This true account first appeared as a Sexy Letter in Pip Caligulone’s Houseboat magazine. To read more about that singular publication, click here. (Speaking candidly, I wish I had read something like this in my larval years.)
Dear Houseboat, I never thought this would happen to me…
I didn’t realize until recently that going to a wedding without a date could be AWESOME.
I love weddings. I love wedding food. I love red-faced skanky bridesmaids. I love the sexy, chunky singer in wedding bands. There is so much sexual tension in the air, whether it’s from the unmarried aunts to the dirty, drunken toasts about the wedding night, to the fact that every couple there has a hotel room and left the kids with the grandparents. I think it’s the general combination of vacation and alcohol and an ancient mating ritual that gets everyone horny. Plus, even though more marriages end in divorce than in “‘til death do us part,” well, weddings are just about love and potential.
That is, unless you’re shy, like me, and dateless. Then it’s just frustrating. Or so I thought.
I’d broken up with my girlfriend at the beginning of the summer and didn’t work too hard at finding a date for my buddy Steve’s wedding. I went through the whole summer as the third wheel, as the single guy at barbecues. I never turned down invitations just because I was going stag, but I always had the sense that people felt bad for me. Angie, Steve’s bride-to-be and a fucking knockout who was as kind as she was hot, lamented that I couldn’t “close the deal.” And she was right. I don’t pursue women. They have to fall into my lap.
“I’ll have to find someone for you,” Angie said.
“Please don’t,” I said. I never do well on blind dates.
Angie seemed to take my refusal to heart (No means No, after all) and our group of friends approached the upcoming wedding weekend with excitement. Angie and (most of) her friends were guys’ girls, and they insisted on coming to strip clubs and getting lapdances with Steve and his groomsmen, which included me. I watched one particularly ambitious stripper try to give Steve a blowjob before Angie had to show her how it was done. I had high hopes for that marriage.
But I was still feeling sorry for myself and I headed out of the club for a smoke. Tanya, Angie’s cousin, was out there, too, smoking and texting. At first I thought she was one of the dancers until she called me over.
“Blow your load, Ray?” she said.
“Nope,” I said. “Strippers don’t do it for me. I think it’s the glitter and the melon body spray.”
“You mean a girl grinding her ass against you doesn’t get you hard?” she said. “I’m really curious. My ex-boyfriend LOVED strippers. Loved strippers too much…”
“Sure I get hard,” I said, liking that I was sharing a smoke with an attractive woman and getting to talk about my dick, which was stirring. “But that’s it. I get hard and then I remember I’m spending 50 bucks for it and the song is going to be over and I didn’t even like that song in junior high when it was popular. And then I think about the last time I came in my pants, which was a huge embarrassment …”
“…and probably also happened the last time that song was popular,” Tanya said, laughing.
“Naw, it was like three days ago at the gas station,” I said, and we both laughed. I’d read somewhere that making a girl laugh sends her blood rushing downward, but I wasn’t sure if my being self-deprecating fucked with my chances. Either way, I still wasn’t feeling confident, so we chatted for a while, even as she occasionally stroked my arm, and I found an excuse to go back into the club, like a chicken.
“Get me drunk at the wedding, OK?” Tanya said as I walked away.
“It’s an open bar, so that won’t be too hard,” I said, kicking myself.
Two days later was the wedding, and I was on the lookout for Tanya. She was on the bride’s side of the church, and she showed up wearing this short black dress. Totally inappropriate for a wedding, I thought, and some of the older ladies were giving her the side-eye while their husbands appeared profoundly uncomfortable. She looked great regardless of her scandalousness.
At the reception I was not surprised Tanya was seated at my table, even though I, as a groomsman, was paired with Angie’s humorless sister, Tina.
“I made some arrangements,” Tanya said, sliding in next to me, her bare leg brushing mine. “You’re the only person I know who’s not a relative. Time to make good on getting me drunk.”
“You’re the boss,” I said.
I returned with a couple of heavy duty cocktails and noticed more than a couple of guys giving me the thumbs up, as well as Angie from the head table.
“You blushing or having a heart attack?” Tanya said.
“I’m blushing,” I said.
“Yeah, they think I’m the whore cousin because I’m divorced,” Tanya said. “This family stays married no matter how much they hate each other.”
“You don’t think Steve and Angie—?” I said.
“Oh no,” Tanya said. “They’re going to be great. “Angie knows how to keep him happy and he treats her like the treasure she fucking well is.”
“She is!” I agreed. “If she weren’t with Steve, I’d…” I trailed off.
“You wouldn’t do a goddamn thing,” Tanya said. “Angie told me that you need girls to fall in your lap.”
“So I’m going to fall in your lap tonight, OK? And then I’m flying back to Minnesota, and maybe that’ll kick-start you out of this mopey behavior. All I want you to do is one thing.”
I couldn’t believe that I was hearing this. She just kept looking at me, a little smile on her face, an arm thrown casually around the back of my chair, her other hand in my lap under the table.
“What?” I said, growing in her hand.
“Ask me out.”
“What?” She was still squeezing my cock through my pants under the table, still looking at me with that smile, still with her arm around my chair like we were best friends.
“Ask me out. Don’t be scared. I’m gonna fuck you tonight. I find you really sexy and I have high hopes for that piece of meat in my hands. Now just ask me out.”
“Tanya, wanna go out sometime?” I said.
“Oh, Ray!” she said. “I think you’re really cute but I’ve got a boyfriend! But you made my day!”
“What?!” I said, my cock going to half-staff immediately. “That’s a shitty thing to do!”
“Ray,” Tonya said, never breaking eye contact. “I’m fucking you tonight. And you know what? Asking someone out and getting refused isn’t the end of the world. Just don’t be a dick about it. If you fail, try again. That’s all there is to it.”
Tanya made a point to grind her ass against my crotch during the fast dances, and press her breasts against me during the slow ones. We both drank just enough to keep it light but we were both aware not to drink too much. At the end of the night I couldn’t keep my hands off her.
We fell into her hotel room and I didn’t even wait to get past the bathroom. I turned on every light, bent her over the sink, and lifted up her dress, pulling her panties down. Her shaved pussy glistened as she parted her thighs. The panties had slid down to her knees and she still had her shoes on, so I grabbed her hips and eased myself into that especially tight opening. I just needed to be inside her. I watched her mouth open, soundlessly, as she gripped my cock with her toned snatch.
“Tanya, will you go out with me?” I said, pumping, spreading her legs until her panties ripped and fell in a wet heap to the bathroom floor.
“Let’s keep it a secret from my boyfriend,” she said, playing my game. “He’s going to wonder why my pussy’s wider and why his favorite pair of panties is missing.”
“You like cheating on your boyfriend with me?” I said, slapping her tight ass.
“He’s not going to know unless you pull out and come on my dress,” she said.
And that’s exactly what I did. I pulled out from her tight, soaking hole and sent the warm jets across her lower back and the bunched material of her black dress. I pulled it off her and wiped my come off her back and pussy with it.
After a brief nap on the bed, we woke and fucked two more times before breakfast, then I drove her to the airport in place of a cab. We kissed warmly at the drop-off area, and we have stayed in touch.
The next weekend, at a party, I struck up a conversation with a single woman with a dazzling smile and a cute dress. At the end of the afternoon I asked her out and she said Yes.
—Ray L. Seattle, WA