Getting Started Cucking – The Roommate free porn video

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Eventually the summer had to end. Annie had another two or three encounters with the guy (at least I assume it was him), but she didn’t invite me along for any of them. So I guess she’ll have to be the one to tell those stories.

In August we went away to college. We were both enrolled at the same large, midwestern university, and we were both living in the dorms. Dorm life didn’t end up agreeing with either of us. If nothing else, there was next to no privacy in those places. We had enough trouble sneaking quickies in between the two of us, let alone trying anything more adventurous.

By mid October I gave up and found an apartment off campus. Annie still technically lived in the dorm, but in reality she moved into the apartment with me.

“Apartment” was a generous word for the place. It was in an old house that had been awkwardly divided into lodging rooms. I found the place via a friend of a friend named Jeff, who was looking for a roommate. The space turned out to be the house’s attic at the top of a steep staircase, two small under-the-roof rooms with a small common area.

Annie’s parents gave her a fairly generous allowance that kept us in rent and food money, with enough left over for some creature comforts and some alcohol. We had been liberally partaking in the latter one evening when she suddenly shifted the conversation away from a drunken debate about movies.

“Hey, can I ask you guys to do me a favor?” she began.

Sure, we both nodded, being in favor-granting moods.

“It’s kinda hot up here,” (which it was). “Would it be okay if we took off our clothes?”

Jeff looked at me, and I looked back at him.

“We can leave our underwear on, of course,” she added. Ain’t gonna lie, that was a little disappointing.

But I wasn’t disappointed for long. Naturally we both agreed. This was back in the day when tighty whities were still a thing, so I can’t say that either guy looked super sexy. Still, Jeff was tall and lean, and his underwear showed off his assets (especially because it looked like he was already getting hard).

Annie, on the other hand, came prepared. Her undergarments turned out to be a light blue, lacy bra and panties that left very little to the imagination.

We poured another round of drinks and resumed our passionate debate about whatever we were passionately debating. Of course Jeff couldn’t keep his eyes off Annie, pretty obviously talking to her chest rather than her face.

“Do you want to see them?” she asked in mock exasperation.

He nooded.

She unhooked her bra and let it fall away, giving him a real eyeful of her big, round tits and pale pink nipples. At this point he was more than just kinda hard, and it looked like he would meet her meat requirements quite nicely.
Annie shook her boobs back and forth a little. Jeff actually moaned out loud.

“Here,” she said. “Let me show you the rest.”

With one smooth twist she yanked her panties down, leaving them dangling from one ankle. She leaned back on her elbows and spread her legs, giving him a flawless view of her neatly trimmed bush and damp lips.

Jeff took a long look at her. Then he looked at me.

“So what’s the deal between you two?” he asked.

She answered. “He just watches.”

Without another word, Jeff stood up. There was barely enough room for him to do so under the low, angled ceiling. Annie got up on her knees in front of him. Ever so slowly she slid his shorts down, finally allowing his cock to spring free and come to full attention.

He met her standard. Nice and long and thick. He had a particularly impressive cock head, big enough that it made his manhood look like a long-stemmed mushroom. Annie was in for a good time.

She kissed him. She licked his balls. She ran her tongue up and down his shaft and then around and around his thick cock head. Then she opened wide and took him into her mouth.

The braced his arms against the low slope of the ceiling to steady himself while he began to rock his hips back and forth, slowly shoving himself deeper into her. Thanks to her weak gag reflex, she was actually able to swallow him all the way to the base, leaving his cock down her throat for what seemed like forever and only choking a little when she let him back out.

Eventually he started to moan like maybe he was getting ready to cum. She wasn’t ready for him to release that soon, so she stood up, wrapped her arms around him, pressed her naked body against his, and gave him a deep kiss.
Oddly, watching her kiss him gave me a strange feeling in my stomach. Sucking his cock was one thing, but the kiss seemed more emotional somehow. More affectionate and romantic. It gave me a small shock of jealousy, which in turn made my cuckolding a little more intense.

At that point Jeff took control. He pulled her over to the bed, a rickety double in a shadowy corner of the room. He practically threw her down on her back and then practically threw himself on top of her. Shoved her legs apart. Shoved himself in. He fucked her hard and fast for a minute or two, let out a loud grunt and came inside her.

He left himself in until he lost his erection, making sure to leave every drop inside her. Then he got up and left, pausing to say “She’s all yours” on the way out.

I stood at the foot of the bed and waited for Annie to give me a clue about what would happen next. Would she want me to jack off as I’d done in the past? Would she let me do some actual “sloppy seconds” fucking?

Turned out there was another possibility I hadn’t even pictured.

“Eat me,” she said.

I almost protested that her pussy was full of another man’s cum and I didn’t want that in my mouth. But then I thought better of it. First and foremost, our developing arrangement had me doing pretty much whatever she said, and it seemed unwise to buck the trend at this point.

But more than that, I noticed that the thought of licking Jeff’s cum out of Annie’s pussy gave me a kinky thrill. A powerful one. So I nodded in agreement.

She spread her legs apart, and I lowered my face down between them.

I’d gone down on her before, so I was used to her sweet, musky flavor. The new scents and flavors – a much more pronounced saltiness – were incredible, almost overwhelming. The more I licked her, the more sperm seeped out. I eagerly ate it all, reveling in the thrill of enjoying my first cream pie.

The oral attention got her aroused again, too. So she let me fuck her. I was so excited that I didn’t last long. My orgasm was a real earth shaker, and I passed out almost immediately after coming.

I woke up some time later. The first thing I noticed was that Annie was no longer in our cramped little bed. The second thing I noticed was the sound of moaning from somewhere else in the apartment.

Of course she was with Jeff in his room. They left the door open, no doubt in case I awakened and wanted to watch. He had her on all fours in his bed, and once again he was giving it to her really hard.

My intent was to stand back in the shadows so they wouldn’t know I was there. But the apartment was new to me, and I didn’t yet know all the spots on the floor where the boards creaked. I made enough noise to temporarily distract them, and they both looked over at me standing in the doorway.

Annie held my gaze for a moment and then went back to staring straight ahead as she took him deep inside her. Jeff, on the other hand, kept looking at me as he kept fucking her. He even smiled, sort of a “check this out” expression as he began to slam himself into her even harder than before.

And like before, he came inside her pussy. They snuggled for a few minutes, hot and sweaty and naked together in his bed. Then she kissed him goodnight and rose to take me by the hand and lead me back to our bedroom.

Once again she stretched out on her back and spread her legs wide. This time she didn’t even have to tell me what to do. The walk in from the other room allowed some of the semen to dribble down her thighs. So I licked it off her skin before turning my attention to the main course.

Once she was satisfied that I’d gotten it all (and given her an additional orgasm as well), she closed her legs, rolled over and went to sleep. I don’t know if she heard me jerk myself off in bed next to her.

For the next few weeks I spent a lot of time eating a lot of cum. I got plenty of cream pies, and I also ended up licking it off her face and / or tits several times. One thing Annie loved to do was to let Jeff fuck her while I was out of the apartment. She’d let him have her pussy until he was close, and then she’d have him come in her mouth. When I got home they’d both act like nothing had happened. But then she’d give me a big kiss, allowing me to taste what I didn’t get to watch.


The rest of the story is less sexy, so if you’re just here for the thrills you can stop reading now.

Alas, all good things must come to an end. The three of us spent so much time having sex and goofing off together that none of us spent much time going to classes. As a result, Annie and I ended up needing to take the spring semester off to get our shit together.

We stayed friends with Jeff, and a couple of years later he came out as gay. It kinda explained some of his bedroom behavior, particularly his roughness in the sack (as if he was still trying to prove to himself that he actually liked sex with women). This was back in the 80s when HIV was more common and more lethal than it is now, and unfortunately it eventually took him.

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Julie out on her own ndash Bowling Aftermath ndash CDTVT

Julie out on her own – Bowling Aftermath – CD/TV/TS, MMSo last time I wrote about how my roommate Mike hooked up with flirty Vicky at the bowling alley, how I knew about it, how Mike knew I knew, and how Vicky knew I knew, but how Vicky didn’t know that Mike knew I knew. Confused? Read last entry!Anyway, when Mike and I got home that night, we thought it was hilarious how Vicky’s horny lusts had gotten the better of her, how she’d blown Mike in the bowling alley men’s room while I watched over...

4 years ago
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Red ndash Part VII ndash A Quick Trip

Sara was jolted from her nap when the phone rang. She glanced over at the kitchen clock. It was 6:15pm. She’d been studying hard since school started three weeks ago and had passed out in the process. It was her trucker friend, Cliff. “Hey babe, I’m coming north on 95 and was wondering if you’d like to meet me at the truck stop up above Richmond?”Sara could feel pussy waking up faster than she was. It quivered in her fleece shorts. “Ummm, yeah, sure. How long before you get there?”“Probably...

3 years ago
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Julie out on her own ndash with Mike and Vicky ndash CDTV

Julie out on her own – with Mike and Vicky – CD/TV/TS, MMSo last time I wrote about and my roommate Mike, how we’d come to terms with my crossdressing, my attraction to him, and his willingness to have a horny busty T-girl go wild on him.Since we both were comfortable with it, as time went on, I began staying dressed more in our apartment. Nothing fancy, but during evenings and practically all weekend, more often than not, if I had no immediate plans to go out, I would wear the following. Pink...

4 years ago
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Julie out on her own ndash more with Mike ndash CDTVTS

Julie out on her own – more with Mike – CD/TV/TS, MMSo last time I wrote about my first sexual experience with my roommate Mike, how I’d “ambushed” him when he came home one night, and I was dressed like one of our sexy busty slutty blonde friends, Vicky. The next morning, I was awake and eating breakfast in our kitchen (not cross-dressed), just in shorts and a t-shirt, ready to do some weekend chores.Mike came in behind me and cleared his throat nervously. He said, “Um, did what happen last...

2 years ago
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Julie out on her own ndash with Mike ndash CDTVTS MM

Julie out on her own – with Mike – CD/TV/TS, MMLiving with my folks was OK, but when I finished college, like most k**s, I got a decent job and was eager to get a place of my own and taste more freedom … and COCK! (Well, most k**s want to taste opposite gender genitals, but you know what I mean.) Several of my friends had moved out earlier than I did, having not gone to college for a full four years, some not having gone to college at all, yet getting decent jobs through what they knew and/or...

2 years ago
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Julie out on her own ndash with Mike ndash CDTVTS MM

Julie out on her own – with Mike – CD/TV/TS, MMLiving with my folks was OK, but when I finished college, like most k**s, I got a decent job and was eager to get a place of my own and taste more freedom … and COCK! (Well, most k**s want to taste opposite gender genitals, but you know what I mean.) Several of my friends had moved out earlier than I did, having not gone to college for a full four years, some not having gone to college at all, yet getting decent jobs through what they knew and/or...

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