Pizza Delivery Boy Part 2: Dean’s First Threesome

I think this sets the record for longest gap in time between Parts 1 and 2 of one of my blog posts. As long-time readers of the blog will recall, or readers who want to bone up on Part 1 of this story will know, I was a Domino’s pizza delivery boy my senior year in high school, and one particular Saturday night I got the call to deliver a $5.50 small cheese pizza to a nearby apartment complex, while my compatriot Aaron, to whom every cool incident happened, got the choice $18.00 large everything but anchovies pizza to deliver to a different location.

Lucky Aaron. All the good stuff happened to him.

But unbeknownst to all of us, waiting at the end of that small cheese pizza order was a lovely woman named Beth, who was in her early 20s and claimed to be down from San Francisco for the weekend visiting a friend. (Who was oddly non-existent that evening, but who’s to judge?) Who said she was bored, and so ordered a pizza. And was hoping the delivery guy was cute.

I guess I passed the test because I ended up hanging out and fooling around with her. After making land speed records back to my Domino’s location to get clocked out - because despite my thirst for sex, I’m responsible that way. She was still waiting for me so I got her naked, kissed her and played with her tits. And ate out her pussy. She seemed to like what she received because she got my phone number and asked if she could give me a call some time. I was happy to oblige.

Now keep in mind that this was 1984, so phone numbers were actual phone numbers. To a phone in a fixed location, that rang and you answered it. Younger blog readers may have read about such things in their history books. The only phone number I had, which I gave her, was my family’s home phone. Which sat in the kitchen. And another phone sat in my parent’s room.

The next day, a Sunday, I was at home shooting baskets in our driveway when my mom shouted to me that I had a call. It was from a girl named Beth, and did I want to come in to take it.

Keep also in mind that I was a senior in high school, which would have made me 18 at the time. I was the oldest child, living at home with my parents, and any sort of discussion of sex or even girls with my family was awkward and I avoided it like the plague.

So the mention of the name of this woman with whom I had this amazing encounter just the night before struck me like a lightning bolt. Tingling all over, fighting to keep my composure, I came into the house and told my mom I’d prefer to take it in the back (in my parents’ room).

I picked up the receiver, waited to hear the reassuring “click” of my mother hanging up the line in the kitchen, and in hushed, furtive tones bid my paramour from the previous evening hello. I was a bundle of nerves, partly just from her call, and partly because she called me here, at my parents’ house. I could barely breathe. But she was graceful through it all and acted as if nothing was amiss.

She asked me what I was doing and I told her not much, just hanging out at home, practicing basketball. She asked if I wanted to come back to the apartment and see her again - along with a friend of hers.

If my heart was racing before, it went through the roof when she said that. I remember barely being able to gather enough air to form words, but I was incredibly excited at the prospect and told her that yes, I would like to meet her and her friend.

She then warned me, “just so you know, my friend is a guy.”

Hmmm. I’ll freely admit that I was a little bummed to hear that I wouldn’t be sharing a bed with two lovely ladies that afternoon. But it was still an amazing offer. For 18-year-old me in 1984. It was something I’d never done before. And even at that age, I was the same person I am today. Totally up for anything, and eager to experience all that life has to offer. So I told her absolutely I would do it and we made a plan to get together in 30 minutes at the apartment where I met her the night before.

I told my parents I was going to see a movie with this girl, made up some reason for how I knew her (I probably said I knew her from school or met her through a club), and headed to her place.

When I arrived she greeted me and introduced me to her friend Barry. He seemed older, maybe in his 30s, about my height, with a little extra flab around his middle. Although for the record I have to smile a bit as I now characterize someone in his 30s as “older.” He was perfectly nice and shook my hand, and after the three of us stood there awkwardly for a moment they ushered me in and we sat around the living room.

They told me that they were casual friends, and that this was the first time the two of them had done anything like this. I suspected they were actually dating and that Barry had been there the night before, getting voyeuristic thrills as he spied on me bring Beth to orgasm. I already knew the pizza order was in the hope of getting a cute delivery guy, but now I suspected the two of them had orchestrated it together. But I had no evidence to back up my theory and kept my suspicions to myself.

They asked if I had ever done anything like this, and I told them I had not. They laughed and said that it was good that I was getting a head start on my sexual activities for college.

Eventually the small talk ran its course and the three of us sat together on the couch, with Beth in the middle. I leaned over and kissed her. She returned the kiss enthusiastically, reaching down to grab Barry’s cock.

At this point I was hard as a rock. Readers who know me in real life can testify to the fact that I’ll get hard at a moment’s notice (in the right situation of course), today, in my early 50s. You should have seen me at 18. I was a regular bundle of hormones. Practically a walking erection.

Strangely to my eyes, though, Barry remained flaccid, despite Beth’s best efforts. Eventually we started removing articles of clothing and migrated to the rug on the living room floor. I shifted my attention to kissing Beth’s neck, arms, breasts, and stomach, eventually making my way to her parted legs and wet, waiting pussy.

While I was enjoying her sweet vagina for the second time in as many days, Beth gave Barry a blow job. I was more focused on what I was doing than on the two of them, but I never did see him get hard. Eventually she came again with my tongue on her clit, and immediately afterward she called out, “fuck me, Barry, fuck me now.”

He scrambled over and tried inserting his penis, but it wasn’t firm enough to go in. Instead he played with her pussy and even went down on her a bit, as she continued to writhe and moan in ecstasy.

At this point I was relegated to the role of spectator. Perhaps later in life I would have moved in and asserted a role in the melee, but at this younger age I was more inclined to take their lead. And once she had come, Beth was completely focused on Barry. This is part of what led me to believe they were dating, or at least more than just the casual friends they made out to be earlier.

I was a little bummed, and a little jealous, because I had this perfectly hard cock ready and raring to go. And some condoms, by the way, which I was in possession of because I had already been having sex with my high school girlfriend, with whom I had broken up a few months before. But no one had eyes or interest for me, so I just got to watch this woman who so desperately wanted her man to do her, and this man who was so desperately unable to do so.

Another thing I thought about (long) afterward was whether they had a cuckolding relationship and perhaps watching her play with other guys was what turned him on. Although if that was the case, it didn’t seem to work that day.

Eventually they gave up and collapsed in a puddle, cuddling each other and murmuring soft nothings. It continued to be clear that I wasn’t really part of the party any more, so I just sort of hung around awkwardly for a while before finally bidding them adieu, dressing, and leaving. They were perfectly nice as they wished me goodbye but I could tell they were done with me and that it would be a permanent parting.

It’s interesting when I look back on the actual encounter now and compare it to those I have today. It was a bit awkward and fumbling, compared to the smoother, more graceful dances I orchestrate now. The connection was more two-way between Beth and Barry, which is something I work painfully to avoid now, engaging with everyone and working to make sure all parties feel fully involved. And while I gave pleasure (twice), it wasn’t really reciprocated (either time). Not that that’s really here or there. It just meant I had to go home and masturbate - which I did multiple times that evening. I am lucky though that I get to both give and receive in the group sex I have today.

So it’s funny. In a way, it was a sad, awkward little threesome. She never got fucked at all. I never really connected with the two of them. Both guys probably left feeling our goals were unaccomplished.

But I didn’t really let any of that get in the way of my triumph. I was 18 fucking years old. A senior in high school. And I had just had a threesome.

With an older woman and her male friend. A woman whom I met by delivering a pizza to just the night before.

Damn. Was that hot or what?