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Sweet dare


Varsity reunion with Tracy and Cara
20 years after finishing university, my group of classmates got together for a reunion. I was one of only 4 guys in my class and there were about 35 girls. Not that more than about 5 of them were hot, but that's besides the point. All through my 3 years at university I hung out with a group of 4 girls. Two were ok, one was hot, the other was ... not. But 20 years later, the hot one was not that great, the two ok ones were smoking hot, and the other was ok.
So about 20 of us met up again 20 years after graduating, at a local restaurant one evening. There was a bit of joking around and a few sexual innuendos thrown around but no real misbehavior. that was a pity as some of the really hot girls from the class were there.
When everyone decided to head home my 4 friends and I were not done catching up, and Cara suggested going to her place for a few more drinks. Now Cara was not the hot one in university, but as she she had aged into something of a milf. I guess she had developed a lot of confidence in herself that some of the others hadn't. It ended up being Cara, her best friend Tracy and I who went back for drinks. Cara was wearing a burgundy evening dress with no back and obviously no bra, and Tracy was wearing a short black form-fitting dress. Of course I expected a bit of misbehavior but was not expecting any sex.

Tracy was petite, a good figure, very nice ass and small perky boobs. I had had a few fantasies about her during university but she always had a steady boyfriend so that was not to be.
Cara was very pretty. She had a pretty face and a perfect classic figure, like something out of an art museum. I had always had a fantasy about her posing for life drawing but that was not to be either - she did not have the confidence back in university. She had about a B cup boobs, nicely shaped. She had been through a string of boyfriends and there was always a suspicion among our group that her and I would get together at some point, but I guess I also didn't have the confidence back then.

So anyway of course I was hard all the way to Cara's place thinking about all this. This got me into a mood for instigating a bit of trouble.
Once we were there, we chatted for a long time about life over the last 20 years. Tracy was happily married, but Cara had been through a divorce about a year before and was still single. She was asking Tracy what the secret was. Tracy was saying that it was about not boxing each other in, and respecting each other. It took Cara a while to figure she was talking about not boxing each other in sexually, and Tracy was not quite ready to say it, but after a bit of prodding and a few more drinks, it came out that she let her husband sleep with whoever he wanted, as long as he always came home to her. Cara was lamenting that she had always found men to be such jerks, to use her and then forget her. This is where I thought the evening would end. I downed the rest of my drink, looked Cara in the eye and said it was a shame men treated her like that, that I had always thought she was beautiful, inside and out, and that she should not define herself by the jerks around her.
It came out a bit serious, but was a real compliment, but little did I know that I thought was the end of the evening made her sopping wet.

We all got up and had another drink from the counter, and I was complimenting Cara on what a nice place she had - and she said, I haven't even given you the tour! she showed me around the house room by room while Tracy went to freshen up. She showed me her bedroom, and I caught her eye in the mirror as we were about to walk out. She paused, and gave me the puppy dog eyes. I looked straight at her, and I said, " I mean it, don't let people treat you like dirt". She hugged me tight, and at that moment Tracy came in, and Cara and I didn't know where to look, dropping our arms off each other. Tracy joked, "can't leave you two alone I see. finally, after 20 years you guys are getting with the program."

Cara and I didn't know where to look, but Tracy kept encouraging us: "What you said to her was really special - If only there were more guys like you." Cara sat on the edge of the bed, holding my hand. I could feel my cock pressing on the front of my pants. I was facing Tracy, but Cara facing her diagonally across me - so my cock must have been right in her line of sight. Tracy and I sat down on either side of Cara, and we were all in a kind of loose group hug, and i was caressing Cara's back before I even realized it. I only realized when my hand bumped into Tracy's hand, doing the same thing. we sat there for a while and then Cara got up and said she wanted to get changed. Tracy were about to excuse ourselves as Cara would obviously get changed in her room, and she said, no, stay, I know you both love me and respect me, I don't mind if you see me naked. she slipped the shoulders off her dress and it dropped to the floor. I had a nice view of some side-boob, and the frontal view of her boobs in the mirror. She was wearing a black v string kind of thong.
I complimented her on how good she looked and said that it was difficult not to stare. She turned around and walked right up to me, her nipples almost touching my cheeks, cupped my cheeks in her hands and said, you can stare as much as you like. Tracy said, now Cara's got all the attention, and I said to her, "because you have all the clothes." She replied, "you do to. Let's all take them off." This was better than I had hoped for, and I still did not think it would go further than that, so I was very self conscious about my huge erection as I started undressing. While I was unbuttoning my shirt, Cara bent over right in front of me and took her panties off, giving us a nice close up view of her pussy. She had a neat little strip of fur, but her mound was smooth.
Cara bent down to untie my shoelaces, brushing her face very slightly on my crotch, with my cock nearly bursting through. I kicked my shoes and socks off and undid my pants and slid them off. I paused before removing my shorts. Tracy took that as her cue to undress. She stood in front of the mirror and peeled the dress up, revealing that she had absolutely nothing on underneath. That was what she had done when she went to freshen up. Then she knelt down with Cara and they both gently slid their hands into the back of my shorts and peeled them down. Their faces were only inches away from my cock, which sprang out between their faces. Now I do have a nice one, but until then I had never realized how nice - I thought I was average, but since then I have been told that I am well above average. The looks on their faces were quite something - clearly they thought it was huge. They gave me many compliments on it. We stood and sat around for a while, looking in the mirror, me in the middle and laughing about the unexpected situation, and also exchanging compliments about each others' bodies. Clearly with all the encouragement we all started to get really horny. After a while, Tracy said she wanted to have a closer look at me again, and I lay on the edge of the bed and she knelt down to look. Still at this point I thought that was as far as the evening would go - some eye candy and a new level of friendship, but I did not expect anything more.
I was staring at the ceiling while Tracy was inspecting my package, and Cara had joined her. Very lightly at first, they both started to touch and tickle. when I looked down, the two girls were looking up at me, and started to kiss the sides of my cock. At this point I realized that there would be something like in a porn movie happening.
They leaned forward, rubbing their tits over me, kissing and caressing. Tracy went back down, and Cara climbed onto the bed next to me and I reached over and grabbed her tits. she leaned in and kissed me passionately, while Tracy was licking my balls and the underside of my balls. Cara then turned around while still kissing me, and then started crawling over me, kissing as she went, letting me suck her nipples, which were already standing up before I started. she kept moving down, and Tracy did too. Cara put the tip of my cock in her mouth and started sucking it, at the same time as Tracy's tongue started going lower and lower. Cara moved down and gave me a face full of her pussy just as Tracy's tongue found my asshole. Well I put all of that thrill into the attention I was giving Cara's pussy. I nibbled on her lips, and as she opened up I put my whole mouth over her clit and sucked hard. she moaned repeatedly and started thrusting her hips over my face. IT just about wore my lips off but she was already shaking with orgasm. she stopped sucking and threw her head back in pleasure. Tracy said she wanted a turn. So Cara moved down, and sat over my cock, facing Tracy, who sat with her ass over my face. I knew what she wanted, which was something I'd always wanted to do to a girl. I kissed her asshole and went round and round in circles with the tip of my tongue. then I licked the area between her asshole and her pussy and when she was ready she lowered her pussy closer to me.
I am always amazed at how different different women's pussies are. Cara's clit and inner lips were small, and Tracy's lips were long and her clit was much bigger - it stood out like a little cigar wrapped up. and i held her lips open with my fingers, rubbing them between my thumbs and forefingers, while knocking her clit from side to side with my mouth and nose as hard as i could.
I kept looking to the side, enjoying watching another kind of exploration happening, the girls first held hands and then held each others' tits as Cara started riding my cock. It felt so good I wanted her to keep going till I came, but of course I wanted to have a go at Tracy's pussy before that happened. Then the girls started kissing each other - I don't think either of them considered themselves bisexual but they just enjoyed the kissing and fondling. Finally when I was about to cum, I pushed my knees up to stop Cara thrusting, and both girls climbed off. I told Tracy I wanted her pussy. She said sure, just don't cum just yet. She knelt on all fours and Cara sat back and watched as I thrust in and out very slowly. Her clit was a lot bigger and her lips a lot longer, but wow her pussy was tight. I had to spit on my fingers to lube up more, just to get the tip in. I prodded around with the tip for a while, till the lube had spread, then i still only gave her the head, till she was begging for it. I went slowly slowly, then suddenly all at once, all the way in. She screamed so loud I bet the whole neighborhood heard.
Then I repeated the process, starting with the half-thrusts, then building up to a few full thrusts, then I had to stop or else I would cum.
Tracy rolled onto her back and I fingered her with two fingers in her pussy, pulling up and down hard, while holding her clit still with my thumb. she came hard, her whole body trembling. she even squirted a tiny bit.
Then Cara knelt next to her, and Tracy took a turn to watch. I thrust hard right from the start to surprise her, then went slower and long to tantalize her. I put the tip of my index finger just resting on her asshole, but didn't push it in - I let her bounce back onto me and get just the very tip into her asshole. Meanwhile Tracy stationed herself behind me, rubbing her body against me, holding my balls from behind. she put her thumb into my asshole and started rubbing on my prostrate hard while Cara backed herself onto me. The feeling of something going in while being fucked by a woman, well nothing beats that. I pushed Cara off before coming, and Pulled forward off Tracy's thumb, and we all kind of collapsed into a heap, where there was a lot of kissing and fondling while we got our breath back - sometimes all 3 tongues touching.
By now we all started to wonder where I should cum, and the girls said why don't we take turns, they kneel next to each other, and I fuck them each a few thrusts at a time and then trade pussies. They knelt down and I was between them, they squeezed my cock between the two of them between their hips.
I decided I would give them each a bit more before I started on the final stretch, as I didn't think I could last much longer.
I put each thumb into each girl's asshole, and two fingers into each girl's pussy, and squeezed between them. Like all guys I have spent about half my conscious life fantasizing about double penetration, and the moans I got from those two girls made me more and more excited and I rubbed harder and harder, making Tracy squirt again, a bit more this time. Cara said she was enjoying that but now she wanted my cock. So I got the girls to turn and face the mirror, still on all fours, so they could watch each others faces as I fucked them. I started with about 3 thrusts into Cara. Then I gave Tracy only one half-in thrust before going back to Cara. She complained, I said, Let me surprise you. I gave Cara two very long slow thrusts, then the same to Tracy, and pulled right out so she thought her turn was finished. Then I went from outside all the way back in hard and thrusted long and hard about 8 or 9 times. She had been looking across at Cara when I pulled out, so she hadn't seen the look on my face when I went back in. She screamed loudly, and by now both girls' pussies were making squelching noises, but she was screaming so much I didn't even hear that. then I went over to Cara, gave her a slow push into her pussy. Halfway in I stopped and asked her if she wanted to take it in the ass. She said no, it would hurt too much as I was too big. Tracy said she would try, but next time. I thrusted a few more times, then switched back to Tracy. The breaks i took in between to squeeze tits helped me last quite long. Eventually I knew I was done - so I said, this is it, looks like you're going to be the winner Cara. I gave Cara just the tip, hovered there for a bit, and Tracy leaned over and grabbed my cock and thrust with her hand, bashing Cara's clit repeatedly. I shot my load all over her, and Tracy pulled my cock out and it felt like the tip would break off, but oh so good, I kept cumming, all over Cara's pussy and her asshole, Tracy still shaking my cock. we all collapsed onto the bed, and after a while Cara got up to shower. I lay with Tracy in my arms, and we kissed for a while, then she said, let's hop in the shower with her. We all soaped each other up all over and fondled a lot more, and I got my tongue into each girl's pussy again before it was over.
We all stayed over that night, sleeping naked in Cara's bed, and I fucked Tracy on the breakfast counter the next morning while Cara watched. I didn't last long then, but it was the first of many in the years since then. I have fucked Cara in the storeroom at her work, Tracy and I have made each other cum under the table in a restaurant. And I have had a threesome with Tracy and her husband, but that's one for another story.
Poster: Brian