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My Roommate

Category: Group Sex
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My roommate Jessica was beginning to be a bit of a drag. Slightly frumpy and conservative, she had a problem with me bringing boyfriends home on a regular basis. She constantly left me notes requesting that if I wanted to have “absurdly loud intercourse on a bi-nightly basis” (as she put it), I should have it at my partners’ houses and not at our apartment.

I began to do just that, simply to avoid listening to her complaints.

One day, my boyfriend Charlie and I were discussing having a threesome with another woman. We were both sexually adventurous, and I thoroughly enjoyed being with beautiful women. We decided the easiest and most discreet way to meet a woman was through the internet, so together, we began to cruise the online hookup sites.

You can imagine my shock when I came across the personal ad for “Jessi”, who was looking for a “clean yet dirrrty couple to share wild nights”. The woman in the picture was dolled up and dressed in black lace, but it was, without a doubt, my roommate Jessica. The ad also claimed that it would be her first time having a threesome.

Somewhat out of spite, somewhat out of curiousity, I replied to her ad, giving her a fake name, and sending a picture of another couple that we found on the same website. We set up a date for Friday night at (gasp!) MY apartment. I wondered how she was going to explain it to me!

On Friday morning as I was getting ready for work, she told me that her parents were coming over for dinner that night. It was a clever move, she obviously remembered how boring I thought her family was, having met them a few other times when she’d had them over for dinner. I told her I was sorry I couldn’t make it, but that Charlie and I had tickets for a new play that opened this weekend. She left for work, wearing a frumpy beige outfit and ugly beige flats. Her hair was limp, she looked much older than she really was.

That night, Charlie and I got ready for our “hot date”. I wasn’t sure what I was even going to do yet, whether I would attempt to go through with it even if I had the option, or whether I would just show up and laugh in her face, but despite my indecision, when the time rolled around, we headed over.

I knocked on the door to my apartment, and when it opened, I was absolutely in shock. My typically frumpy roommate looked a hundred times better than she had in the picture in her online ad, and a thousand times better than I’d ever seen her. She was wearing a simple long black satin nightgown and her hair was up. She looked elegant, beautiful and EXTREMELY sexy. She also, of course, looked shocked and humiliated to see me.

“What are you doing here!?!?” she demanded. I smiled slyly and said, “We’re your date”. Charlie stepped in the door behind me, and I could tell by the look on his face that he was excited. She stammered and obviously wasn’t sure what to say. I decided, instead of using words to try to convince her, I’d just kiss her….

Her lips were soft, unwilling at first, but as I stroked her shoulders, she began to reciprocate. Charlie stepped around behind her and kissed her neck and began to stroke her breasts. I could not believe she was going along with this, but I was really starting to get into it. Before long, we had moved into her bedroom, and clothes were beginning to fall off.

I reached my hand up under her nightgown, and was slightly surprised to feel no underwear, but rather, a moist and engorged pussy. I pulled her dress over her shoulders just as Charlie pulled my underwear off me. He began to massage my clit as I gazed adoringly at hers.

Her pussy was beautiful, shaved and very pink. It glistened with her juices. I looked at her face as I slipped one finger inside her. She still looked shocked, like she wasn’t sure what was going on, but as I began to massage her, that expression began to melt into one of ecstasy. I gazed at that beautiful pussy, and could not help myself; I needed to taste it. I dipped my tongue in, and the initial sweet saltiness of her juices caused my own pussy to contract. Charlie had moved away from my pussy and on toward Jessica’s breasts. As he licked and sucked her nipples, I began to seriously eat her out. I slipped another finger in as I wrapped my lips around her clit and sucked. She began to moan as I alternated flicking her clit with my tongue and sucking it hard with my lips, never neglecting her internal massage with my fingers.

I felt her orgasm coming before she did, I think, because she looked and sounded shocked at the oncoming pulsations. I didn’t stop while she came, but afterward she gently closed her legs and said that she needed a little break. Apparently she just meant a break from her own pleasure, and not from sex in general, because it took her all of five seconds to readjust herself into a kneeling position and she suddenly had Charlie’s huge erection in her mouth.

I was momentarily neglected, although I didn’t mind, I was so enjoying watching Charlie’s beautiful member with Jessica’s beautiful lips around it. I reached down and stroked my own pussy with one hand while squeezing my nipples with the other. My fingers felt amazing as they stroked my clit seemingly with a mind of their own, yet I was not anywhere close to nearing orgasm, I knew I needed some help with that. As if reading my mind, Jessica reached her hand down and began to knead my pussy with her long and able fingers. Charlie pulled out of her mouth to hold off on his orgasm and looked down at Jessica’s hand. He moaned at the sight of my pussy being worked on by another woman and asked Jessica if she’d ever gone down on another woman before.

Jessica responded that she hadn’t and Charlie gently asked if she’d let him show her how. She agreed enthusiastically and he helped me reposition myself on the bed. He dove between my legs first and, between licks and sucks, explained to her what he was doing and what I liked. She asked him if he would let her try, and she dove in triumphantly. Her tongue was strong and probing, her lips firm but tender. It took me only a minute or two to work up to my orgasm, and as I was about to come, she shoved two fingers into my pussy, intensifying and prolonging my orgasm. It was incredible.

Charlie’s erection was throbbing so hard from watching us that it almost looked painful, and he quickly maneuvred us around so Jessica was sitting backwards on his lap. He told her that she was about to have one of the strongest orgasms she’d ever had in her life, and deftly lifted her up and slipped his penis into her dripping hole. I was facing the whole scene and knew instinctively what Charlie wanted me to do.

As she slid up and down on his penis, I leaned forward and began to suck her clit again. Charlie had to firmly hold her hips to prevent her from falling over, she was shaking so violently from the multiple sensation…. yet somehow she wanted more. She pulled his penis out of her pussy and began to slip it into her ass. She finally got him in all the way, and I resumed my licking. She wanted something more, though, and she said “Top drawer…. please look in my top drawer!”

I reached into the top drawer of her bedstand and saw a plethora of vibrators and dildoes. I selected a small bullet-style vibrator and turned it on. I slipped it up into her pussy and resumed eating her. Charlie began to moan; he could clearly feel the vibrations through the walls of her pussy. Jessica was so beyond ecstacy that she wasn’t even moving anymore, her eyes were rolled up into her head. Suddenly, out of nowhere, her entire body tensed up, and she screamed at full volume as she came. The bullet vibrator shot out of her pussy as the muscles convulsed, and a stream of liquid poured out, too. Charlie began to pound into her tight anus as he came inside her, and the pressure caused her to climax again, only seconds after the initial orgasm.

“Charlie, that first time she came, she squirted,” I told him. He looked at her adoringly and told her how it had taken me years to learn how to ejaculate. She told us that she often does when there’s combined pressure in her ass and pussy. We were both enamored. I almost totally forgot that this was the same roommate that always gave me hell about bringing boyfriends around.

She continued to describe how she really liked to use a double dildo to fill both of her holes at once, and I got an idea. I reached back into the drawer and immediately found what I assumed was that very dildo that she had just mentioned. It was extremely large, I was amazed that she could truly fit both ends into her at once. She clearly knew what I was thinking, because she took one end as I took the other, and we slipped them into our pussies right to the hilt, so our clits could touch if we worked it at the right angle.

We began to buck and grind against each other. Charlie’s erection began to perk up again, but he ignored it and reached down and squeezed both of our nipples. This position was awkward for us, but we still managed to work ourselves into a frenzy, resulting in yet another orgasm for both Jessica and me.

I was getting toward satiated, I only wanted one more thing…. Charlie’s cock buried deep inside me. I positioned myself over Jessica on my hands and knees, her pussy directly under my face and mine directly over hers. Charlie began to take me from behind as we both ate each others’ pussies. The final orgasm actually took the longest to build up for all three of us, and when it finally came, the most intense. I felt Jessica’s lips on my pussy, tasting my juices mixing with Charlie’s as they dripped out together. I reached around and stuck one finger in Jessica’s anus and one in her pussy as she came, and I was successful in making her ejaculate again. We all collapsed, exhausted, and curled up together on the bed.

I giggled as I told Jessica that I couldn’t believe she went along with it. She and Charlie began to giggle, and she confessed that she’d known all along about the plan, since he had told her last week. Apparently she had confessed to him that the reason she was so angry that I always had sex in the other room was that she was just jealous that she didn’t get invited. I promised her that I would never make that mistake again.

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