My Cuck Roommate free porn video

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Several years ago I split with my long time GF, Miki. It was a friendly break up so I agreed to be the one to move out of our place. My long time friend Chris happened to be looking for a roommate at the same time. He had been going through a divorce and it had finally gone through. So I ended up taking the room. This was before I met Miku so this is a recounting of some of the time between them.

Now the twist of this was that he was Miki's ex. If you've read my other stories you may have read how I met her. Chris was the married guy she went out with for a few months. We also had a threesome with him later on after I had turned Miki into a slut. So he was very aware of my kinky side.

Chris was a horn dog himself, very good at sniffing out horny Japanese women. Just a normal guy; short, a little pudgy, receded hairline but friendly and attentive. Not that it matters but also a little dick. Not overly so but it was a factor that came into play later.

The first few months as roommates were nothing special. We worked different schedules and ended up passing each other often and didn't spend so much time hanging out. We also spent a lot of time in our own bedrooms with our women friends. But as time went on we did get to hang out a little, often when bringing home a new fuck buddy. One time that matters to the story was when I met Mako. She was a single mother with a teenage son that was about to go to college. She was super friendly and I could tell really liked Chris. We chatted for a bit and she also added me to her friend list. And that was that. Fast forward a month or two and I get a message from her asking me if I can chat online. We start talking and I find out she's upset because she can't get Chris to settle down. I ask her what did she expect, he's recently divorced and had a history of cheating before. She says the usual "I know but I hoped I would be different." She tells me she had basically threatened him that she would fuck some other guys too. It had back fired as he had told her to go ahead.
Now she didn't know what to do. She didn't really want to fuck anyone else. I told her that she had screwed herself and the only way she was going to get any respect back, from him and herself, was to go through with it.

So later on that week I get another message from her telling me she met some guy online from the air force base and he was coming to her work place to pick her up. She was having second thoughts and didn't know what to do. I asked her if he was already on his way and she says yes. In told her it would be a dick move to back out now but if she was just nervous. But if she felt she didn't want to do it she should leave. I got no response from that day.

Now a couple of days later I message her asking if she's alright and ask about how things went. Turns out the guy had shown up, and since she worked late it was just the two of them there. She fucked him right in her office. I asked her how it was, she said good and that he had a big dick. She said she came a couple of times. I asked her if she would meet the guy again and she said no. She still wanted to be with Chris. I asked her if she had told Chris about it and she said yes but he just asked if she had had fun. She didn't know what to do. She wanted to spend more time with him. She wanted him to fuck her more. She wanted to be the only one he fucked. She didn't want to get blown off when another woman came on the scene.
I told her that wasn't going to happen. She should probably find someone else. She says she didn't want that and even if he did sleep around she wanted to be with him. She just wanted more of his time. So I asked what was so special. She said he just matched her, they liked a lot of the same things and generally were a good fit. So I pointed out they were like best friends, in her mind. She happily agreed to that. I told her Chris wasn't the kind of guy that cared about that kind of thing. And he probably didn't care about her that much and that she wasn't going to get what she wanted from him.
So I told her if she wanted to get fucked regularly she'd need a sex friend for those times she want getting it from Chris. She complained she didn't want to go through the hassle of finding one and that she didn't want any troubles if the guy wanted to make her his girlfriend later on.
I was understanding and offered up my services. She was a little hesitant but asked "do you think it'll be alright?" I reassured her that I knew Chris and he was fine with it. Truth be told he had also talked briefly with me about Mako so I knew he wasn't really into her and that he didn't care if she fucked other guys.
She said ok, let's try it but she wanted to lay some ground rules. First, no sex if Chris was at home. She wanted to be with him when possible. Second, she had heard about my past from Chris so don't expect a threesome with her. I agreed and then we arranged our first meeting a couple of days later at a love hotel. The next day I talked to Chris about it and said if it bothered him I'd cancel. He said he didn't care and that was it.

On the day I met Mako after work and drove with her to a love hotel. We enter the room and we chat for a little bit. I move in to make out with her and it goes ok for a while. Then she starts to cry. I ask her what's wrong and she says she feels really emotional about the whole situation. If we fuck she knows she won't have a normal relationship with Chris. I tell her if she doesn't want to do it we can stop. She shakes her head violently saying no she wants it. She really wants it, that's why it's emotional. She then gets on her knees without a word and pulls my cock from my pants and swallows it whole. I guess to prove she really wanted the dick.
For the most part it's pretty standard sex, a lot of oral to start, 69ing, and then regular fucking. She cries a little bit more during sex but says not to worry and then starts thanking me through her tears.
During sex I ram home my dick until it hits her uterus and she grunts with a "unghh, unghh". When she catches her breath she tells me my dick is so much bigger than Chris's. I tell her I know and she says oh yeah, you shared your GF with him. While I slow fuck her I briefly explain what my sex life with Miki was like. "That sounds interesting" she says "but I don't want to do that stuff. I don't have the courage. I'm Chris's woman." I smile and ram home my cock again forcing more unghhs from her lips until she cums. I keep fucking her, getting another orgasm out of her until I finally cum. Afterward we arrange our next meeting and I drop her off at home.

A couple of days later, Chris asks me how things went and I say fine. She wasn't bad in bed, I leave out the details about the crying though. He says she told him about our meeting and that she really liked fucking me. But she would only meet me if Chris was ok with it and when he couldn't meet her. He told me to let him know when I was going to fuck her so he wouldn't get in the way. I told him don't worry about it we'll just play it by ear. And that's how it went for a bit. Mako was a trooper getting fucked by us 2 or 3 times a week. She also didn't live that close but she would often spend the night at our place.

Then a few months into our strange arrangement Chris went through a dry spell and Mako had him all to herself. Which meant I was out of luck. Now I still had some other women on the side but nothing regular. Mako had filled that role. So I was getting quite horny after a couple of weeks without sex. One night I decided I was going to get some. I knew Mako had the habit of waiting until Chris went to sleep and then going to the bathroom to clean his cum from her. I had stayed up watching TV waiting for that. When she finally comes down the stairs I walk out of the living room and intercept her. I leaned in and kiss her grabbing her bare ass from under Chris's tshirt that she is wearing.
She is startled and whispers at me "what are you doing?" I pull her by the hand to the couch and sit her down. She says "no, no, no Chris will hear us." Then she says "his cum is still inside me, do you want to fuck that? " My only response is to spread her legs. I had been sitting in my underwear so it was no effort to get my cock out and place the head against her pussy lips. I swirl it around pushing her lips around getting them to blossom as they engorge with blood. I then sink deep into her. She has her eyes closed and mouth agape as she takes her familiar friend deep inside. "Fuck" she whispers. She looks at me and says "how do you make me such a whore? I can't believe I'm fucking you filled with another guys cum." I finally talk to her between thrusts saying "do you want to stop?" knowing the answer. "No, but hurry up. I don't want Chris do notice I'm gone." I give her the quicky that she wants but was pounding her, trying to make as much noise as possible. She also can't hold back and starts moaning but between clenched lips. I thrust 2 fingers into her mouth and she greedily sucks on them. She grabs my wrist and uses my hand and fingers to fuck her face with, probably in an effort to stop the moans. I finish up and pump a load into her sopping wet cunt. She also came pretty quick. I stand above her and guide her mouth to my cock and she sucks it clean. "This time only." she says to me as she scoots by me to you bathroom. Then heads upstairs to bed.

This was the beginning of the end for Mako's rules. A couple of days later during conversation Chris brings up the fact he heard us. I say cool, I hate having to tip toe around because of her rule. He said he felt the same and that he didn't care if I fucked her the same day. So we agreed to put an end to it. We both tell her on seperate occasions that it's not fair to me to have to wait around when neither of us care. It's not like Chris doesn't know we fuck or that she sometimes spends the night with me. If anything it's just making things uncomfortable. She says she understands and agrees to do somethings about it later.

Then comes the first night after our talks. Just like normal she waits until he falls asleep and gets up. I'm waiting in my room not sure what's going to happen. I hear the door slide open quietly and look up from my phone. I smile as she walks in naked to my room. I lift the blanket and she lays beside on the bed.
I kiss her and massage her breast. She grabs my cock and slowly pulls at it. She stops suddenly and asks "Don't you think this is strange?"
"Do you mean not normal? Of course." I tell her. "But what's so great about normal? It's usually a lie anyway." I could see the worry on her face so I continue on. "I get that you're worried about what will happen. But what's so bad about this situation? It's probably not what you were looking for but the guy you want to have a normal relationship doesn't want that. I suggested you move on but you don't want that either. Also let's get real, if you were fine with the sex situation you would have probably just ignored that he was chasing other women. He wasn't meeting your needs regularly enough and that was the problem. And we both know you prefer my cock." She chirped "our sex is just different." "Yeah I know," I said "but when it comes to dick in pussy you prefer mine. I'm not saying you would ever stop having sex with Chris or that you don't enjoy it with him. Besides it's not like women never date a couple of guys at the same time. Am I right?"
She remained silent. She had rolled on her side and pushed back into my during our conversation. I took the opportunity to wiggle my cock between her thighs. She opened her legs enough so I could slide into her.
"There we go. Wet as always. Look," I whispered into her ear, "I get it. You're torn by what you think things ought to be and how they turned out. Things as they are aren't so bad. You get great sex from 2 guys you're attracted to and you get quality time with one of them that you love. It just the way that sometimes the person we love can't give us everything we need. Your choice is do you accept things as they are or do you go out and try to find that perfect guy that wants you."
Mako grabbed my hand and sucked on two fingers as her answer.

I pounded into her, immediately her pussy squelched as it was already drenched. I could feel the mixture of her juices and Chris's cum leak out of her. "That's so hot. Your leaking everything out." She slammed her ass backward into me to show me how turned on she was. As she sucked on the fingers of one hand I used the other hand to play with her clit. She reached orgasm fairly quickly. I held my dick inside her buried to the root and wiggled my hips around, stimulating her further. Mako didn't have multiple orgasms but she could cum in fairly quick succession. During the half break we were having I decided I was going to put it in her ass. Her ex-husband used to do that but she wasn't a big fan. From the sound of the stories I figured it was more because he was fairly selfish about it and just rammed it in. I went to work on her first, strumming her clit vigorously while I ground my pole around inside her. I bit and nibbled at her neck and flicked my tongue against her earlobe. Then when she seemed ready I pulled out and positioned my cockhead against her puckered asshole. At first she seemed reluctant but as I sucked on her neck she reached back and grabbed a hold of my member to guide it in. I slowly pushed her sphincter apart. "Relax, just let it in." I whispered to her. With my cock slick from her cunt I slid in easily. I fucked her ass with long full strokes, making sure not to go too hard. She played with her pussy all the while. After a few minutes her be convulsed again in orgasm. "Fuck." She cried out. "Why does your dick feel so good? It's not fair." "Do you want me to stop?" I asked her. "No." was the only answer. "Then tell me you love my cock." I chided her. "I love your cock" she said without hesitation. "Louder." I instructed her. "I love your cock!" she almost shouted in a strangled voice almost on the verge of crying. With that I went ham on her ass, pounding away trying to make the loudest slapping sounds possible. I grabbed her shoulder for leverage and just pounded away until I could feel that tightness behind my ball sack. By now she was a moaning mess. My sheets were soaked from her pussy and drool had leaked from her mouth onto the pillow. With a final stroke I buried myself all the way to the root and shot my jizz in her ass. Afterward we made our way to the shower to clean up. During the shower she asked with a concerned look on her face "do you think he heard us?"
"If he woke up probably. But who knows. You worry too much." I said. She said "by the way when a woman dates more than one guy they usually don't know each other, let alone live together." I responded, "So it's ok to keep them in the dark and manipulate them?" Again no answer. I went to my room and she to his and that was the end of that night.

From there we continued on with our little love triangle. She spent half her time at our place and half at hers. Some days meeting only one of us. Sometimes fucking both of us on the same day. Her son was happy as he and his GF got the place to themselves. Mako was satisfied as she was getting fucked several times a week, often multiple times a day. Chris was happy because he got to fuck other women whenever he could. I was happy to have another regular fuck friend, but... I wanted one more thing.
Mako had made clear she didn't want to do a threesome. She gave multiple reasons. The two main ones being she didn't want to have to handle two guys at once and she didn't want Chris to see her cum on my dick. She had had an experience with her ex-husband and his friend. They had gotten drunk and used her like a sex doll. So of course she wasn't all that into the idea.

I knew Chris didn't care either way. So I decide to make a go at it one night. Mako had come over and was spending time with Chris in his bedroom. I knew they just hung out for a while before actually having sex so I waited for the familiar sounds. After a couple of minutes I stripped naked and climbed the stairs to the bedrooms. I paused at Chris's door, heart racing. Even though we had an open relationship we had never all been in the same room together naked. I took one last breath and slid back the door. Mako had Chris's dick in her mouth and he was finger banging her. She looked up, shock and anger on her face. "I said no threesome." Mako cried out.
In response I walked over pushed her thigh aside and sucked on her clit. I could tell Chris had pushed her head down as I heard that familiar sound of dick in mouth. There was no further protest from her.
I must have worked her pussy with my mouth and fingers for at least a good 15 minutes. She finally succumbed and came on my fingers and tongue. Chris stroked her hair as she lay there with his dick in her mouth. I looked at him seeing what he wanted to do and he motioned at me to her ass. So I stood up pulled her ass over to a better position for doggy style and wiggled my rock hard dick against her pussy lips. She reached back between her legs and spread them for me. I pushed into that familiar place and held it there for a minute. Chris slid down so he could make out with her and play with her tits. I slow fucked her making sure not to jostle her so she could enjoy her make out session with him.
Chris stopped kissing her so he could talk to her. "Do you like his big dick?" he asked. "Yeah." she mewled. "It's filling you up isn't it?" he continued. She just nodded yes. I increased the power of my thrusting causing her to rock back and forth. Mako looked at Chris and and asked "Are you ok?" Her attention had gotten away from him during our fucking and she was worried he wasn't enjoying himself. He laughed it off and said "of course."
I continued to pound her from behind and she played with him with her hand and mouth. After she came again I could tell she was tired and laid her on her side. I vacated the space and Chris came over and took up the spot. I lay down on the bed beside her while Chris took his turn in her cunt. He was only half hard to start but rose to the occasion. As he fucked her, I found she was a bit more subdued. Her moans not as loud. Her motions less frantic. I kissed her and played with her nipples. I stood up and had her clean my cock. I went back to kissing her and could taste the tang of pussy juice. Chris continued on fucking her for a while. Finally tiring out he gave up on the doggy position she lay on the bed beside Mako and I as we made out some more. "You didn't cum." I said to her. "I usually cum when he eats me or with the dildo." I looked over to the side table and there it was, a little pink one.
"Why don't you get on top of him" I suggested. She rolled over and played with his half hard cock a little then squatted over him as she guide his dick inside herself. She rode him and then leaned forward to kiss him. I took the chance to get behind her and pressed my dickhead at the gap of her pussy by Chris's dick. I pushed in slowly and she screamed into his mouth as I gave her first DP. I took it slow and allowed some time for her pussy to stretch out. She adapted fairly quickly to being stuffed fully. Soon the familiar wetness came as I fucked carefully, taking care not to let my dick pop out.
I grabbed her hair to get better leverage and to pull her back into me. "Do you love being stuffed?" I asked her. "Unnggh" was her answer. "Do love Chris?" I tested "unn, yes, unn." Deciding to take it further I asked "do you love me?" She managed to strangle out, "Yes, unn, unn, unn." I reminded her "you love my dick." I could feel Chris's cock twitch under mine. Mako sounded like she was crying a little as she kissed Chris.

Soon after Chris's limp dick got fucked out of her pussy and a lot of his cum followed it, pouring out onto his stomach. With one less cock it was easier to fuck but her pussy had stretched out a little. I fucked her in different positions trying to find the best one. We must have gone on for what seemed like another half hour. Chris looked on, playing with himself and sometimes taking pictures. Finally I decided to put it in her ass. With her on her stomach when I placed my cock against the hole she reached back to spread her cheeks. I pushed in effortlessly as her ass opened up to me. It was a tight fit and we both groaned in pleasure. I fucked her that way for a bit then decided to try something new. I got her up on her knees but upright while I sat back in a weird position where I was sitting on my knees and almost sitting on her calves behind her. I could thrust up into her ass if I held my self up with an arm behind me supporting. This way Chris could see almost her whole body face on as I pumped her ass.
Chris watched on commenting, "that's hot. I never get to fuck her ass." Mako says "I'm sorry. I love you." to him. I thought I heard another note of tears in her voice. Mako furiously rubbed at her clit as she knelt in front of Chris giving him a show. Her body was a little hunched in on itself with a cock in her ass, a finger on her clit and her pinching her nipple between her fingers. She came soon enough and this time it brought me over the edge as well. Soon after I pumped my seed into her and she flopped forward, my cock pulling out of her and the contents of her ass quickly leaking out as well.
"I can see why you like to fuck him." Chris joked. She looked at him a little wounded. "I'm sorry. Are you hurt?" she asked. "No, I'm fine. I just like everyone to have fun." he told her. We all hopped into our small shower and she washed us both. I joked at her "you said you loved me" trying to get a rise out of her. I didn't expect her answer, "maybe a little but I still love Chris the most." "Well hey at least this way you don't have to choose." I answered back. We went to Chris's room and went to bed. Had another session in the morning and then she went home.

For the next few months things were good. We fucked a lot. Mako got used to the 3p pretty quick, she also got used to Chris playing second fiddle. There were a few times when just the two of them were playing, after he came she called for me to finish her off. When it was the 3 of us she would spend most of the time fucking me.

But I think I had created a monster in Chris. It wasn't just Mako. Basically every woman he managed to get was available to me. It became a pattern, he'd pick them up, they'd come over and spend a night with him then he'd proposition them. Some said no, not interested but most were down to fuck. Either with just me or with both of us.
I think he figured if they had both of us they'd stick around longer. In any case more often than not he would sit by and watch me with the women. There was a long time when we had many horny women coming by. I kind of wondered if he was bi or something, not that I cared or was interested. But he just seemed to like to watch and enjoyed passing them on. One woman was so happy to switch up she fucked me all night until everyone was passing out, then came to my room to sleep. In the morning when Chris and I were talking before he went to work she literally jumped on me and started fucking me there on the couch while he watched. She didn't pay any attention to him. Although I think she was looking to get knocked up. She kept demanding for me to cum inside her then would make statements like how we would make nice babies.

As for poor Mako, as Chris often did, he got bored with the same woman. Or rather his expectations of what he wanted were too high. He wanted a beautiful porn star to marry. But he was more like Ron Jeremy, minus the huge hog. Mako was just an average Jayshree lady. So he was around less and less when she was and it was more just me and her together. One night she spent with me in my roomwhile he fucked another woman in his. I texted him asking if he wanted to swap, hoping he'd show some interest in her, but there was no answer. I heard from him later she had known he was going to have a woman over.
Then she started to come by less and less, and she asked me to visit her instead. Finally one night after fucking me in my car, we talked about what happened with Chris. Then she asked me if I was interested in being her only boyfriend. I said I kind of was but I wasn't going to stop fucking other women. I also told her you probably don't want to be my GF. I ask a lot of my GFs. Basically I said what we did with Chris was the bare minimum. I'd probably ask get to fuck other men and women, including strangers in public. She said she understood but couldn't do that and didn't want to meet anymore.

For a while Chris and I enjoyed various women. You can see a clip of one in my video section.
I also propositioned some of the women I picked up as well, but most weren't interested in him. One Filipina said she didn't mind if he watched. But he flaked on the one time she was willing to do it. Mako did hit me up every one in a while for some cock but it was always just a one off. She had met another guy as well. I teased her about her cheating and she said she was spoiled now and couldn't settle for one cock. She said maybe. I think she was teetering on the edge of giving in to my conditions but was waiting for me to make the final move.

In the end one woman finally nailed Chris down. His current wife, Yumi. A BBW who came from a well off family.
Yes, as you probably guessed I managed to fuck her as well. She had turned down the 3some but later on gave into my flirting. While she thought she was cheating on Chris, I was giving him the details. Later on Chris had arranged for her to invite her girlfriend so the four of us could spend New Year together.
That was the girl Miku who I already talked about, the natural submissive. It was an interesting night. Basically I was flirting with Miku and Yumi would get angry. Chris would also flirt with Miku but didn't get the same reaction. But then I would pay attention to Yumi again and squeeze her tit or ass when no one was looking and her mood would lighten up.
Perhaps one guy noticed, an Indian guy came over and started hitting on her until everyone told him to fuck off. We end up at Yumi's place, I knew by now this was Chris's plan and when I had a moment alone with Yumi I felt her up, played with her pussy and made out with her briefly. She seemed happy for the attention but ultimately put a stop to it. In the end though the girls put a stop to all our advances saying "we know what you want and it's not going to happen" so we all just went to sleep.

Anyway later Miku and I hit it off and Yumi got in a huff because, I found out later from Miku, she had been thinking of dumping Chris for me. And she claimed Miku had stolen me from her. We figured she was also trying to set Miku up with Chris. Her conniving had back fired on her. Things could have been much better if she had just given in.

In any case a month or two later Chris had knocked Yumi up and they were soon married. I had hoped Yumi would come around and that we could maybe do some swapping. I had already gotten Miku ready for that. But it wasn't to be. Chris is now in a loveless marriage and I still hear occasionally. I should have stayed with Mako.

Chris was a true cuck. And we should be thankful there are guys out there like him.

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Cuck, Chastity, Femdom/Feminisation.(If I get enough good feedback I will supply parts 3-4)(Also very interested in writing bespoke stories to whatever specification the reader desires. Leave a message detailing your kinks/character names & desired situations and I’ll get back to you. No Under 18 stuff, it’s ridiculous but in Britain you can apparently be punished for fictional thought crimes. Orwell was right!)Part 1.I serve my mistress, holding the stockings and heels. She sits on the...

2 years ago
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Cuck Hubby In Chastity

CUCK HUBBY IN CHASTITY by Throne Being locked in chastity can do plenty to a man. The longer he can't get free, the bigger the changes. "What do you think of these?" Bella wanted to know. "They're called Date Panties. 'Cheeky' style. Because they leave my butt cheeks showing." The curvaceous woman turned around so her husband could see the rear view. He opened and shut his mouth, throat so dry he couldn't speak. She was extremely sexy, with her long red-brown hair, generous bust,...

3 years ago
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Cuck Fetish real story

ok story time xD (bear with me)hmm i believe i got into this fetish by watching some porn of it.my BF is Asian and very passive. he doesn't take what he wants and is too gentle. he is not very large down there either. but im not a size queen or anything at that doesn't really bother me too much.but its the fact that hes not very manly. he cant grow a nice sexy beard and doesnt have body hair. so hes not very masculine. this is probably the tipping point where i succumbed to this fetish. me and...

4 years ago
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Cuck Father

Reed was home from college for the summer. His room had been converted to an office for his milquetoast father. So the young man was forced to convert part of the attic into a bedroom. ‘That’s fine.’ He thought grumpily. ‘Not like I could bring any tail back here anyway.’ He was moving some boxes when one split open. The old cardboard ripping. Grumbling he picks up a collection of old books, paper, art supplies, an old camera. He stops when he notices a photo on the ground. It looks like a...

2 years ago
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Katiersquos Roommate

Katie’s Roommate1 Katie KendalKatie Kendal was extremely proud of the fact that for more than three years, she lived by herself in an rented house and paid all the bills on time. It was difficult, and at times she barely made ends meet. Worse than that was the fact that she was terrified of being alone. It had been the most difficult decision she had ever made when she decided at twenty years old to move out of her parents house and into the real world. She hated living by herself but she knew...

4 years ago
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iPad Roommate

“Pffff, another sweater.” Aaron says as he holds up the red, green, and white Christmas garment is aunt sent him. “At least this one as an actual cool design on it.” Ian says as he smiles at his roommate. In a small house in a secluded neighborhood covered in snow, two men in their mid-20’s enjoy a simple holiday together. With the pandemic still at large, both guys have spent their family time on their laptops’ cams. Wishing their loved ones Happy Holidays and having shipped their gifts to one...

3 years ago
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Sarahs New Roommate

Sarah's New Roommate By Bill Hart "You're very beautiful." Mike pulled the young girl he'd just met in the bar to him again and kissed her. "But I'll bet you already knew that," he smiled, even as Sarah blushed. "How could you not know how beautiful you are, Sarah Jennings?" Sarah continued blushing. No one other than her grandfather had ever called her beautiful before. She wasn't entirely certain why she'd gone to the bar; she wasn't altogether sure why she'd brought Mike home...

3 years ago
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The new situation with a dominant roommate

So if you read my last story then you know the situation...if not a quick summary would be that I have a female roommate who turned out to be very dominant and has joined me and my girlfriend in our sex life.Ok now the new dynamic of the relationship is that me and my girlfriend are still together and everything is normal, except that sometimes my roommate would join us in bed or act in a dominant way with me every now and then, overall its a really good situation although I'm sure it's going...

2 years ago
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Finding a Roommate

The year after I finished college, I took a job as a junior management trainee in a stock market firm. I hated everything about the job, but it paid my share of the rent while I got my screwed up brain together. One Saturday, a female showed at our door, asking if we would consider a girl for the roommate opening we had posted. She looked presentable, and I invited her in to meet Sean, my one remaining roommate. The lease was in my name, and it wasn't a good time of the year for finding...

2 years ago
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Alice and My Roommate

Alice and I were rolling around in the sheets of my dorm room. She and I had vibrators inside us and we were holding onto each other’s toy – pushing it in and out of soaked swollen pussy. Anyone who has ever felt the odd sensation of something so desired, so thought about, so hoped for, finally complete – anyone who has felt that, could know what I was feeling. My virginity was gone. I felt like a bird released from her cage, and I lavished everything on Alice. I wanted to give everything to...

2 years ago
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Alice and My Roommate

Alice and I were rolling around in the sheets of my dorm room. She and I had vibrators inside us and we were holding onto each other's toy – pushing it in and out of soaked swollen pussy. Anyone who has ever felt the odd sensation of something so desired, so thought about, so hoped for, finally complete – anyone who has felt that, could know what I was feeling. My virginity was gone. I felt like a bird released from her cage, and I lavished everything on Alice. I wanted to give everything to...

Lesbian
3 years ago
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My New Roommate

About six months after my divorce, I decided to accept the company’s long-standing offer and transfer to New York. Being a small-town guy from the Midwest, I was a little intimidated about moving to such a big city, but I felt like the change would do me good. Most of my friends had been my ex-wife’s friends first, so I was beginning to feel isolated. If some woman had come along in those six months to pique my interest, I might have stayed longer to see if the relationship might go somewhere,...

Gay Male
3 years ago
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Charlenes Roommate

Charlene was dressed like a high-school girl, and a prudish one at that - white blouse buttoned up to her neck and tucked into a pleated gray skirt that came down almost to her knees. Not that the skirt length made much difference with her legs being totally covered by white stockings.Tommy wasn’t even sure he wanted to admit knowing her. And such a shame too, he thought. Charlene was a pretty girl – not too short and not too tall, petite, but shapely, blond hair to her shoulders, blue eyes and...

College Sex
4 years ago
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Charlenes Roommate

Charlene was dressed like a high-school girl, and a prudish one at that - white blouse buttoned up to her neck and tucked into a pleated gray skirt that came down almost to her knees. Not that the skirt length made much difference with her legs being totally covered by white stockings.Tommy wasn’t even sure he wanted to admit knowing her. And such a shame too, he thought. Charlene was a pretty girl – not too short and not too tall, petite, but shapely, blond hair to her shoulders, blue eyes and...

College Sex
1 year ago
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Watched by My Roommate

My wife and I had been dating for about three months when I got a new roommate. Jason was decidedly gay, though he did a good job of covering it up. As far as roommates goes, he wasn't a bad one at all. Most weekends he was gone and didn't come back until late Sunday evening, so on those weekends that Laura and I were strapped for cash and couldn't afford a hotel off base, it was nice to know that we had some privacy in my room. Because it was a training command, having a guest of the opposite...

Bisexual
3 years ago
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The First Time I Secretly Recorded My Roommate

I wanted to share another story, about the first time I secretly recorded my roommate. By this point we had been living together for over a year. I had the pleasure of listening her have sex with various guys on a number of occasions. It still didn’t happen often as she often waited until I was out of the apartment (between that and the cleaning she really was a courteous roommate).On the few times she had come home with a guy for sex, I had taken to listening behind my door. I would bring a...

2 years ago
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Cucked on Vacation

Not my own property. Taken from literotica to add pictures and make it customizable. The original link is https://www.literotica.com/s/cucked-on-vacation. It was our first proper vacation in years. I breathed a sigh of relief as I gazed out our suite window towards the calm ocean waters of the gulf. After seven years of marriage and a limited amount of time off it felt therapeutic to finally have a week away all to ourselves. We had selected Naples because it was quiet, and peaceful, and a...

Interracial
4 years ago
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My Sissy Roommate

I swear he’s always like this. So worried about everything. I don’t know how the kid has survived this long. Probably because I’m always here to calm him down. It’s kind of funny, not many people can see Andrew and me as being friends. Him being a meek, petite, nerd who’s often confused as a girl and me a muscle-bound, jock who gets all the girls. We’re complete opposites from each other. And yet, Andrew and I have always been best friends. We grew up next door to each other, I’m always...

2 years ago
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The Sexy Roommate

Eighteen-year-old Katherine Sparks moved into her dorm room to find gothic-looking posters up on the right side of the room. She planted her box of stuff on the single bed on the left. A busty pretty girl with long black hair in a black skirt and short cut top with heavy gothic makeup on walked in. She turned to her."Hi, you must be my roommate, I'm Nina Davis," she said and shook Katherine's hand. "Katherine," Katherine replied. Her blue eyes lingered down to her roommate's bust and...

Lesbian
4 years ago
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The Roommate

Chapter 1: Doin' The College Thing It's hard to believe you finally did it. You really made it to this point in your life. Have you actually gone away from home? Have you actually come to college? Are you actually standing in your own room at Western State College? You can't believe it. It seems like only yesterday that you started High School and suddenly you are out on your own and moving into your own Dorm room. You're not sure you are really ready for this. In fact, you aren't even sure you...

2 years ago
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Life Gets Better Part Two The New Roommate

 Brian looked down at Stacy. He couldn't believe he might be fucking these huge tits for the last time. The two of them had a good thing going on between them for these past three months. They both had decided not to put a label on their relationship. Instead, they just enjoyed each others company, as well as fucking each other to the point of exhaustion. All of that would have to was on hold for now. Stacy and her ex-husband had agreed to go on a long trip together. It was their last attempt...

Interracial
1 year ago
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My Girlfriends Roommate

Back in college I was dating this girl Shannon. She was on the school volleyball team so she was in incredible shape. The only problem was that, during the season, she was often busy, and when she wasn’t busy she was tired. This often left me lacking when it came to sex, and I would often be left to take care of myself. When she wasn’t in season, though, she could and would screw me until I couldn’t take it anymore. I think it was part of her off season training plan to stay in shape. After a...

College Sex
4 years ago
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My Sons Roommate

Something happened to me not long ago that altered my life. I am not a gayman. I have never liked gay men. I could never imagine how a man could besexually attracted to another man. It's unnatural. I always believed thatit surely must be against God's will.When my son, Mike, moved into his dorm room at college during his Freshmanyear, his mother and I visited him to make sure he was comfortable and thatall arrangements were satisfactory. We met his roommate, Tom. He seemedvery nice, and...

4 years ago
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Mind control of roommate

As I approached the dormitories at the beginning of my sophomore year, I have to admit I wasn’t entirely happy. I’d had such a great roommate my freshman year that I wasn’t looking forward to a new one. No, it wasn’t what you’re probably thinking. My previous contentment had nothing to do with sex, since Gerry had been totally straight and not at all physically my type; but he was smart, funny, neat, and tolerant, and, in short, perfect to live with. When he decided, over the summer, to get an...

2 years ago
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THE ROOMMATE

Foreword: This entry is a direct continuation from my previous stories. Basically I’m just telling all of the most interesting and exciting sexual stories of my life in chronological order. I will try and include enough back story for a new reader to be able to jump right in, however I apologize if I fail to provide enough. In short, if you want to get the full effect, you may want to read the entire thing from the beginning. Thanks and enjoy. The RoommateJune 2002In the summer of 2002, I was...

4 years ago
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My Sissy Roommate

“Relax, Andrew. It’s just a party. Yeah, sure there will be girls there, but it’s not like they’re serial killers or something,” I tell my best friend as we make our way to the party. I swear he’s always like this. So worried about everything. I don’t know how the kid has survived this long. Probably because I’m always here to calm him down. It’s kind of funny, not many people can see Andrew and me as being friends. Him being a meek, petite, nerd who’s often confused as a girl and me a...

4 years ago
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My Best Roommate

You hate your job. You hate the long hours you have to work. You hate your fat, sweaty, incompetent boss. You hate the work you do and your clients' demands which are equal parts incessant and annoying. You hate that your job pays too well for you to quit. However, despite all the bullshit you put up with, your week is finally over. And working there has paid off in at least two ways. The first comes in the form an apartment that qualifies as more than just "okay." The huge living room packed...

2 years ago
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Raped by drunken roommate

This incident happened when I was staying with my bachelor friends. It was a 2 BHK flat where there were 5 boys staying together including me. We used to have drinks almost on a daily basis and were enjoying our lives as roommates, but none of us were involved in sex with each other as there were no gays in the group.We had 3 spare keys for the main door and any of the 2 roommates would keep each of them, and last key, we normally keep in the nearby bakery to avoid any last minute confusion...

3 years ago
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My College Roommate

I arrived at my university in Colorado in late August for my freshmen year of college. Orientation and classes were starting and I was eager to meet my roommate. Lee had been on campus all summer prior to me arriving. He was a Linebacker on the football team and was also a true freshman like me. Lee was up early each morning and very busy each day but had time to help me with orientation, building locations, and introducing me to other guys on the football team. He seemed like a great roommate....

3 years ago
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My Sons Black Roommate

I was a forty-six year old trophy wife, even if I do say so myself. I work out three to five days a week to stay fit. I am five-feet-four inches tall and I have a 36D 28 34 body shape. My husband is a senior vice-president for a Fortune 500 company and he travels a lot.Recently he left on one of his week long trips. I decided to visit my son, Mike, at his college where he is a senior. I took a hotel room near his apartment. He and his roommate talked me into going drinking with them.His...

MILF
1 year ago
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How I Became A Sissy Roommate

Hi this is Jeet from Mumbai. It was the end of my 12th boards and I had gotten admission in an engineering college in Pune. It was always my fantasy to be a sissy slut for a guy and so I began to find people online who were looking for roommates on planet Romeo a gay social website. I found a guy named Paras who had a flat in Pune which was near my college and he wanted a roommate to split the rent. He was a 23 year old dominant top and wanted a bottom as a roommate. We discussed the rent and...

Gay Male
3 years ago
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My College Roommate

I arrived at my university in Colorado in late August for my freshmen year of college. Orientation and classes were starting and I was eager to meet my roommate. Lee had been on campus all summer prior to me arriving. He was a Linebacker on the football team and was also a true freshman like me. Lee was up early each morning and very busy each day but had time to help me with orientation, building locations, and introducing me to other guys on the football team. He seemed like a great roommate....

Gay Male
3 years ago
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The Cuck and the Roommate

Kevin and Jenny were high-school sweethearts. They'd met in their small town in the suburbs, becoming friends at 12 before they started dating at 15. They had stayed a strong couple through all of high school, growing as people and developing together - they had stuck with each other through thick and thin. They were each other's firsts in everything - both had only ever slept with the other. College was the next big adventure - they'd made a point to apply and enroll at the same state...

3 years ago
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Fucking my roommate

When I returned to the states, in 1967, I spent a few years bouncing around in a few jobs; nothing that I would make a career out of but they supported me pretty well. I made new friends and had set up camp in the big city of Pittsburgh. I won’t go into all of the details but one of the friends and I wound up sharing an apartment for a while. Tom was a nice enough guy but straight; I was trying to get laid every chance I had and, if he wasn’t so straight, he would have made a nice fuck buddy.We...

2 years ago
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Beginning Of Sexual Relationship With Roommate

This is a gay story about how I got in a sexual relationship with my roommate. I was studying in a college in Bangalore. As it was a long way from home, I stayed at the college hostel. I had a roommate. He and I were like buddies and we were in the same class. I never had a gay experience in college or hostel before. One day, after class, we went to our hostel. After getting into my room, we placed all bags and stuffs on the table on the side and he said he will go out and buy some snacks for...

Gay Male
2 years ago
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Vidhi8217s Diary 8211 Chapter 1 8211 Hot Lesbian Experience With Roommate

Hi, this is Vike back with another story. Theh heroine of this story is a 19 year old girl named Vidhi coming from a very conservative family belonging to a small town of India. Since her childhood, she has been studying in a girls’ school. And belonging to a conservative family, she was never allowed to talk to any guy apart from her younger brother. Vidhi was a studious girl, always scoring above 90% in every exam. She completed her 12th and now she had no choice but to move outside her city...

Lesbian
2 years ago
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Naughty Roommate

I been living with the same roommate for the past 4 years and were best friends, well now he got married and I have this townhome all to myself but I need a roommate to cover the cost of it. It’s a big place and I can’t afford it by myself, so I start asking around. A friend says her girlfriend is looking for a place since she just moved to the city. I didn’t hesitate and told her to come by.The following day she came over to see the place. Her name was Carmen, she was the sexiest girl I ever...

1 year ago
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Roommate

I just had graduated college with a 4.0 GPA and a degree in history, applied to the Smithsonian in D.C and got offered a job. I'm a twenty two year old virgin, but not because of my looks, I'm told I am a good looker, with a decent rack, 34 C, but because I have been programmed since childhood to excel in school. I did just that, all through my school life, studies came first, which left little or no time to party and here I was in Washington D.C. Apartment hunting, preferably with a roommate...

Lesbian
3 years ago
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The Roommate

I’ve had half a dozen roommates in the last 15 years, some for months, some for years. Sean stayed with me for about 4 years. All my roommates were in recovery, and staying here provided a chance to start rebuilding their lives when they had to start from square one again (cheap rent and all utilities included). He was a good looking guy, 6’1”, good physique, beautiful blue eyes and the sexiest smile. He was friendly, courteous and gregarious. Because so many of the roommates had next to...

Gay Male
4 years ago
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Swapping Girlfriend For Her Horny Roommate

Introduction: Coeds Swap Boyfriends as Graduation Present This is a true story. I met my wife, Mary, in college. She was a gorgeous, shoulder-length brunette with long, slender, curvy thighs and calves, 32-C tits just big enough to flap delightfully when she humped, and a very pretty, slightly freckled, pale Map of Ireland face. Although we didnt fuck on the first date, we did have a long and enthusiastic make-out session in which I got all the way to third base. It wasnt long before I raced...

3 years ago
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Cuck and cucked

________________________________________The events I describe occurred nearly forty years ago, pre computer and mobile phones, but they still get my seventy plus year old cock hard whenever I recall them.Carol had long dark curly hair, a figure to die for, slim waist, and 34D tits. We met after I’d answered her advert in a magazine contact. That’s the way recreational sex was organised in those days. Arrangements were made for me to visit her on a night when her partner, Paul, was away from...

3 years ago
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Cucked at a wedding part 2

Cucked at a wedding part 2 - you can read on if you want but my other cuck posts set the sceneAs the evening wore on Carrie and I danced together - my cum filled boxers had dried out. 'You can say if you don't want me to go back to his room Dan. ' Carrie whispers as we hold each other close. I pull her closer, my cock hard against her. 'No go - it will be fun. We will never see him again and I can tell you want his cock.' I smile at her and kiss her deeply.We had back to the bar for another...

3 years ago
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Cucked for the first time

Cucked for the first timeCarrie and I had been fantasising about her fucking other guys for nearly a year - I wouldn't say it dominated our sex life but it was always a thought not far away. We had even talked about it in a practical way over dinner a few times, how it would happen, what we want don't want etc. She didn't seem keen on an actual date with a guy, although I must admit the thought of seeing her get dressed up to go out with someone does get me very hard.Anyway, back in February it...

4 years ago
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The Wayward Roommate

THE WAYWARD ROOMMATE by Skip Part 1 By all rights Lisa McGrath should have been one oversexed 19-year-old slut.But to the contrary her propensities were such as to make her repulsive toher peers' of both sexes and especially to her 28-year-old roommate JeanineApplegate. Lisa and Jeanine were roommates in a single family home in a Delaware Countysuburb of Philadelphia each having their own bedroom but sharing the rest ofthe house. It was owned by Jeanine's elderly Grandmother who resided at a...

4 years ago
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Janices Roommate

 J got up. “I’m going to take a shower, I won’t be long, stay here,” she said, wrapping a towel around herself and walking out of the door. The door didn’t latch when she shut it. Instead, it opened just enough so that I could see into the hallway. Not long after the shower started, J’s roommate walked down the hall. She was wearing a different shirt, it was shorter. She had a thong on, and now I could see all of her ass. She had the most perfect ass I’d seen in a long time.I laid in J’s bed,...

Quickie Sex
3 years ago
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College Dorm Roommate

When I was a young teenager, I had several experiences with an older man. I'm not necessary gay and am not sexually attracted to men, but this guy got me into cock and cum. Let me tell you, that no woman can suck a cock like a man. Men are simply better at it. But there is something about a nice hard cock with a big mushroom head that makes me hard. Hearing a man moan and feeling his cock pulse in your mouth as he's getting ready to shoot a nice creamy load into your mouth is incredible. The...

3 years ago
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The Roommate

Here I m desiboy, back again with another story after fucked my teenage love. Thank you all for showing your support and I will work on the other aspects also to improve. Suggestions are welcome at [email protected] this story is about one of my encounters with a roommate. It happened when I was doing an internship in a Gurgaon firm. Commuting to Gurgaon from home was the hell of a task as most of my time was spent in traveling. So I decided to take a flat in Gurgaon. I did all the...

4 years ago
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The Roommate

Jamike and Buchi had been friends since they were k**s. Once they got into college they decided to get this house out by the university so they wouldn't have to live in the dorms. Only problem was they wanted one more roommate so they could lower the cost of bills. After looking up other people needing a place to stay Jamike came across Zoba in an online search. She was moving to the university on a dance scholarship. From her picture he could tell she was pretty with brown hair to her...

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