Back in 2002 I was 25 and single. My mom and sister shopped at a fairly high-end department store and met a young lady working at the make-up counter. Knowing I was single and being impressed with this girl, my mom asked if she was single and would like to meet her son. The girl had a boyfriend, but mindful of keeping a good customer happy, she had a single friend named Jenny who might be interested. She said maybe she and her boyfriend and Jenny and I could go on a double date.
So basically I would be meeting not just one but three strangers, but the idea intrigued me. I arranged to meet all three at a restaurant. Dinner was a success. The girl my mom met was affable. So was her boyfriend, who was a 1st year law student. I was in my second semester of my second year of law school so we had that in common. The ironic thing was that while the girl from the make-up counter my mom wanted to set me up with was cute, Jenny was actually much prettier. She was Jewish and looked like a young (early-1970’s) Barbara Streisand. She had sandy, blond hair, was tall and athletically built with what appeared to be a nice round ass.
When dinner ended I asked if Jenny wanted to go to a bar with me. She did. We were able to get to know one another better and when I dropped her off at her apartment, we had nice French kiss.
We agreed to go out again – just the two of us, and the following weekend, we did so. Turns out Jenny had just moved into her apartment and this time she invited me up after dinner. I had hoped she would, and I had a three-pack of condoms should she be willing to have sex on our first, real date. We retired to her brand new couch. It was black cloth with the back cushions in a printed zebra pattern. We started hooking up. I fingered her and learned by my touch that she had closely shorn but ample pubic hair. As I fingered her, she unzipped my pants, loosened my belt, and took my erect penis out to start stroking it.
Now here’s where I have to tell a ‘story within a story.’ I apologize for not providing much of a segue, but, when I was in college, my freshman year I pledged a fraternity. Most of the guys – especially the older ‘brothers’ – were mean-spirited jerks who drank too much and did too many drugs. But one guy, Dave, who was a year older than me, was actually a really nice guy. Everybody liked Dave. He was no more than a recreational drinker/weed smoker, and he did well with the ladies. One of his stories was legendary. One night he was hooking up with a girl in her sorority house. A total no-no no matter what college you attend. Worse still, this was in the common area/lobby on a fairly fancy sofa owned by the sorority, itself. The girl gave Dave a hand job and as often happens when a girl strokes a guy’s cock, he ejaculated. Apparently, this ejaculation went all over the lobby couch and left a noticeable stain. The girl was basically put on trial and the president of the sorority demanded that Dave pay for a new couch. I felt pretty bad for him because he was so harassed by the top brass of this sorority that he, in fact, paid for a replacement sofa. But he was a good guy and the gal who gave him the hand job was pretty much being persecuted by her sorority sisters so out of goodness to her, he paid up. I probably took the wrong lesson from this legendary story, but ever since I heard it, I wanted to cum on a girl’s couch. Not necessarily a sorority couch and face the turmoil that Dave did, but I just got a kick out of the idea of ejaculating on a female’s couch.
So fast forward seven or so years, I’m 25 getting a hand job on a girl’s new couch. Jenny’s hand job is as good as any I’ve ever had. I turned my body slightly so my cock is pointing at those zebra-patterned back cushions. Jenny didn’t seem to mind and kept on jerking me off. Soon thereafter, I experienced my first orgasm of the night (I know, I know, ham-fisted foreshadowing). I think the combination of Jenny’s masterful ‘handiwork’ and the idea of fulfilling my fantasy from seven years earlier caused me to have a pretty intense orgasm followed by an equally intense ejaculation. Suffice it to say. by the time I was through, the zebra cushion had a lot more white stripes than black.
Jenny suggested we go into her bedroom, which I was glad to do. Even though I came a lot, I still wanted to hook up some more. I especially wanted to see Jenny’s vagina and eat it out too. Jenny had other ideas. She got naked as did I. She had nice, sized pointy breasts, a nice, curvy ass, but free of any cellulite, and I was able to now see her shorn triangle of sandy blond pubic hair. We kissed and I got hard again. Jenny asked if I had any condoms. I said I did. Now if you’ve read any of my other posts, you’d know that I never had any luck with condoms. I tried the normal Trojan-ENZ, Magnums, and Magnums-XL’s. Nothing worked. I’d either lose my erection in the process of putting it on or during penetration. I just couldn’t feel anything.
I gave it the old ‘college try’ with Jenny. The first two I was unable to maintain my erection when putting them on. The third, I managed to keep my erection, and I did get somewhat into her pussy, but I lost it trying to insert all the way. I did what I normally did in this situation and suggested we 69, which Jenny was game for. I actually thought it was very sporting of Jenny because having ejaculated once already, my cock was still pretty slick with semen. There was also quite a bit of cum in my pubic hair. I could smell it and I thought, “Man, if I can smell my cum from here, her nose is right there.” Therefore, I was actually relieved when her vagina was hovering over my face that I detected some odor in her folds. Nothing horrid, but just enough stink to kind of events playing field in light of my cum-smell.
I started licking her pubic hair along her labia majora. Jenny then did something kind of funny. She sat on my face to such an extent that her entire vulva descended into my mouth. It felt like I was being gagged with a fuzzy tennis ball. I breathed through my nose as best I could and attempted to lick her labia minora and clitorus in this manner, but eventually I had to get her on her knees so there was a little bit of a buffer between my tongue and her vagina. Once I did this, I was able to spread her lips apart, kiss her clit, and stick my tongue in her opening. Eventually, she came (or so she said).
Meanwhile, her fellatio was very good, and I was feeling like I could cum again. She made me orgasm and this time I gave her plenty of warning and announced, “I’m gonna cum.” Perhaps having already tasted my cum for the past 15 minutes, and not wishing to soil yet another piece of her furniture (her bed), Jenny took my penis out of her mouth and jerked me off on my abdomen and chest.
Though we didn’t have sex – at least not past the tip for a second or two – I left fully satiated and I hope that Jenny did too.
Source: reddit.com/r/gonewildstories/comments/nknrxj/when_my_mom_indirectly_fixed_me_up_on_a_blind_date