SARD: Part 7 -When does a bisexual consider his virginity lost?

(Warning: This involves graphic material and not intended for anyone younger than 21.)


This is a topic that I have discussed, previously, on my last blog – Assentively Yours. But I thought I’d introduce it again on this blog, since I reintroduced my Sexual And Relationship Development. In my previous posts on the series, I mentioned some very introduction to sexual play with different people, but nothing had been full-out intercourse. I consider intercourse to be the defining moment of losing my virginity. Except, I had intercourse with a guy, before I had intercourse with a girl. So, I have always wondered what is the EXACT event that marks losing my virginity.

I was seventeen years old, when I first had intercourse and it was with a friend of mine named Dave – I mentioned him in this post here. It was probably a couple weeks after high school graduation when Dave and I got together and I agreed to let him have me. I won’t say it was a romantic situation (though there were times I had wondered what it would be like to be in love with a guy). Dave brought a porn movie over to my house and everyone in my family was gone, so we went to the basement where we kept our entertainment center. Dave popped the video into the VCR and we sat on the couch watching it. Eventually, we were both rubbing our own cocks and enjoying the scene. I don’t remember all of the details, but the scene in a movie portrayed a female anchor and a male anchor on the set of a news station. As the scene began it’s sexual action, Dave would ask me to do the things the female porn star was doing to the male porn star.

I was super excited to be with Dave, so when the female porn star began to perform fellatio on the guy, I did the same to Dave. I enjoyed his cock, a lot and loved putting it into my mouth. He was enjoying himself, as I stood in front of him and bobbed my head about and down. His pants were around his ankles and he had his hands on the back of my head and began to push my head down to meet the trusts he made into my mouth. After a few minutes, with Dave moaning and enjoying what I was doing for him, he pulled out and said, “Hey, can you do what she is doing?  Just pretend you are her.”

I turned around, and as I did, Dave pulled my pants down and I stepped out of them. The woman in the video was positioning herself into a riding position, where both her and the guy were facing the Camera. Dave removed my shirt and grabbed my hips. I stepped back and straddled myself across his legs. He positioned himself so that the head of his cock was pointing straight up and he began to guide me into lowering myself onto him. This was it, this was going to be the first time I let a guy fuck me. I was scared and nervous. I pushed downward, my hands on his knees, he pushed my ass cheeks apart and pushed himself into me.


My ass screamed in pain. It felt like I was burning and on fire and that I was being torn.  I tried to muster the courage to let Dave thrust into me a few more times. I felt so excited, but it was burning me, it was hurting so bad. But I wanted to make Dave happy, I wanted to be a good fuck for him and I wanted him to cum. I couldn’t take it any more. I whimpered and climbed off and told him it hurt too much. I ran to the bathroom, because I didn’t know what to do.  I could hear Dave chuckling a little. Fuckin’ prick, I could hear myself think. After I tended to myself and made sure I wasn’t injured at all, I went back out and Dave was stroking himself. He asked, if I was alright and then said we should have probably used some lubrication. Obviously, I agreed and asked Dave if he wanted me to stroke him. He smiled and said he did. So, I took his cock into my hand and stroked him furiously. He was so excited and tilted his head back as I roked his beautiful dick until he orgasmed and spewed all over my hand. I smiled at him and he stroked my head and thanked me.

Dave and I only hooked up a few more times after tha, mostly because I was leaving for college after the summer. I never got a chance to be fucked by him again, but I always had wondered what it would have been like to do it the right way. Granted, I have been with other guys, since then, but I felt something different with Dave…it probably had a lot to do with the fact that I had not let anyone inside me that way, yet. Granted, I had a few experiences that came close, but this was the first time for me.

The other situation, that I felt could habe been considered as losing my virginity, but with a girl was about a month after that with a girl I knew from school named Misti. I hate to admit this now, but I kind of used Misti because she had a reputation. It seemed like everyone I knew had already had sex (At this point in my life, I was so ashamed and confused about my same-sex attractions, that I assumed I was straight, since I liked women. “Bisexuality” was not a term used – you were either gay or straight and gay was wrong, so I “knew” I was straight). Although, knowing how much most guys brag, I’m willing to bet most of my friends had not had sex by this point in our lives. Well, I knew Misti was into me and I was flirting with her here and there.

Well, she invited me over to her place, one afternoon. We were sitting on her couch talking and I began kissing her. She seemed to enjoy it, because she began rubbing me all over and eventually began stroking my penis. We removed each other’s clothes and I was kissing her all over and rubbing her breasts. She then asked, “Do you want to do me?” Of course, I did, but I was extremely nervous. I wanted to be a good lover and I wanted this to be perfect. I already felt myself so excited, I thought I would ejaculate at any minute. I pulled out the condom I brought and put it on my penis. She leaned back on her couch and indicated that she was ready for me.

Okay, before I go on, please realize this is not some fantastical story and it is not a moment I am proud of in any stretch of the imagination…

What? it’s over?

Yup, that’s right, I began to orgasm almost immediately. I was so excited, I only thrusted into her a few times before having an orgasm. To make matters worse, both of our naivities (Maybe mine, because in hindsight, maybe she was trying to make me feel better), seemed to override any thoughts. She asked me, “Did you see my eyelids flutter?  Because, if they did, that means I came…”  Of course, trying to be the stud I assumed I was, I said, “Yes, they were fluttering so much, I thought a fan was blowing…”

Misti and I had also had a couple more hook-ups over the next few months. Nothing ever happened in the long run. I know Misti had gone on at one point to be an escort, because I had ran into her later on in life. She knew she had taken my virginity – well, at least that’s what I assumed at the time.

Anyways, there is my story of losing my virginity…and much like my own outlook on sexuality, I felt it had a dualistic nature to it.



12 thoughts on “SARD: Part 7 -When does a bisexual consider his virginity lost?”

  1. Oh wow. Losing my virginity reads like a romantic chick flick compared to yours haha. I lost mine to my boyfriend in college who was exceptionally patient and gentle through the whole experience. I’m glad I waited. The guys I dated before him would have likely pulled a slam, bam, thank you ma’am move.


      1. Does it? My husband jokes that my ex was a saint because at his age he would have likely done a slam, bam, thank you ma’am himself. I tell him all the time I’m glad I never knew him at that age. Lol

        But it certainly makes all the difference in sex when your first experience is in the context of love. At least, I think so.

        Liked by 1 person

          1. Perhaps, but he didn’t seem quite as enamored, which affected the experience.for the worse.

            Ah well. We can’t take those things back. I’m sure you’re grateful for the experience all the same. Sometimes experiences teach us what we want, but learning what we don’t want is just as important.

            Liked by 1 person

  2. Sex is sex, no matter who it’s with. my first time with a woman was with my ex wife and it was great because we were in love and both virgins. My first time with a guy was horrible and I wish I could erase it.

    Liked by 1 person

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