same time. I could feel it dripping down my throat.

"Well, morning gorgeous." He said as he climbed off.

"Morning." I replied.

"Last day today. Shame really, I got to go out, would have been nice to stay at home with you." He said.

"Well there's always when you come back." I replied.

Why did I say that, I was free and clear. Now ive just given permission for later.

"Im afraid not, but I'll bring a nice surprise home for you." He said as he started getting his clothes from the wardrobe.

He put on a pair of yellow panties over his tights and a yellow dress. He gave me a quick kiss before heading straight out. I wasted no time in getting up and getting washed.

The rest of the day I spent just chilling out. I watched a film before playing some console games. For the whole day Henry was away. Despite this I kept my word. I remained in just the tights and nothing else. My cock dangling from the hole.

It wasn't until late that Henry returned. I had just finished clearing up after dinner when he walked through. I went into the hall way to greet him only to find he wasn't alone. Standing next to him now staring at my cock was a woman only a couple years younger than him.

"Jim I'd like you to meet Tina. Tina's my sister and shes wanted to meet you for a while." Henry said.

"Hi, its really nice to meet you." She said as her smile got bigger.

I found myself twitching as I felt her eyes gazing at me. I was lost for words. There was this beautiful woman standing in front of me while I was nearly naked but with everything on display.

Tina was a slender girl with decent sized breasts. Her soft brown hair was cut at her shoulders. She stood there wearing a tight blue dress that showed her beautiful figure perfectly.

"Hi." I finally managed to say.

Henry showed her into the living room before finally coming back to me.

"Whats going on?" I asked quietly.

"Ive felt a bit bad about taking advantage of you and my sister genuinely wanted to meet you. I thought you'd make a good match. Plus now you dont have to be nervous with her, shes already seen everything." He replied.

"And the fact im wearing these." I said.

"Oh she knows all about the bet. Look you're officially off the hook now. You can take them off and get dressed if you want." Henry replied.

"Oh please dont." Tina piped up.

"I kind of like what I see." She said giving me a wink.