Where it happened: Bedroom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
So I lost my virginity a couple years ago at age 42. How is that possible to be a virgin that long? I know, I know. And no, I am not a troll. But very low self-esteem and low confidence, plus my values that sex should be more meaningful than a one night stand or a night with a hooker, kept me from doing the deed prior.
I finally decided that I had nothing to lose by trying to date a woman and the Internet made it relatively easy to get a date. I told myself that I would flirt online, find a nice woman and then date her as long as I could, or at least until she dropped me, which I was convinced she would. (Wrong!)
I posted a picture and wrote a profile and within (seriously) one hour or so, there were five women who had written me. One stood out, an attractive 43 year old brunette and I began corresponding with her every day. She had a great sense of humor and was an excellent writer. We hit it off and about 10 days after I first met her online, we had our first date. She suggested a Chinese restaurant with great food and a quiet lounge attached. The date went fabulously well, the conversation flowed, and right there in the lounge after dinner, I stated that I wanted to kiss her. (She later told me that her gal pals thought this was so old fashioned–but it was my first kiss, and what did I know). Anyway, we had a nice PDA kiss right there in the lounge and I was amazingly NOT self-conscious, as there were about a dozen people in the vicinity chatting.
Afterwards, I walked her to her SUV and gave her a hug and next to her SUV, we again had a kiss, this time with mouths open a bit. I would say it was a restrained French kiss. She told me that I was a natural at kissing and I could feel myself getting hard right there in the empty parking ramp, pressed up against her warm body, lightly scented with perfume and body lotion. It was about Midnight.
We continued dating and kissing and making out a bit after dates or when I dropped her off. By about the third date she kept implying that we could have sex, and she wanted to, but we’d need to be tested for STDs first. She didn’t like condoms, but wanted to be safe. Fine with me, but getting the tests arranged and results exchanged, and doing so around our busy work schedules, took about two weeks. The results came back clean. Quite honestly, after fantasizing about sex for 30! years, she could have proposed that we wait six months and I would have been thrilled, not quite believing that a woman would find me attractive enough to let me do that to/with her!
It was a Sunday evening. She drove to my place and I made her the dinner she requested. She loved it, and we talked about an hour or two after about our families etc. Then she grabbed my hand and asked to see my bedroom. I was quite nervous by this time, in part because for probably two weeks prior, we had been sexting and I am pretty sure I had led her to believe that kissing was not the only thing I would be good at. Now, it was ‘put up or shut up time’ and I was kind of regretting all of that fast talk and double entendre in texting that I had done. My home is not that big, so the “tour” of my room basically involved a tour of the bed, which we sat down on. We began to undress each other. She had no idea that I was a virgin at this point. I had only told her that my previous dating experience was VERY limited. Conveniently for me, she had not wanted to share detailed sexual histories or “our number,” citing that beyond STDs, it was mostly irrelevant.
I remember my panic at the issue of the bra. Yes, the bra. I had Youtubed it, but had forgotten to buy one and practice, and honestly had never given two cents worth of thought as to how to hook/unhook one. I touched her bra in the front and casually ran my hands around back, pulling on the straps clumsily. She stopped kissing me, smirked a little and then made a funny comment about her bras being bullet proof. She took it off, and in short order I was staring at two beautiful breasts, maybe a B/C cup, but not big enough to sag. We kissed for several minutes while hands explored and worked at remaining clothes. She lay back, her head on the pillow, and I moved my naked body partly on top of hers. My penis was very hard. I ran my fingers over her breasts, tracing around the areola. I ran my tongue over her nipples and gently sucked, first the left breast, then the right. After a short while, her nipples began to harden into stiff nubs. Her breasts were perfect: pleasantly squishy, warm, full in my hands. I wanted to make pillows of them and rest my head on them forever. I kissed down her body, going lower and lower, below her belly button. She had a little pooch from her Godiva truffle addiction (not much), but I found it sexy as hell. She was close shaved into a landing strip, and soon there were her pubes on my face, like stiff bristles of a brush. I ran my warm, wet, raspy tongue down over her nether lips. Her hips twitched a bit. I didn’t mean to tease, but I guess I did. I kept going, planting wet kisses over her left thigh as I went. When I glanced up, her chest was puffed out, as though she were holding her breathe. As I got lower, I saw the red painted toenails that I love so much…hmmm…she had remembered. I lifted her legs up, knelt in front of her on the bed, my penis pointing straight out. To be sexy I put her big toe between my teeth and looked down at her. She giggled. She looked so damn hot, laying there, smiling up at me, all naked and shit. Her hazelnut eyes were warm, inviting, lover eyes.
I pulled her whole body to the edge of the bed and put a pillow under her head. Then I knelt by the side of the bed. I pushed her legs back and she hooked her hands behind her knees to hold them open for me. Next, I ran the flat of my tongue from taint to clit, a long, slow stroke. Again, and again, I did this. She moaned. “That feels so fucking good” were among her first words, if I recall correctly. She had kind of meaty lips, which I enjoyed sucking into my mouth. There as no odor at all. I moved my tongue up to her clitoris and gave it some attention. Her hips were now gyrating a bit. She told me it felt good, but she needed G-Spot stimulation. She asked for my fingers inside her. I put one and she told me to feel for the rough ridge at the top inside of her pussy. I was getting instructions. Very convenient for a virgin.
“Right there!” she said.
“Faster, go faster.” I did.
“Now push another one in there.” I did.
“Deeper, and go even faster.” I did.
“Now with the other hand or your mouth, do my clit. I need to feel both at the same time.” I did.
My first time was with a 43 year old woman, and by this stage in her life, she new EXACTLY what she wanted. This was going well, I thought. In no time at all, I was down there between her legs, pistoning my fingers into her pussy as fast and hard as I could manage, while at the same time strumming her clitty with my thumb like nobody’s business. It must have been hot in that room, because I remember working up a good sweat. Would she ever come, I wondered? A number of minutes went by and I continued to work her over. Deviations were met with curt instructions to “put the fingers back in” or “why did you stop?” I switched hands, without losing rhythm, and kept at it.
Finally, she told me she could feel it on the way.
“Oh shit, I’m going to cum” she said.
Her pussy got wetter, but I could not feel the orgasm much because I was still moving my fingers like a machine inside of her. I could see her body relaxing after 15-20 seconds or so.
I stopped.
“Can you keep going please? My orgasms sometimes come two or three at a time if I’m lucky…let’s see if tonight is the night.”
So I kept at it. Her face was flushed and her upper chest was pink. About one or two minutes later, orgasms #2 and then, very soon after, #3, came.
Finally, I could stop. I was a dripping sweaty mess, hot, and tired. I asked her what happened and she told me that she’s never been able to come from oral sex alone. She needs fingers. Who knew women didn’t all come from oral sex? I thought that was plan B. Guess not.
She told me that she wanted to feel me inside her now. My penis was completely deflated through this, and so I jerked it to get it going. She repositioned herself on the bed and I got between her legs kneeling. I ran my hard dick over her pussy lips to heighten the arousal for both of us.
“Put it in” she said, a bit breathlessly.
I slowly started to push my cock into her. It felt nice. Warm, wet, fairly tight. The usual descriptors for sex apply quite well, I suppose. I got my whole length inside her. I am on the high side of average and quite big around. She was smiling. The insertion had felt great for both of us. I began stroking faster. She urged me on even more.
“Go faster. That’s it. Give it to me hard,” she said.
I went down on elbows in missionary position, kissed her, and began to hammer away.
After about two minutes I was having trouble thrusting. My penis was getting soft inside her. I began to stroke more deeply, not pulling out too far. After about another 30 seconds, it became apparent that I would not be able to continue. I pulled out. She was wondering what was going on. I told her that I didn’t know. I managed to get it hard again by self stimulating, and then leaned into her and put myself inside her again. We went about another 90 seconds and it started getting soft again. I was not building at all to orgasm. I tried again and went another 1 or 2 minutes, before softening. Oh boy…I wasn’t expecting this. How embarrassing. Never in a million fantasies over 30 years had I ever expected an ED problem.
We tried different positions. Nothing seemed to help. I explained that I was probably just nervous the first time (with her). We tried for like four hours that night and into the early morning. Nothing seemed to work. I let her know that I found her attractive and that it wasn’t her fault. We eventually decided to call it for the night. Both of us were tired and I was plenty frustrated.
That would become our twice a week sex life, that repeated pattern, for about the next four months or so, until I eventually broke up with her (for reasons mostly unrelated to sex, although the sex did not help). Interestingly, she was always fairly satisfied with our sex life just because for her, the good stuff was oral and mostly digital stimulation, as well as kissing and foreplay. I have not had sex since then, nor dated, though I probably will at some point, since I really enjoyed the companionship. She was kind and nice, just not the right one.
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