S.A.R.D. #6 – To whom did I lose my virginity?

WARNING: I’m going to be discussing something of an adult nature. I am whipping this out as it comes to mind and will be thoughts that are raw and uncensored – I may or may not use vulgarity. Oh, and it may have tons of grammatical and spelling errors too (Oh, the horror!?!?!). This post is intended for mature audiences. Also, names have been changed to protect the not-so-innocent.


On my last Sexual and Relationship Development post, I indicated a time when I thought could be considered losing my virginity. but in this post, I’m going to mention two situations that occurred relatively close in time together – the first time I had intercourse with a guy and the first time I had intercourse with a girl. Granted, I recognize there might be too much information here, but I decided to share it anyways.  Obviously, for those of you that followed my last blog, this is not a new story; but the way I discuss it, might have some variances, because I’m whipping this post out from memory and some of the details might be inaccurate or remembered differently now as compared to when I last wrote about it.  Either way, it has always been a question of my own, since I took forever to accept my own sexuality – did I lose my virginity to a guy or did I lose it to a girl? And, does it really matter?


David and I were friends in high-school.  We were both part of a group of about 4 friends that went and did everything together. That’s code for “Mall Rats”, mind you…  Anyways, I’m not sure exactly how David and I started hooking up, but it began right after graduating high school.  We had a couple of interactions before we had intercourse. The first time we had done anything together, I had been over to David’s house and he had said something about wanting to see my dick and he wanted to show me his dick.  I was extremely reluctant about it and kind of played it off like we was joking.

At this time in my life, I had convinced myself that any attractions I had to guys were solely because of being molested as a young boy.  I assumed that there was no such thing as “bisexual” and tried to avoid any situation where that might be the case. I had not considered that I might have been attracted to David, but we were both part of a group of guys that hung out and laughed and hit on girls together, so it wasn’t like there was any glaring insinuation that there was anyone that was “gay” in the group (bisexual, wasn’t really a “thing” back then). So, having David start down these lines was a little shocking…

…and arousing…

I remember sitting in his living room with him as he pulled down his pants and pulled out his already erect penis.  He asked me if I wanted to touch it and I kind of shook my head. And he asked me to pull mine out. and I sat next to him and complied. David wasn’t someone I had thought about being attracted to, but he had a way about him that made me want to do this.  I pulled my pants down and my penis sprang to life. He then looked at me and said, “It’s okay. Michael and I have done this.” (Michael was one of our friends and I would have never guessed this about him). For some reason, hearing that, seemed to make everything alright as David grabbed my penis and began rubbing it up and down. I then grabbed his cock and began giving it a hand job.  He laid his head back and began moaning.

After a minute he said, “Put your mouth on it.” I leaned over, and put my mouth around the head of his cock as he pushed me head a little down on with his hands.  He thrusted to the back of my throat and I gagged on it and pulled off.  Then David returned the favor by going down on me.  We traded back and forth like this a few more times, before David said he was about to cum.  I pumped my had up and down on his cock as he shot jizz out and it went all over my hand.

I couldn’t believe we did this, but we managed getting together a couple more times before it ever led to sex. This time occurred over at my house and David came over to watch movies.  No one was home, my parents and siblings were all gone.  We had gone to the basement and David had brought a “movie”. It was actually a porn and he put it in my VCR and we sat on the couch next to each other. He made the first move and began rubbing my penis through my pants. Eventually both of our pants were off and we were jerking each other off. David asked me for a blow job and I complied – it’s almost like I enjoyed doing it.

I had been giving him head for a few minutes and sat up. David then pointed at the TV screen and said, I want to do what they’re doing.  The scene was a male and female news anchor and the male asked the woman to give the newscast while riding him. So, they were both facing the camera, with the woman riding up and down the male porn star’s cock.  David, grabbed my hips and turned me around to face the TV.  He pulled me back slightly, as I straddled his legs and began to lower myself to his cock.  It was still wet from my spit, but we didn’t think more of it as David opened my ass cheeks a little and I sat allowing the head of his penis to push at my anus.

The pain was fucking intense.  I tried to ride him up and down a couple of times, but I couldn’t handle it.  It hurt so much and I was so naïve and didn’t understand anything about this.  I jumped off his cock and ran to the bathroom, because I felt like I was on fire back there it hurt and burned so bad. I could hear David kind of chucking and asking what was wrong (Actually, years after the fact, I can see that he was kind of an insensitive prick.  I have another story about him and I together that I’ll share some other time). I told him how he hurt me that it didn’t feel right and I didn’t want to do it anymore this time. I had never had anal intercourse before, so I was unaware what was needed.  This wasn’t the only time David and I hooked up, but it was the first time I had ever tried anal sex and I felt like it was akin to losing my virginity to a guy.


It was just a couple of weeks later that I had sex with a girl.  Mysti was another friend of mine from high school.  In fact, I think Mysti had dated each of my friends at some point.  I hate to characterize anyone, but the best way to describe Mysti is that she was vulnerable and looking for someone to accept her. Well, I had dated a friend of Mysti’s earlier in my senior year of high school (Also a story, I’ll discuss at some time) and although that relationship failed miserably, Mysti and I had remained friends.  Well, up until we had sex, I had considered myself a complete virgin (At the time, I didn’t consider what I did with David as “sex”, because I was in such a state of denial about my sexuality, it was unreal).

I wish I could say something wonderful about the experience, but I was pretty lame – all things considered. I always liked Mysti, she was always so kind and nice and laughed at my silly little jokes too, so I felt an attraction to her. I felt at the time all of my friends had been sexual dynamos – at least they all told me how much sex they were having and I had never had any.  I remember feeling at the time, that I wanted to “save myself for marriage” (Yes, I realize the irony and complete lunacy of the facts of my life at the time…), but for some reason I felt I should be just like my friends. And I hate to say it, but I felt like Mysti was a victim to my desires to lose my v-card. And I took advantage of her hope in me to accept her willingness to be vulnerable with me.

So, one afternoon, I was over at her house and we were making out.  I’ve always been told I was a good kisser, so that was what I was trying to use to get Mysti in the mood.  We had been making out for a while, and I was rubbing her all over and she began rubbing my penis through my jeans.  She then got up from her couch and went to her room and came back with a condom. She told me, if I put it on, we could have sex.  Who was I to argue, huh?

So, we took our clothes off and I began kissing Mysti’s body all over and I was so excited, I felt like I would explode right there.  She opened the condom package and placed the rubber on my penis and rolled it down.  She then laid back on her couch and I pushed myself into her (okay, okay…I was new at this, okay…I had no idea how to do this or what I was doing). And I pushed myself in an out for all of 5 seconds, I’m sure. It was over, quick!  I lasted a whopping 5 seconds. I felt somewhat lame and stupid and asked her, “Was it good for you?”

Okay…before I tell you what she said, please understand that I had absolutely no experience with actual sex and looking back on this even, I’m sure Mysti had not been treated very well by guys in the first place. So, I’m not sure either one of us really knew what we were doing – in spite of her experience. So, it might seem like I’m mocking her by pointing out what she said, but it is more of a mockery of the situation with two naïve teen aged kids not knowing what the fuck either one of us were doing…

Her reply was, “Did you see my eye-lids flutter?  That means I came…”

I took it as fact and ran with it.  Seemed to me, I didn’t need to put much effort into sex (More on this at a much later date too).

So, there you have it. The two situations where I had sex the first time – one with a guy and one with a girl.  I always considered that the intercourse I had with Mysti was my first time and it’s what I marked as the time I lost my virginity. However, years later, when I came to terms with my sexuality, I think I lost my virginity with David.

But does it really matter?  I’m sure there are very few tales and stories about people’s first times being all glitter and romance, but then again, I also believe my thoughts and feelings are skewed from being introduced to sexual situations long before I was ready.

Please feel free to comment and discuss. I’m always open to people’s thoughts.

7 thoughts on “S.A.R.D. #6 – To whom did I lose my virginity?

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