Visualization of myself: divorced, single 30 year old military male with brown curly hair and mischievous eyes. My eyes change between dark green to grey-blue depending on my mood, 5’6” with a athletic/ wrestlers build, a smile that is big and bright, average sized 6” cock, and an intellect that is highly analytical with a introverted personality that edges on extroverted and vivacious when with a date. I have a ‘harem’ of women (as one of my dates whom I see frequently calls them) that I cycle through bi-weekly, and am always looking to add to and date, get to know and fuck on a regular basis. Names always changed to provide anonymity.
I went to college a bit later in life and was a sexually frustrated 25 year old. I still hadn’t had sexual intercourse and was waiting out till marriage….though I had experienced oral sex. Several of the girlfriends / partners i played with did not want to take my virginity, but more than willing to sate our sexual desires through oral sex. Thus for the past three years I learned how to make women cum using my fingers, mouth and tongue to make them cum multiple times. Still to this day I am complimented on my fingering skills and said to have the ‘magic touch’.
As mentioned in my story ‘every hero has an origin story’ I used HotOrNot extensively during my college years. This was the time before Tinder, Bumble, OK Cupid, or Plenty of Fish, and it was there I cut my teeth on how to best prepare my profile to make myself sexually attractive online.
It was my junior year that I matched with *Donna, an attractive, thicc, Latina MILF who was in nursing school at the time. We bantered, complained about our busy schedules (me an engineering student / her aspiring RN), had intellectual conversations and talked military stuff (I was in the military program at my school and she was prior military). We exchanged numbers, texted all the time which lead to sexting. She mentioned her love for giving BJs as I relayed to her my love for eating pussy.
I did not tell her at any time I was a Virgin…I figured we would play it out and see how it went…
Eventually we agreed to meet and she met me near my campus. We went for a walk around and when we were secluded on a low rock wall we started kissing. It got hot and heavy instantly as we were both good kissers with just the right amount of tongue…leading to more kissing, licking and nibbling on her ears, neck and shoulders. I soon discovered her weak spot on her neck (seems to be universal lol) and used that to my full advantage. I had her enveloped in my arms, my hands roaming her back as they went lower and lower till I was gripping her ample ass. This ass did not know how to quit and I enjoyed walking behind her during our walk so I could admire it.
We continued deeply kissing and making out on the rock wall for a long while, till I ventured further down her shirt kissing along the way. I felt out her breasts through her clothes, and started moving her shirt and bra out of the way so I could kiss and suck on her tits. They were a small B sized cup, with large dark areolas and nipples hard and pointed out, as a good Latona MILFs should be.
We kissed and petted heavily for a long time until it was time for her to go, agreeing we should meet the next week.
We continued sexting and flirting with each other that week, telling each other what we wanted to do to each other. She described in great detail how she was going to suck my cock, and I detailed to her how I was going to fuck her until she cums all over my it.
For our second date I meet her again off campus by getting into her car, greeting her with a deep, sensual kiss and driving to a secluded parking lot. Once there we got into the back seat and started kissing heavily as I got on top of her, with her on her back. This time we had no qualms about taking each other’s clothes off, as we knew what we wanted to do to each other…
…while kissing her deeply and moving her to her neck and ears made her moan out loud, breathing deeply as she voiced her desire for me to fuck her. Ever being the gentleman…that’s what I intended to do.
To lose my virginity.
I took off her shirt quickly followed by her bra as I sucked, nibbled, and played with her breasts. I took my shirt off and she instantly started feeling all over my back sensually, and feeling along the waistband of my pants. I told her not yet, as I wanted to taste her first and make her cum on my face. I teased her by kissing and biting sharply on her stomach and waistline, before removing her pants. The pants being off, I started doing my signature move of kissing, licking, nibbling, and biting along both her legs for reaching her pussy. I first moved down along the left leg, reaching all the way to the feet before slowly tantalizing moving back up her leg, being sure to lick and tickle with my tongue under her knee.
I discovered along my journey of sexual exploration that the back of the knee is a highly erogenous zone that is underutilized…until I introduce my partners to it, I love to blow their minds with the intense feelings of pleasure ;-)
As I finished with her left knee I went up along her thigh biting and kissing along the way to her panty covered pussy. I could smell her strong scent of desire and her lacy panties becoming soaked with her juices. I kissed along it and then went down her right leg, the exact same thing I just did with her left leg. Kissing, nibbling, biting, and licking it making her increase in desire and teasing her greatly.
Finally I reached her pussy and took off her panties. Her darker latin skin contrasted nicely with her pink pussy, the outer lips of her labias being much darker…I admired it for a moment before taking my first lick, hearing her moan in approval and telling me she’s ready for me to fuck her. I keep licking and sucking on her clit, tasting her and savoring every lap of my tongue. She’s a very vocal partner so I always knew if I was pleasuring her well..I licked her till she came one time…two times…three times… four times…one right after another…
Finally let up as I was so hard and I wanted to fuck her. I had her as a squirming, blubbering post-orgasmic mess with just my tongue, she was very willing now for me to fuck her.
I rolled on the condom I had from my pants pocket (practiced several times on how to roll a condom on so there would be no issue when I got the chance), lined up my cock with her pussy. Donna has recovered a bit from her post-orgasmic bliss and was pawing at my hard cock and chest, whimpering how she wanted my cock. Desperate for it. I slowly inserted myself into her, feeling her warmth, wetness, and tightness surrounding me….it was blissful in the moment as I finally was no longer a Virgin…but also was cognoscente that I need to play my part as the experienced, dominant man in this sexual episode of my life…so I started to fuck her.
I started out slow as I had never fucked before, and did not want to blow my load before I wanted to and give the tell tale sign that I was inexperienced. Starting off with these slow thrusts allowed me to gain the rhythm to truly fuck her…to give her the pounding she deserved and so greatly desired. Pounding into her, thrusting into her sweet tight pussy, made her start to moan and sweat. I wanted to go deeper so I brought her legs up over my shoulders which I’ve seen in numerous Kama Sutra books and porn videos, and really got deep into her. I realized that fucking missionary is very intimate and also dirty, as then I can almost do anything I wanted yet be super close.
After about 5-7 minutes of fucking her in this way, I was ready to blow my load (i had masturbated before about an hour as i read that males last longer for sex after cumming). I could feel the tightening of my cum start to build in my balls, ready to be released. I let her know by grunting and breathing heavier as I started pounding even deeper and harder. She was begging for me to cum into her (the condom) and started talking dirty how much she loved my cock, she deserved my cum and wanted it badly. With that talk, it blew me over the edge and I started cumming. Hard.
It was exquisite! Ecstasy of insurmountable pleasure washed over me from my head to my toes and my cock and balls, shoved deeply into Donna. She held me close as i collapsed onto her, thrusting deep into her as i came.
I rested a few minutes on her, breathing deeply coming off my orgasm. Kissing her neck as she had kissed mine as i laid in her. Her gentle touch on my back and ass, caressing me as she cooed, loving the sensation of our bodies still combined after the intense fucking and pleasure rolling through us.
I got on my elbows and gently kissed her, and I could feel her smiling through our kiss as she was well sated and satisfied from our sexual encounter…I disengaged my cock from her to pull the used condom from me. I noticed at that time the windows were really fogged up from our heaving breathing. I threw the condom away and then we sat in the back seat chilling and holding another as we whispered sweet nothings to each other and bantered back and forth.
Finally we decided it was too late for another round and got dressed. Once somewhat respectable we both got out the back seat to the front seats, and she drove me to where she picked me up. I kissed her again, thanking her for the evening well spent. She then giggled and whispered the pleasure was all hers, and I got out to head to my dorm room.
We continued to have sex on and off again for two years after that encounter, most of them spent in the back of her car. We both moved away after graduating and haven’t been in contact since. She I do think of her often, and unfortunately did not get to see her DDs she bought as she had gotten a boob job after graduating RN school. I would have loved to broken them in with a proper pearl necklace, as she was definitely a cum slut.
Source: reddit.com/r/gonewildstories/comments/fj70p7/she_didnt_know_it_was_my_first_time_mf