Strapless - Cover

Strapless

by Xander

Copyright© 2025 by Xander

Erotica Sex Story: When your lesbian friend makes an immodest proposition involving strap-ons, the reluctant young man takes her up on the offer.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Reluctant   Lesbian   BiSexual   True Story   DomSub   Anal Sex   Masturbation   Oral Sex   Petting   Sex Toys   Hairy   Size   .

A long time ago, the angry young Xander you already know and love was working as a waiter/bartender at the Fruit Bat & Crocodile Café in Atlanta. It was a nice joint. It catered to the after-movie, after-theatre crowd - we got busy at ten or so, and stayed that way until closing at 3 a.m. Needless to say, it fit my night-owl lifestyle perfectly.

I’d been there for a bit more than a year when Lauren started. Now, if you’ve tended bar or waited, you know how incestuous a restaurant “family” is. Everybody is fucking everybody all the time (usually drunk as the sun comes up). When someone new enters the mix, there’s practically a stampede. Well, as it happens, I slipped in first to meet our new executive chef.

Mondays were usually dead - no theatre, no symphony - so it was a shock when the night positively exploded. We were slammed from around eight until after midnight, so everyone on the small staff was totally beat when the time came for me to line up the shooters for our shift drink after the rush. Everyone in the front of the house knocked theirs back, and I poured an extra one to carry into the kitchen (and another for myself, natch).

I made my way to the back and found Lauren cleaning the pasta machine. We talked for a bit, and I handed her the drink - a kamikaze, probably. We clicked glasses, and I took a good look at her as she drank it down without even a wince.

Lauren wasn’t traditionally attractive. She had this total tomboy vibe that I was into, though. Great eyes that were gray and catlike and hadn’t seen any makeup for a long, long time. Her breasts were very small, and her figure wasn’t very womanly, but God, she had great arms. Sinewy and covered in a multitude of tattoos. She had a number of piercings as well, but it would be a long time before I knew that. Her shoulder-length brown hair stuck to her head - it was hot as hell in the kitchen.

“I’m gonna go down to Dark Horse when we’re done here,” I said. It was an after-hours tavern that catered to restaurant and club people after they were off. “Want to come?” Lauren hitched up an eyebrow at me.

“I’m pretty beat,” she said.

“How about some other night? We’re both off on Wednesday.” Now Lauren actually smiled. She let out a laugh.

“Like a date?” I grinned. I nodded. She kept the smile wide. “You know I’m a lesbian, right?” I blinked at her. I should have known. Generally, I was pretty good about being able to tell these things. But not this time. I stammered some lame apology, but she laughed it off and said she took it as a compliment.

Fly, fly your thoughts...

A year passes. My grungy rock band breaks up (over a girl, of course). I decide that the life of a bartender isn’t enough for me and apply to a bunch of colleges. Every one but Brown accepts me, and having read Donna Tartt’s “The Secret History,” I choose a little liberal arts school in New England with a great financial aid package.

Over this time, Lauren and I become great friends of a kind I hadn’t had before. She became my girl-buddy. The one woman I could sit around doing shots with and discussing my various sexual exploits. We’d both slept with a few of the same women at the café, and sometimes (terrible, I know) we would compare notes. We were pretty close in the acquaintance way that co-workers can be. So by the time she threw out the bait to see if I’d bite, I already had one foot out the door. I suspect she waited until then just for that reason.

We were at the bar after another busy night in the middle of the ungodly hot summer of 1993. One by one, the other waiters left for the night. The manager was in back counting receipts, and only Lauren and I were left out front. We were shooting the shit about one thing or another when she grinned at me and said, “You know what I really want to do, Xander?”

“Another shooter?” She laughed. I nodded, and I poured.

“But also,” she waited until I leaned on the bar across from her. “I’d really like to fuck some straight boy with my strap-on.” I can only imagine what my face must have looked like. I drained my shot. Poured another.

“Really,” I milked the word for all it was worth.

“Yeah. Always have. It just seems, I don’t know, hot. If I found the right guy, I’d even let him fuck me.”

She held my eyes, making perfectly clear that the straight boy she wanted for this little experiment was me. I stared back at her, debate raging in my head. I was as far from homophobic as you could be. I had even had a gay experience or two, but there’s this social taboo about a macho guy taking it up the butt. All the same, the stirring in my black trousers was really all the answer I needed.

Besides, Lauren was a friend. And I still thought she was attractive. And a good bartender wants to make the customer happy.

“You know,” I said, “that sounds like it could be interesting. Especially if a nice dinner and a lot of wine were involved.” Lauren laughed, and we finally made a date for our next mutual night off at her place.

The dinner was nice. I’ve never liked seafood much, but Lauren made this dish with mussels, garlic, and white wine that was out of this world. We laughed and talked all through the meal just like a regular date. And drank, much more than her. First a cocktail, then a bottle and a half of wine. Then another cocktail. I was getting trashed. And desperately horny.

Lauren was wearing an outfit as close to sexy as she ever came. Tailored black slacks, a diaphanous shirt that was mildly see-through. I could make out her breasts through the pale fabric— small, steel hoops pierced each nipple. More interesting, her underarms were completely unshaved, bushy, and dark hair clearly apparent. Somehow, the violation of this social taboo was a massive turn-on.

When dinner was done, her demeanor changed. She sat close to me as we drank, her leg brushing against mine (bringing a pleasurable reaction along with it below my belt). Still, when she bit her lip and said we should move to the couch, a rush of fear dropped into my stomach. I remembered what was coming, and it scared me.

Lauren took my hand and led me across her Spartan apartment. The hardwood floors creaked under my feet, and it seemed that time had somehow slowed. Her couch was red, and she released my hand as she approached it. She flipped on the stereo— the Cocteau Twins— then moved to the coffee table where a black sheet sat folded. She turned to me and smiled as she flipped it in the air, unfurling it. My heart pumped faster as it drifted down over the couch.

“You sure you want to do this?” she asked. I wasn’t sure, but that lack of certainty turned me on even more. Her eyes flicked down to my pants and up again— she could see it.

“Hey,” I said. “You made dinner. I owe you something.” I grinned at her, and Lauren plunked down on the couch. She twirled her finger in the air.

“Why don’t you take your clothes off?” she asked, but it wasn’t really a question. I took a deep breath. She was in charge, something of a reversal from my usual encounter. I pulled off my black T-shirt, unzipped my jeans, and kicked off my shoes. She watched with glistening eyes. When I was finally nude, she said, “Dicks are so funny.”

“Been a while?” I asked. She patted the couch beside her, gesturing me to sit.

“Along while,” she answered. I came over and sat, my erection bobbing almost comically. I saw what was under the sheet on the coffee table: a tube of KY Jelly. I stared at it and felt what I can only describe as a hot flash, my face growing warm with dread and excitement.

Lauren leaned forward and looked at me. Silently, she ran her hand over my chest, letting the hair run between her lithe fingers. It was hot, a single fan in the window serving as the only coolant in the room. Keeping her fingers moving over my chest, she leaned in and kissed me hard. Almost too hard. She pressed her lips into my own, her tongue darting in. I tasted wine and cigarettes. I reached up to run my hands over her body, when she pulled back with a laugh.

“Stubbly,” she said, and it occurred to me that most of the people she kissed didn’t have a five o’clock shadow or a soul patch at the base of their lips. I stroked the soft hair under her arms in response.

“Uh-huh,” I answered. She smiled, took her shirt off, and said, “See for yourself.” She raised her arm, and I leaned in, licking the thick, bushy hair. I’d never been with a woman with thick hair before, and I devoured her like I was going down. She seemed to like it, her breathing growing labored, and her hands stroking my chest, my back, my legs.

I moved around to her tiny breasts. The nipples were hard and dark, and I took one of the hoops in my teeth and pulled lightly. She responded with a moan like a purr and told me to bite harder. I was happy to comply, especially when her hand found my cock.

She pulled on it awkwardly, out of practice, but it still felt good. I moved downward from her breast, licking and biting. She released my dick and pulled my face to her other nipple. “Not yet,” she said, so I tugged on the other piercing. Licked and bit until it was as hard as its twin.

Lauren raised her far arm, and I strained forward to devour it as I had the other. “Ride me,” she commanded. I climbed astride her, the opposite position from the way I usually was in a situation like this. I straddled her thighs as I licked her underarm. She smelled faintly of sweat and Ivory soap - 99 and 44 one hundredths percent pure - and grew very aware of a pressure against my ass. I moved back to her mouth. Kissed her hard.

“Is that a banana in your pocket, or are you just happy to see me?” I asked. She reached down and pulled on my cock, smiling.

“Mmm-hmm,” she whispered. “Wanna see?” I wasn’t sure if I did, but I scooted back on toward her knees nonetheless. Reaching down to her trousers, I unbuckled the belt. Unbuttoned the pants, smiling nervously. I was so nervous that my cock began to dwindle despite her awkward attentions. I unzipped her pants.

 
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