This is a continuation of the post Losing It about losing my virginity. It was originally going to be called “Losing It and Other Firsts”, but that post became so long that I had to stop. Now I’m going to tell you about the first time I had sex and throw in a couple of other firsts while I’m at it.
At the time I lost my virginity, I had a boyfriend named Bo. He was my sister’s boyfriend’s best friend and one of the sweetest guys I have ever dated. He was a couple of years older than me, very tall, tan, and thin, and extremely soft-spoken and polite. I will never forget the sound of his voice or that he had eyes that reminded me of the ocean: blue-green on sunny days, gray when overcast. He worked as a deep-sea fisherman, going out on the boat for 4-5 days at a time and coming back for 2-3. On his days off, he would ride his bicycle the 10 miles from his house to mine to see me, even before I agreed to go out with him.
We had only been “going out” for a week when my deflowering occurred. He was out on the boat when it happened, but expected back a day later. I was racked with guilt and therefore told him about it as soon as I got the chance when I saw him again. I made him break up with me, although he didn’t want to. I just couldn’t live with myself because even then I knew how he adored me. I truly felt the same, despite my actions.
He never gave up trying to convince me that we should be together, still visiting me as often as he could. A few months later, he finally convinced me to give it another try. It wasn’t long before I fell completely, madly, head-over-heels in love with him. By that time, he’d gotten his car fixed and didn’t have to ride his bike to see me. He was the first guy with whom my mom ever let me leave the house, because she knew what a good guy he was.
Bo never tried to push me or take advantage of me in any way. He always behaved himself like a complete gentleman. That is not to say that we didn’t fool around when we had the chance. I was quite the opposite of a perfect lady even then, as I am sure you might have figured out from my previous post. We would have long make-out and groping sessions whenever we were left alone.
Some amount of time before we had sex for the first time, he was the first guy to ever go down on me. I don’t remember much about it, whether it was good or bad. I do remember we were in my bedroom making out on my bed. (My parents had—shocker!!—left us at my house alone while they went to the grocery store.) I do remember him asking if he could kiss me “down there.” I won’t say I was aghast, but I was a bit taken aback. I don’t think I had ever thought about that before or even knew that people did that. He gently convinced me and finally I agreed. I was probably too nervous to really enjoy it, not least of all because I was afraid my parents (mainly my mom!) would be home soon.
When I eventually made him stop, he said to me, “Yours is the sweetest pussy I’ve ever tasted.” I thought it was a really big deal, but my friends tried to tell me it just meant he’d been with a lot of girls. I’ve never taken it that way. He just wasn’t that type of guy.
The first time I ever had sex was Saturday, April 11, 1992. I remember the date exactly because it was Bo’s birthday and 4 days after my 17th birthday. I can recall the exact outfit I wore, down to the lacy bra and panties. I picked everything out especially for him. The outfit I wore was all-blue tie-dye. It was a new outfit and I’d washed my white bra and panties with it so that the color would bleed onto them and they would match. Blue was his favorite color.
My mom had baked a cake for him, and after we ate some we left to “go out” for the rest of the afternoon and evening. What we did was go to his place. He lived with his mom still, so we couldn’t go right to his bedroom. We sat in the living room and watched television for long enough to be semi-polite. Finally we could wait no longer, and excused ourselves to his room.
Like many other tales I have shared, exact details are lost with time, but some bits have always stuck with me. We listened to Metallica, the black album, on repeat (it was 1992, after all). We talked for a short while, then kissed and made out for a bit longer. He undressed me sweetly and slowly. Once we’d closed his bedroom door, nothing was rushed. When we were fully naked, I’d shivered with a chill and nervousness, and his voice was so full of concern for me. He pulled a blanket over the top of our bodies to contain our warmth.
Although it wasn’t his first time, he was nervous as well. He fumbled a bit with the condom. I accidentally hurt his feelings when he entered me, because I asked him if he was in yet. He looked completely deflated and replied, “You can’t feel that?” I was immediately embarrassed and apologized profusely trying to explain that what I’d meant was, “Are you all the way in yet?” because I had been holding my breath. He had not gone all the way in because he felt me tense up. He took it very, very slow for me. I remember “The Unforgiven” was playing.
What followed was 20 minutes of sweet, tender lovemaking. That’s how I’ve always remembered it. I didn’t climax (I wouldn’t learn how to do that during sex for years), but when he did he wrapped his arms around me, looked into my eyes, and told me that he loved me. I may have cried a little bit and definitely told him that I loved him, too. We laid in his bed for a while, just holding each other.
Afterward, we put our clothes back on, went out in the living room again and watched Highlander 2 (yes, I know that movie doesn’t count). I recall next to nothing about that movie, other than being curled up against him on the couch. When it was over, we returned to his bedroom to go for a second round.
That next go-around wasn’t as slow and sweet, nor was it as short. We went at it for about an hour. The first time killed all of our nervousness, so we were free to explore each other more. His hands, fingers, and mouth felt so good all over my body. Bo was a very skinny boy and when we were done, my inner thighs felt all beat up from the blades of his hip bones. They were tender for all of the following week.
I had to be home by midnight, so our time together drew to a close. We got dressed and he took me home.
Unfortunately, Bo and I were only able to have sex one more time, a week later. It didn’t go as well that time, as I was on my period. I was grossed-out by the thought, but he convinced me it was okay. I got in two more firsts that day: first period sex and first doggy-style. However, I was unable to get past the blood, so we stopped and just cuddled instead.
Things got very hectic for him not long after that. His poor old 1979 Ford Granada died again. He got into a huge fight with his alcoholic mother. They had always fought a lot, but that fight was enough to finally drive him to go live with his dad far on the other side of town. He rode his bike to see me one last time. He said we had to break up for a while because he didn’t know when he would be able to see me. He didn’t think it would be fair to me to leave me hanging like that. I was heartbroken, but I understood. We cried together as we shared our true love vows. He promised he would be back for me one day and that if I decided to move on but found him again in the future, he would leave anyone in the world for me. It was one of the saddest kisses in my life when we parted.
I saw him exactly once after that, for less than 5 minutes. It was a few months later on the 4th of July. I’d gone to the beach with my mom and sisters for the Independence Day festival and fireworks. He’d ridden his bike 10 miles from his mom’s house to mine, only to discover I wasn’t at home. My dad had stayed behind and thus told him where we were. So then he rode the 7 miles from my house to the beach and searched the throngs of people for an hour to find me. He just wanted to tell me that he still loved me and missed me. Then he had to leave me again.
By a strange twist of fate, I finally had sex with Chuck for the first time later that night.