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Chicago Adult Dating Story
Theme: Gay & Lesbian
WHAT ARE ROOMMATES FOR?When I was in college, I shared a large four-bedroom house with two other men and a woman. I answered a "roommate wanted" ad on the campus bulletin board and arranged an interview with my prospective roommates. Ted and Frank were two nice-looking, well-groomed city boys and Carol, although not beautiful, was cute and sexy. Their roommate had moved out recently and they needed a replacement for the empty bedroom. I liked them immediately and they seemed to like me. I agreed to their terms, paid my security deposit and rent, and told them that I would move in the following day.
The next morning, I loaded my meager possessions into my car and drove to my new home. As luck would have it, my engine began to overheat and I was forced to pull into a service station. The mechanic told me the fan belt had broken. He was very busy but promised to get to it as soon as he could. Rather than wait for what could have been hours, I decided to walk to my new home and take a nap.
The others weren't there so I assumed that they were attending class. I went to my room and stretched out on the bed. I slept for awhile and awoke to voices coming from downstairs. When I walked out onto the second level and looked down into the livingroom, I got the shock of my life. My new roommates were having sex on the couch. They apparently didn't realize that I was there because my car was not in the driveway.
Frank was sitting on the couch with Carol on her knees sucking his cock. Ted stood beside the couch with his cock in Frank's mouth. I had never seen anyone having sex, not even in porno, so I was fascinated by what they were doing. I quickly stepped back out of sight and watched from the door of my room. I was naïve and innocent. The only sex that I had had was an occasional hand job from my prudish girlfriend. I was particularly interested in what Ted and Frank were doing. I knew that most men were straight and a few were gay, but I didn't know that there was a third category in between.
Carol said something and the two men switched places. Ted sucked Frank's cock just as enthusiastically as Frank had sucked his. Watching them gave me a powerful hard-on. I took out my nine-inch cock and began to masturbate. Carol took Ted's cock out of her mouth and said that she wanted to fuck. Ted and Frank tossed a coin to decide something. I soon found out what it was. Ted mounted Carol and she immediately grabbed his cock and stuffed it into her pussy. Then Frank mounted them and worked his cock up Ted's ass. I didn't know at the time that they were performing one of the most popular bisexual acts - the man sandwich.
Once they were hooked up, they really went to it. Each time Ted pulled out of Carol, Frank thrust forward to drive his cock deep into Ted's ass. Carol's face was toward me so I could clearly see the stages of arousal that she was experiencing. First, there was a big smile and a look of deep satisfaction. The smile was gradually replaced by a frown and a look of intense concentration. Finally, her face contorted with lust and she shrieked that she was cumming. Ted and Frank laughed when she nearly bucked them off. "Keep her cumming!" Frank said. Ted had a big grin on his face as he continued pumping Carol's pussy. I had never made a woman cum so I didn't realize how good it feels. Carol's orgasm seemed to die down and then start up again. Finally, the smiles on the men's faces disappeared. They convulsed simultaneously as Ted shot his load into Carol while taking Frank's load in his ass. Watching them cum caused me to lose control and I came in my hand.
They lay in a limp pile for quite a long time before Carol told them to get off of her. "That was a good one," Carol said, as she kissed them on their cheeks. "You guys really know how to use your pricks." How I envied those two!
When my roommates left the livingroom, I slipped out of the house without being seen. After calling the auto shop and learning that my car was ready, I picked it up and returned to the house. My new roommates were dressed and watching TV in the livingroom. As they helped me move my possessions into the house, I felt sure that my deception had been successful.
As the weeks passed, I adjusted to my new surroundings and began to feel at home. I liked my roommates and got along with all three of them. Carol was a tease who liked to walk around wearing only a towel around her hips. She had a beautiful pair of tits. Every time I saw them I got a raging hard-on. I kept hoping that I would get another sex show, but it didn't happen. They were having their parties behind the closed doors of their rooms. I wanted to join in but was too shy to ask if I could.
My roommates often went out together on weekends to party. I felt very left out when they didn't invite me to go with them. After a month or so, they finally asked me if I wanted to join them. I was elated and gladly accepted. We went to their favorite honky-tonk and began drinking. We made small talk for awhile, then they got down to business.
Carol squeezed my thigh and said, "The boys and I have a little arrangement." She moved her hand higher and squeezed my cock. "We take care of each other's needs, if you know what I mean." Frank and Ted were grinning like possums. "We know that you saw us your first day in the house, and because you didn't try to join in, we assumed that you weren't interested. Is that how it is?" I don't remember how I answered, but I must have made my point because an hour later I was naked on Carol's bed having the time of my life.
Carol was between my legs while Frank and Ted were to each side. They passed my cock around and took turns sucking on it. "If we had known you had such a big cock, we would have seduced you sooner," Carol said. "Yeah, it's a shame that this beauty has been going to waste all this time," Ted added. What they were doing to me felt better than anything that I had experienced in my young life.
I knew that if they kept it up, I was going to cum. I was so naïve that I didn't know what I was supposed to do with the stuff. They laughed when I asked them about it. "Just let it fly," Carol said. "That's the best part. We'll take care of everything." No sooner were the words out of her mouth than I began to shoot. Cum went flying everywhere. They tilted their heads back, opened their mouths wide, and stuck out their tongues to catch my jism as it fell like rain. They managed to catch about half and the rest landed on their faces.
Ted briskly pumped my cock with his hand. "Come on, baby, get on it before it goes soft," he said. Carol straddled me and lowered herself onto my twitching cock as Ted guided it into her pussy. A man never forgets his first pussy. It always feels so much better than he had imagined in his wildest dreams. It's never quite as good after that first time. Carol's cunt was tight, hot and slick. It swallowed up most of my cock. She posted up and down on me to keep me hard. It worked!
While Carol was giving me my first fuck, Frank and Ted licked my balls and the two or three inches of shaft that wouldn't fit inside Carol. One of them put the icing on the cake when he slid a finger up my ass. I had Carol all to myself for awhile. Then she shouted back over her shoulder, "Fill my empty holes." Frank got above us and worked his cock up her ass. I could feel the heat from his cock radiating through the thin membrane separating the two holes. As he fucked her hard, his balls bounced off of mine. Ted filled her other empty hole - her mouth. Our cluster-fuck was complete.
Carol pulled Ted's plump cock out of her mouth and offered it to me. I wasn't ready for that and declined her offer. It would be several months before I tried that. We didn't all cum together but we were very close. I lasted the longest because I had already cum once. As I shot my first load into a pussy, one of the guys gently squeezed my balls to encourage the cum to flow.
It was two days before we partied again. Carol said that she liked to watch guys jack off and that I would have to do it for her before she would allow me to join in. While Ted sucked her tits and Frank licked her pussy, I stood at the foot of the bed and masturbated for her amusement. I was embarrassed at first, but gradually began to enjoy it. When I asked her if I could join the party, she said, "Not until you cum. I'll let you do it on my tits." I jerked my cock harder and faster and soon unloaded all over her sweet tits. As soon as I was finished, Ted and Frank licked up every drop. The party that followed was very much like the one that I have already described.
We had a sex party every couple of days. Carol always took it in the ass from Ted, Frank, or both of them. I was eager to see how that felt, but when I asked her if I could poke her butt, she told me that I would have to do it to Ted and Frank first. I refused at first, but they eventually talked me into it. The boys flipped a coin to see who would go first and Ted won. He wasn't sure that he could take my big cock, and insisted on applying the lubricant himself. He carefully rubbed hand lotion into every inch of my cock.
Ted went to all fours and stuck his ass up in the air. That's when I noticed that his ass was just as nice as Carol's. From that angle, he could have passed for a girl. Frank and Carol knelt on both sides and held his butt cheeks open for me. I penetrated at least six times and each time he pulled away. On my seventh attempt, I started to cum before I could get it in. "PUT IT IN OR IT WON'T COUNT!" Carol shouted. They held him while I pushed my spurting cock up his tight ass. I managed to get it all the way in before my orgasm ended. It was the most powerful orgasm that I had ever had.
I masturbated as I watched them have a threesome. When I had a fresh hard-on, I told them that I was ready for Frank. He took my cock in a different way. Carol and Ted held it straight up as he straddled me and impaled himself on it. He groaned and gritted his teeth, but took me on the first try. While he slid up and down on my shaft, Carol lowered her pussy to my mouth. Before long, Ted jacked Frank off all over my chest and belly. After he came, Frank had no desire for my cock up his ass. Ted said he wanted to try again and took his place. Our second attempt was a success, and I soon had every inch of cock up his tight ass.
Carol was a bossy bitch who often took charge of our mini-orgies. One day she was especially cranky about Frank's sloppy housekeeping. She took him across her lap and spanked his bare ass until tears welled up in his eyes. Ted begged for the same treatment, so she did him, too. While she was beating his ass, he emptied his load on her bare thighs. Watching my friends getting spanked made me extremely horny. When Carol saw me masturbating, she ordered me across her lap. I managed to take a dozen smacks before the burning sensation became too much to bear. We were all exceptionally horny after the spanking and began fucking like animals.
Each time we fucked, they tried to goad me into becoming fully bisexual. I enjoyed having my cock sucked by my buddies. They were actually better at it than Carol was. I also loved fucking their tight asses. Carol was especially insistent that I go the whole route. She was a control freak who got a big rush out of coercing men to do her bidding. One day as we were getting ready to fuck, she told me that they were going to cut me off if I didn't suck and take it in the ass.
I couldn't bear the thought of not having sex with them. By then, I was addicted to it. After I reluctantly agreed, Carol told me that I could choose which cock would go up my ass. Frank's cock was a little thinner than Ted's so I decided that he would be easier to take. I greased him very carefully with Vaseline then went to all fours and stuck my ass up. Even though I was frightened, I was also very excited by the erotic adventure that I was embarking on.
Ted shoved his sleek cock into my mouth. My first impression was that it seemed so natural to be sucking a peter. It fit my mouth perfectly. Then I noticed the heat radiating from the bulbous head. A fever seemed to be raging there. Frank penetrated my anus very slowly. It didn't hurt as much as I expected it to. My anus soon adjusted to the size of Frank's cock and as the nerves were stimulated my pleasure intensified.
Carol sat on my back and slapped my ass hard. "I love the way his butt tightens up when you smack him," Frank said. After a dozen vigorous slaps, Carol slid forward until her cool ass cheeks pressed down against my inflamed cheeks and peed down the crack of my ass. The warm fluid flowing around Frank's cock triggered his orgasm. He growled like a dog as he blew his load up my ass.
While Frank was shooting cum up my ass, Ted let his load go in my mouth. There was a lot of cum, but I managed to hold it all. I had always imagined that cum tasted terrible, so I was pleasantly surprised to discover that it had virtually no taste at all. When he finished spurting and pulled away, I was able to swallow his essence in three or four hard swallows. When I confessed to them that I had enjoyed the experience, Carol said, "You're officially bisexual, then."
After a rest, I told them that I wanted a repeat with the boys switching places. While I doggy-fucked Carol, Ted reamed my ass and Frank fucked my face. We had a fabulous time after that. There were many possible combinations to try. When Ted got a steady girlfriend and persuaded her to join in our parties, I was in paradise. I'll tell you about how we initiated her some other time.
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