Robin was lost in thought as she rode the Clark St. bus on her way to her job as a junior trader at the Board of Trade in downtown Chicago. Having only graduated from the U of I three months ago, she felt very lucky indeed to have landed such a good job in such a short period of time. If she kept her nose to the grindstone and worked hard, Robin was sure that not only would this job provide the mental challenge she needed, but also the kind of money most folks only dreamed of. As the bus swayed to and fro as it passed over the Chicago River bridge, Robin thought that the only real problem she ... Continue»
About six years ago I was in university and living on campus during the summer along with a few other guys, including a guy I roomed with off campus during the school year. Jeff and I were in the same program and we were taking summer classes while working for our department. He and I were fairly big geeks and only occasionally would we do social things like going to the bars to drink and socialize with friends.
There were several women also living in residence then, including one attractive woman named Kathy. She was a tall, curvaceous brunette in a related program. Some of her and our classes overlapped so we frequently saw and studied with her. One night when all of us were out at the bars, Kathy and a very d***k Jeff went back to residence together a bit early and seemed to disappear. Neither one said much about it during the next few days but within a week the two were dating to the amazement of everyone. Kathy had guys hitting on her that everyone, including Jeff, agreed had funnier personalities, better looks, and some of them had money to burn on a woman like her.
About a month after they started dating the summer came to an end so Jeff and I moved into an off campus apartment for the school year. I was a bit surprised when Kathy moved permanently into Jeff's room almost right away, but that was fine with me since we were all friends.
The teasing started soon after. Kathy would seemingly wait until I was walking down the hallway and then dash behind me from the bathroom to their bedroom, giving me quick glimpses of her wrapped in a towel way too small for a body with curves like hers.
Frequently she would come to breakfast without Jeff in a loosely belted robe, which would swing away from her body as she moved. I grew very familiar with how soft, and stroke-able her upper thighs seemed to be, and how her breasts filled the robe and hung so nicely when she bent forward to put something on the table. The looks she gave me during all this made it seem like she was interested, but she clearly wanted Jeff.
Over two months this grew increasingly common, with things added in like their door always being open while they made out on the bed. I quickly began to be used to catching a view out of the side of my vision of Kathy in some damn hot underwear on top of Jeff when I went to my empty bed at night.
Kathy's old roommate, an incredibly hot blonde named Rachel soon began to show up at our apartment at all hours. It was not unusual after a while to see her there in the evening when I went to sl**p and again the next morning when I woke up. I grew very interested in her but still fantasized about about Kathy sometimes. Rachel had a beautiful face, a warm and outgoing personality and a body to die for.
One night I wasn't sl**ping very well, possibly from the muffled noises were waking me up so I got up for a drink of water. Their door was closed as I walked to the kitchen, but I heard a door open and close while I was drinking the water. As I walked back to my room it was possible to see that the bathroom door was now closed which I assume meant that Jeff's door was the one that opened. The bathroom was the first door in a hallway, and the only one visible before you turned left into the hallway. I walked around the corner and could see that Jeff's door was open. I was expecting the usual peek of Kathy making out with Jeff so I stopped in my tracks when what was going on actually reached my brain.
You know how some things just grip your attention? Like a three car pileup on the freeway, or someone with a nice ass bent over to tie their shoes on the sidewalk in front of you? Well this was like that, all I could say was 'Fuck!' and just stand there and stare.
Jeff was on his hands and knees facing the end of his bed, almost opposite of me was Kathy who was behind him wearing a strap-on. Kathy was in the process of slowly drawing the dildo about five inches out of his ass over two seconds then fucking into him again very hard. She repeated this two, three, four times then changed her tempo to a faster one. Pulling it out fast and watching how the flesh of his asshole would pull out a bit not wanting to lose the dildo fucking it so hard, then slam it back after a half second pause. During one stroke she misjudged how much cock she had and pulled it all out so I had time to look at it in full. It was a kind of pink jelly dildo of about six or seven inches with a thickness of around an inch and a half or more.
I think they must have noticed me standing there staring but they did not look over or really show any indication other than Kathy seemed to be performing a bit for an audience in the way she was riding him. She had taken both her hands off his waist and put the right one the small of his back, while the left one she put on her own hip. Watching sweat pour off all those curves I was seeing for the first time while she was kneeling behind my roommate fucking him hard and in a relaxed commanding position was so fucking amazing!
My cock inside my jogging shorts was rock hard in just a few seconds. After a minute of watching this I didn't care about anything, I needed to see this. And I definitely needed to do something about my cock it was feeling full and ready. Pulling the ripped shirt I had thrown on out of my shorts I put my right hand under the shirt where the head of my cock was had made it above the waistband of the short. I put my thumb and forefinger around the head and my other fingers around the shaft and started to rub the head and caress the shaft. This was hidden by the shirt which reached down to about my balls if they had bothered to look over, but I wasn't really worried about that. I just wanted to pay attention quickly to my cock while I watched this incredible scene playing out in front of me.
This went on for minutes and I needed more, saying the hell with any kind of propriety I just yanked off my shirt, tossed it towards my open doorway with my shorts following less than a few seconds later. Have you ever stood nude in your roommates door and masturbated in clear view while they were fucking? While they were being fucked in the ass by a hot brunette with big tits and a seven inch strap-on buckled around her small waist? It was unreal and incredibly hot to be doing this.
About a minute after that I heard the toilet flush behind me and the tap run in the bathroom for a few seconds. The angled way I was standing in Jeff's doorway left that part of the hallway behind me. I had been using the door frame to lean my left shoulder against while my left hand reached down to pull on my balls and give soft strokes to the sensitive spots underneath, while my right arm was free to fly all over the place as it yanked on my cock.
The bathroom door opened and I tried to make myself turn around to see who was there though I almost instantly guessed it must be Rachel. I only heard one soft footstep scuff the carpet before she reached me. I guess she wasn't mad about me watching because she didn't say anything. I stopped my right arm and just let that hand massage my cock as she stopped behind me. I could feel a breast touching my right shoulder as her head and some of her right breast peek around that side to look in the doorway at the two lovers, then at my cock and finally up at me.
There was no way she could not have realised how turned on this whole thing made me and I guess that's what made her pull her torso back behind me again then reach up and pull on my shoulder a bit to turn me around. I didn't want to turn away from the view but what seemed like a nude blonde was trying to get my attention and that's hard to ignore too.
I turned around and there she stood. Five feet eight, with a truly beautiful face that was only slightly below my face. Her breasts were nicely firm C cups that had perky nipples standing out at me. What caught my attention though was the strap-on fitted around her waist and the blue jelly dildo sticking eight inches out of it. She had it held in her left hand so that it pointed up between her breasts, I guess so that it wouldn't hit my ass while she looked around me a few moments ago but she let it go when I was fully turned and staring at her cock. It flexed itself and arced down, on its way it brushed my balls in a quick tap that I definitely felt. I looked up to see her eyes less than a foot from mine. Her dark green eyes mesmerized me and the smile on her face made it clear that she was happy to see me.
She said, "Hi Mark, it looks like you want to join the party."
All I could do was manage a jerky nod in response, but that seemed to be enough. She stepped forward while putting her hands up behind my head and neck and drew my willing face down to kiss her. Her strap-on's dildo slid between my legs with my balls resting on the long shaft. The dildo's movement forward rubbed them in a very nice way. The shaft seemed to be greased and just pushed open my upper thighs until its head poked out behind me. Her entire body was rubbing me and the feeling of her breasts pressed into the bottom of my rib cage was very nice after being single for so long. The kiss seemed to last forever as we massaged each others lips.
After a while I felt her mouth open and her tongue poke my lips, there was no way I would deny it entrance and it slipped inside me. She played with my tongue for a bit but then I realised just how long that tongue was when she gave a few light flicks to the top of my mouth right in the sensitive spots behind the upper teeth. A few of those made my mouth feel very tingly though I think most of that was in my head. She must have felt the jerks my cock was giving through her stomach and realised how she was affecting me. She pulled her tongue back and I was just about to wonder what was wrong when she thrust it back in. That tongue was amazing! It felt like she almost flicked my tonsils in the first thrust, but then she drew it back and thrust again and I knew what the difference between almost touching it, and truely touching it. I felt like I might need to gag a bit as she began fucking my mouth with it. I could hear Jeff's moans overtop the ones I was starting to make as we both were fucked by women if only for now in different ways.
During all this I knew what it was likely to lead to as soon as my mind had grasped what Rachel was wearing around her waist and she seemed to know instinctively that I was ready and waiting for this. I had never even put a finger up my ass much less anything like her cock, but I could tell Jeff seemed to love it and I doubt I could have resisted anything Rachel wanted in the state I was in.
She pulled back her head a bit and when my eyes opened she looked into them and said, "Do you want me to fuck you like I did Jeff, and Kathy is doing right now?"
"Yes, please", was all I could gasp. If you had asked me an hour ago if I would agree to this I would have just stared in shock, but now I wanted it, oh how I wanted it! Nothing in my life had prepared me for this. A few porn movies and magazines that had lesbians fucking each other did not prepare a person for a night like this.
She stepped back, which pulled the dildo from between my thighes and said, "Turn around and watch them a bit."
When I was fully turned and staring at them, I could see Jeff and Kathy were now flicking their eyes to me occasionally, but they were still mainly caught up in what they were doing. They looked at my face and my rock hard cock but I didn't have any shame. How could I when what they were doing was so over the top it had removed any inhibitions from my mind.
As I stood there I felt Rachel kiss the nap of my neck and slowly she licked and kissed her way down my spine until it reached the base. In my minds eye I tried to picture her kneeling behind me but that was hard to do with my eyes open and staring at where Kathy's dildo was sliding deeply in then out of Jeff. She grabbed both my ass cheeks in a firm but not harsh grip and pulled them to the side. Instinctively I relaxed my ass muscles so they did not fight her and slide my feet a bit farther apart. One hand went up to the opposite side of the door frame and my left shoulder went back to resting against its side of the frame.
I felt her incredible tongue again but this time its tip flicked the ring of my asshole in a few quick taps that set it to tingling. Instead of keeping that up though she extended it and I felt it lap the bottom of my nuts as she dragged in from them along the muscle there back to my ass. That soft wet feeling was just what I needed. She went back to flicking my asshole, again and again. Soon it was wet and I guess she felt it was ready since she reached up with an index finger from one of the hands holding my cheeks and probed a bit before it slipped quickly in to the first knuckle. I could feel someone in my ass for the first time in my life and I liked it. There was no pain, only the tingling I still felt reverberating from when she was licking me.
She drew it out entirely, then slid it back in and then repeated that a few time. She did not go very deep, just that first knuckle. I felt it withdraw and then she was licking me again, it wasn't right on my asshole, but around it and along the crack. I desperately wanted her tongue on my hole again. Actually I wanted her in my hole again too, to fuck me with that finger or her dildo, but she was teasing me a bit before making me hers entirely.
Her finger came back soon enough though and she started to thrust it in this time. It quickly sank to the second knuckle after two strokes. A few more strokes and I could feel the base of her palm right beside my asshole. She pulled the index finger out but this time she did not pause to give me some of that tongue I already loved. This time she put her left hand between my cheeks and used spanning it open she held them apart while she slide both her middle and index fingers into me. They did not go far, but she kept at it, forcing them deeper and deeper into me to prepare the way. There was a bit of discomfort but that quickly fled as my ass relaxed. I think all the hormones rushing through me helped take away any pain almost as soon as I felt it. Within another minute I had both fingers all the way in me.
I was still watching Jeff and Kathy going at it, they must have been fucking for at least ten minutes now as I watched them. I had no clue how long she had been slamming it into him before I saw them, or how long Rachel had done it to him before that. He leaned back and rose off his hands so he was kneeling only slightly bent over and she leaned back so that nice ass of hers rested on her heels. It was almost like she was sitting and he was bouncing on her lap in a chair. I had seen women bouncing in a reversed position like that on a guys lap but never a guy fucking himself up and down on a woman in this way. His hard cock made it clear he was not a woman, and the stream of white running down it that I could now see and the pool on the sheets that he no longer covered made it clear he loved this. I guessed it must be rubbing his prostrate to give him that hardon.
Behind me Rachel, I guess, had decided she wanted to make sure I could take her and was now putting three fingers in a kind of triangle into the ring. My ring slowly accepted them but it took longer since while the tips were pressed close together the bases of the fingers could not be and what was an inch or less wide at the tip was almost two inches at the base. But she continued to fuck me with them until she had one, then two knuckles in. I think she went a bit deeper than that but she soon stopped entirely. Withdrawing her fingers slowly I felt like my insides were being pulled out, my ring gripped her tips only lightly though since it was stretched nicely.
"Do you still want it?", I heard behind me, "If so, just kneel down on your hands and knees in the doorway."
I knew I needed this and there was no way I could walk away without regretting all my life having given up this chance to be taken in the ass by such a beautiful woman. I dropped to my knees and then placed my hands on the floor. I let my head drop down so I could look back and I saw her lower body as she moved up behind me. Her blue cock almost touched the floor with its realistic tip. She reached down with her right hand and grabbed that tip and took it up out of my view. I looked up at the bed and could see that Jeff had dropped down to his knees again and Kathy risen up off her heels to fuck him in the exact position I was in. They were both twisting their heads, looking at Rachel and I, though they couldn't see my ass and her strap-on the way I could see the two of them because of the angles.
Rachel rubbed the head of her cock up and down my crack a few times, once tapping it lightly against my balls. But she was too hot to tease me for long. I think the prospect of fucking a new guy was just as hot for her as this had turned into for me. She placed the head against me hole and slowly fed me her dick.
I could feel my ring stretching wide as she managed to get it into me almost immediately. About three quarters of an inch of the head went in, but that was most of the thickness. Pulling the head back with her hand she quickly pushed it back in when just the tip was left. This time the entire head and about an inch of the shaft made it in with no problem. I think she could have slammed it in for several inches, but she was more considerate than that since I was a virgin to this. She pulled it out and then she started to fuck me for real. She fucked it in and she pulled it back only to push it firmly. She wasn't going fast but she was fucking me and going deeper with every stroke until she had about six of the eight inches in me. I don't know why but that was about all I could take right then.
She must have looked so hot doing that, I wished I could have seen her breasts jiggling and face smiling, perhaps there was a bit of a grimace instead as she concentrated on doing me. I could only imagine what it looked like at that point. I tried picturing her face on Kathy up in front of me but that only partly worked.
I could feel the dildo inside me rubbing something that I later learned was my prostrate and it was very nice. I felt full when she pushed into me and an aching void when she pulled herself out of me. I knew then that I wanted to be with her as long as she would let me, I did not want that emotional void inside me that would be there if this night was all of her I ever had and I did not want the physical void when she pulled that beautiful cock of hers out of me.
She was moaning behind me and I was starting to give little grunts from her thrusts. This went on for long, luscious minutes before I felt her all of a sudden stop and groan deeply behind me. I could feel small shudders through the dildo as it was shook inside me. The pause was about twenty seconds then I felt her pull the dildo out. I looked over my shoulder to try and find out what had gone wrong and saw her smiling face.
She slapped my ass and said, "Roll over!"
Swiftly my back was pressed against the carpet, with her kneeling between my legs. She did not say a word, just started to feed the dildo back into me. One of her hands gave a short stroke to my dick and then she was in me again. During those short seconds she was out of me I could feel myself needing her back and now she was. After only a few strokes though she had decided my thighs would not open quite the way she wanted. She reached out and grabbed my calves and pulled on them a bit but I guess she did not quite have the leverage. But I had been watching her face and realised what she wanted. I put my ankles up over her shoulders. Now my ass was a few inches off the ground and she fucking straight into me. My cock was still rock hard and pulsing from all this, the short pause had not affected it in any way.