So I made out with one of my blog followers.  Yeah, that happened.  It all began a few posts ago.  Perhaps some of you saw it.  She commented that it was too bad that we didn’t live in the same part of the country, because after reading my story she kinda wanted to take my virginity.


As it turned out, we actually did live in the same part of the U.S.  She was in the next county, as a matter of fact.  We quickly exchanged emails. Her name was Anastasia. The scoop was that she was 21 and she had a fantasy about taking a guy’s virginity.  And she was in an open marriage.  Yeah… erm… I wasn’t sure how I felt about that part.    But two out of three worked for me, and even if we decided not to do anything sexual I was curious to meet her either way.

We arranged the ubiquitous coffee date at a halfway point. I noted that she was gorgeous and very shapely.  Mmm.  We greeted each other, she got herself a drink, and then we moved further towards the back door. away from the noisy espresso machine and out of earshot of the employees.  The shop was small and we were the only customers, and I wanted a spot where we’d have free rein to discuss anything.

I shared some of my dating stories, we talked about our families, and of course we talked about sex. It was clear that she was into me and she asked if I was interested in getting it on with her. I said I was. She was strikingly beautiful. I knew I was going to kiss her. After two hours we each took a bathroom break and then called it a night.

We walked outside after setting up a tentative second “date” for the weekend.  She stopped and turned to face me and I took a deep breath.  Then she informed me that her husband was waiting in the parking lot on the other side of the building.  She didn’t have a car so he drove her.  Haha not awkward at all.   So if I was going to do it, it was now or never.

I hugged her, kissed her on the check, and then I pulled back a little.  We looked at each other for a split second and proceeded to make out for several minutes.   It’d been forever since I’d kissed anyone like that. It felt wonderful, way better than it ever did with Shorty.   I put my hands anywhere I dared – on her neck, up and down her back and her sides, and finally I reached behind and gave her lovely round ass an experimental squeeze.  Holy shit.  It felt so good to grab a handful of female flesh.

My memory is a little fuzzy, but I think it was at that moment that she started biting my lip.  We broke apart a couple of times to catch our breath, and at one point her hand drifted down to cop a feel.  She only touched my pocket and missed her target by a few inches.  Eventually things cooled down.  We said good night and parted ways.  But before we did she said, “Oh, one more thing!  I want you to feel my tits before you go.” She flipped her hair over her shoulder and thrust her chest at me.  I didn’t hesitate and cupped them in my hands.  She laughed and said, “I just wanted you to make sure they were big enough for you.” Oh yeah.  Definitely enough to work with there.

I’m still surprised at how okay I was with the whole situation.  I drove home in a pleasant daze.  The next couple of days I experienced a remarkable change.  Suddenly I was completely relaxed and comfortable around any girls I encountered.  There was no tension at all.  I felt like… like I was on a more even footing with them, I guess?  Amazing what a little kissing can do for you.  Unfortunately the effects wore off before long.

Anastasia and I exchanged a few scintillating messages during the rest of the week.  However our planned Saturday meet-up didn’t work out.  Things got crazy and the following week didn’t work for her either.  And then her planned move to Florida happened much sooner than expected.  I never got to see her a second time.  Damn.

It’s probably just as well, though.  I admitted to her that I was having second thoughts. She agreed that we could take things slow, but the open marriage was giving me pause.  While I was okay with making out and some fooling around, I wasn’t sure that this was how I wanted to lose my virginity.  Some of you are probably facepalming right now and about to tell me that beggars can’t be choosers, and I should have done everything possible to take advantage of the opportunity to just get it over with already.  But it is what it is, and I’m grateful for this bit of experience.

First dates:  30
Second dates:  3
Third dates:  2
Cancellations:  7
Stood up:  2
First kisses: 2
Sexual experiences:  0.6

23 thoughts on “Opportunity

  1. “I wasn’t sure that this was how I wanted to lose my virginity.”

    This is your head fucking with you due to your small warm fuzzy comfort zone. Just do it when you get the chance, it’s not that important.

    I lost my virginity to a 40yr old prostitute when i was 24. It took me 30min before i manned up enough to call, but in the end it was worth it as i got rid of the nagging voice in my head (the same as you felt much more comfortable around women after kissing).

      • Yup, and in hindsight i wish i had done it even sooner. The whole “first time should be special” thing is way overrated if you ask me. What matters more is the 2nd 3rd etc time.

        But to each his own, I’m not judging in any way.

            • Personally I don’t know how much of a confidence boost that would give me, knowing that I had to pay for it. I’d be flying much higher by succeeding naturally. But did it become a lot easier to get laid as a result?

            • I agree with you completely, if i had a chance to be with someone who wanted to be with me i would have taken it instantly. I had enough shit going against me, i just wanted to cross one thing off that list.

              I haven’t suggested you go and fuck a prostitute (i’d rather say that don’t do it, keep on going out and dating) i was just trying to say that if you get a chance like you had/have? with Anastasia, then go for it, there’s nothing magical about the first time. Sex is something that gets better with experience.

              It didn’t become easier, i was just able to be less stuck in my head = be more confident, care less about each interaction and word i say etc.

  2. Take it from another virgin if you chose, but i don’t think you did the wrong thing. If it’s not right it’s not worth it. However, when will the next opportunity arise?

  3. While I generally disagree with stuff like tangling with open marriages, I think this case is an exception. Beggars can’t be choosers. You really don’t have many other opportunities as far as losing your virginity. Ask her (Anastasia) if her husband would be ok with you having sex with her as means of her showing you the ropes and tell her what moves you would be comfortable with. I think this is an opportunity for you if the husband is ok with her having sex with you and teaching you the ways.

    Yes, she should respect your wishes to take it slow, however, this seems to be a golden opportunity, as she seems to have good chemistry with you, seems very nice, and is attracted to you. Tell her that you want to meet her in Florida sometime, and ask when you get there to meet her and her to show you the ropes. “I wasn’t sure that this was how I wanted to lose my virginity.” However, you don’t seem to have any other choice, based upon your previous experiences with women.

    Some people might think I am being immoral about suggesting this, but look at the reality. I commend you on your courage as far as finding dates, but you have had so few second and third dates. You have been stood up or had cancellations quite a bit. For your self esteem, and for you to gain the intimacy you desire with a woman, I would recommend trying to arrange to meet Anastasia in Florida. She is in an open marriage, which means she and her husband might be ok with you meeting up and teaching you intimate skills and giving you the intimacy you so very much desire and deserve. She could help you with intimacy issues, cuddle with you, make out with you, make you feel more comfortable in touching a woman intimately, and possibly have sex with you. Ask her if she and her husband can agree to have you be a sexual partner for her, as you have had some pretty trying and hard experiences in the past with women that hurt your self esteem. People might think I am the devil on your shoulder for suggesting this, but I see no other option in my opinion.

  4. Also, I’m in the camp of if it’s really an open marriage, of she’s not lying… then go for it. You get more and more of that ease with women with the more and more experience.

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