I wasn’t blessed with a pretty face. Even with makeup and such it seems to be barely passable and I wasn’t asked for dates in high school. But I wasn’t a virgin then and I’m not celibate now, years after graduation.
Nature gave me a decent body and lots of brains though, and I used them. No boyfriends meant I doubled-down on academics and had my bachelor’s degree in a high-paying technical area by the time I was eighteen. My first income went to a plastic surgeon who fixed my nose and made my breasts more appealing but only slightly bigger. I had exercised diligently so was trim and strong.
If my peer males didn’t want me then I didn’t want them either. I’d studied sex along with math and was quite ready for my first sexual encounter as a junior in college at age seventeen. It was the old babysitting for the single dad situation as I earned income to avoid student debt.
Ralph was a nerd like me whose wife had run off with a biker, seeking adventure and leaving him with two school-age children. He worked nights so I could take classes when I needed to and study after the kids went to bed.
There was some magnetism from the start so I made my availability clear about a month after beginning work. Looking back, he wasn’t the best of lovers, but certainly good enough for my first times. He gently, then vigorously, worked through my nervousness as it turned to passion and pleasure. I remember how I marveled that the real thing was so much better than a dildo. And the hot cock spurting flooded me with pleasure as it filled me with semen. He had a vasectomy, another reason for my decision to use him.
We actually used each other, as often as possible when he arrived home from work and sometimes when we could arrange it on weekends. There was even one memorable trip when I went along as “nanny”. Spending the whole night together was special. He sometimes dozed off after our finale and I loved to fondle his shrunken cock and his balls, holding it and moving it around, marveling at it and what it did to me. That might cause it to awaken again and I’d pleasure it with my mouth, urging tumescence for another sensuous visit to my hungry twat.
When I moved away for my first job and got my bodily makeover, it was time to expand my horizons so I invested in an IUD. Now was the challenge of finding compatible sex partners. Notice that I used the plural. Monogamy wasn’t a necessary part of my moral structure until I made a life-partner commitment, and it might not be then either.
I had decided that older men were my best “market” so Saul, who lived in my apartment building, had potential. He was fifty, reasonably fit, and worked at home. We spoke on the elevator and at the Thursday night wine and cheese socials. He got the hint and asked me to dinner and a show. Then dinner out and finally dinner at his place. I wanted, and got, trouser trout for the second course then breakfast in bed. I was motivated to investigate the anatomical differences between him and Ralph a few times during the night and he was very obviously helpful.
His sense of humor was delightful. I’d never laughed through an orgasm before. Nor showered with a man. He’d been around and I loved his sharing what he’d learned as well as his imagination.
We talked too. I always wanted to absorb wisdom from people further along life’s path than I was. This was where I got my first lessons in multiple sexual relationships. He told me about Marie, a woman about his age that jumped his bones (or boner :-) )about once a week. She lived with a younger guy, Jimmy, but had been banging Saul before she met him and saw no reason to stop. She knew about me and wanted to meet.
Marie and Jimmy and I had finished dinner together at Saul’s place when the host announced, “Marie and I haven’t been together for more than a week. Please excuse us for a while. Help yourself to dessert.” As they went off to his bedroom and closed the door, I looked at Jimmy and said, “If that is their definition of ‘dessert’, I’m game if you are.” We’d hit it off during dinner.
He grinned, “I was hoping you’d say that. Let’s go to my place. Leave them a note.” It was a nice walk and he took my hand. He was a 30ish Latino guy, shorter than me and more rounded. Polite and friendly. I took my time getting acquainted with his body, only the third man I’d been naked with. This ready rod was shorter and thicker than my previous two so I played with it so long that he asked me if there was anything else I wanted to do with it. It was uncircumcised and I was fascinated with the foreskin.
When he got between my thighs and his mustache tickled them as his tongue tickled my clit, I was his. I came the first time as I was stretched inside noticeably more than usual. And the second time as he skillfully worked on my tits and sensitive vaginal areas, and a third as I was strongly flooded with more hot semen than usual.
Jimmy was very proud of himself and admitted that I was only the second woman he’d pleasured. I told him he was my third and Marie had apparently trained him well. In the spirit of disclosure, I proclaimed that this was the first time I’d had two men the same day, having screwed Saul before they arrived for dinner. That got him going again and I got on top to show him my skills.
Marie texted that she was going to spend the night there and I said I wouldn’t miss this opportunity either. He dropped me off at my building on his way to work, promising to stop by before he went home. I texted my boss that I didn’t feel well and would work from home today. I diddled myself repeatedly as Jimmy’s cum kept oozing out and asked him to be gentle as he joined me in my bed on his way home from work. After we screwed I suggested he save any energy had left for his housemate. He was welcome in my bed anytime, just text or call first.
Saul teased me when we got together two days later and quizzed me about how busy my bed had been since he saw me last. I gave as good as I got, pointing out it wasn’t just my bed but my couch, carpet, and shower that were locations for unbridled lust. He didn’t need to be gentle even though Jimmy had thoroughly exercised my pussy after work because it was getting nicely in shape for repeated coitus, thank you.
We had a playful fuck as he explained the dinner scenario had been Marie’s idea, wanting Jimmy to spread his wings and she thought I’d be a good candidate. I said to give her my thanks. I especially noticed the sensations his cock-shape gave me after recently having Jimmy’s. Sex was FUN!
I was really getting into having more than one lover a day. When I asked Saul how he liked getting so many “seconds” he laughed and said that’s what he’d usually been getting from Marie. His ex-wife wouldn’t do it.
My self-image and confidence were rapidly improving so when Jimmy’s younger brother Willy 4came to visit I boldly said, “Your place is too small for guests. Why doesn’t he stay with me?” I only have one bed so the implications were clear. Jimmy swatted my butt and chortled, “Will I ever have any time with you with him around? He’s hung better than I am!” I reassured him with a wiggle of my ass.
“Very true,” I thought as I slurped his also uncircumcised shaft with the big mushroom head. Willy’s meat was as fat as Jimmy’s and maybe an inch longer. I quizzed and he’d had some fun with girls but it was sporadic and apparently of poor quality. “I’m going to change his perspective on sex,” I thought.
He was so eager that we went right to the main act. Just as I expected, splashes painted my depths in just a few minutes. Wrapping my legs around him, I wouldn’t let him exit and told him to keep moving slowly. “You’re just the right height to give my girls a lot of pleasure. If you want to stay where you are now then get busy making me feel good.” My nipples are well connected to my pussy so his eager stimulation, together with that big log up inside me, brought me to a quivering orgasm. When he asked what happened he was very pleased with himself. He was fully hard again so I rolled him over and showed him a whole new way to fuck. He held out a lot longer this time and I gently squeeze his balls as he pumped his second load inside me.
For the next 48 hours I got laid a hell of a lot. Not all I could handle, I found out, but all three men could deliver. I began to realize my capacity for sex and the guys were impressed. I guess you could say that they played the game “hard”. <grin> Jimmy found out that the best way to spend time with his brother was in my bed. They took turns as often as they were able and were a big help like going out for or fixing meals, or washing the cum-stained towels which kept my bed clean. Saul stopped over morning and afternoon each day to contribute his six inches to the event. We weren’t sure how to keep count, certainly my multiple orgasms were the best way. The guys did mark down their ejaculations on a pad but sometimes they would pound away at me for a while without coming, especially the second day, and then let another guy “ride the horse for a while” well they rested up for another go.
All of that wonderful male fluid kept my pussy well lubricated. I’d watched some gang bang videos and wondered how they could do it. Well, now I knew. I was a gang bang slut myself, and proud of it too.
After his brother left, Jimmy opened a bottle of champagne and toasted me, the most wonderful girl he had ever met. He professed his love to me and said he wanted to be my husband. Wow, I hadn’t expected that as an outcome.
As I sat there, with possibly a couple billion sperm from three men swimming around inside me, faced with an interpersonal situation unlike any I’d ever dealt with before, and all I could do was clam up. Sure, I liked him a lot, and he’d put probably half of the sperm in me and watched most of the rest, but I didn’t love him enough to tie the knot.
Finally, I was able to get my wits together, “I’m not sure what to say, Jimmy, and I sure am honored by what you just said. I care a lot for you but just don’t feel ready to take that big step. It’s not you, it’s me. Can we just keep things going and see how it works out? I won’t say never, but I can’t say yes right now.”
Of course he was disappointed, but he took it like a man and I gave him full credit for that. I think I knew deep down inside he was not “the one”, but then I wasn’t really sure who that might be. I hoped I would know more clearly the time came.