“Do you want to have sex?”
Those were the words that started my sexual relationship with Jill. We were in the middle of a chess match, both lamenting our uninspired love lives. Jill’s question shocked me, mostly because her tone was so casual.
Two months prior, I was at a house party in South Tampa. A mutual friend introduced Jill and I and we struck up a conversation. At twenty-four years old, Jill was exactly my age. She was of average height and build, with chestnut-colored shoulder-length hair and big brown eyes.
Jill and I talked for quite a while. We were both chess fanatics and enjoyed watching The X Files every Friday night.
Jill was charming and a great conversationalist but I didn’t find her particularly attractive. At the time, I wasn’t interested in anyone romantically, having just gone through a breakup with a longtime partner.
Still, the conversation was light and fun. Jill and I made plans to get together the following Friday night, watch the new episode of the X Files, and play some chess. The intent was strictly platonic. Jill made it very clear that she was also uninterested in romance.
Every Friday night for two months, Jill and I hung out at her apartment. We watched the X files, played chess, enjoyed a few laughs, and I went on my merry way.
Then, on a random Friday night, without any forewarning whatsoever, Jill blurted out, “Do you want to have sex?”
Jill’s question hung in the air. Her big brown eyes staring into mine as she patiently waited for an answer, as though she’d merely asked whether I wanted to order a pizza.
“I’m confused,” I finally answered. “Neither of us want a relationship, right?”
“I didn’t ask to be in a relationship. I asked if you wanted to have sex.” My face must have revealed a mix of skepticism and confusion. Jill continued, “Nick, I’m horny. I’m asking if you want to have sex because I trust you.”
The proposition was intriguing. The thought of entering into a purely sexual relationship had never occurred to me until that moment. A friends-with-benefits scenario seemed like the quest for the Holy Grail - good intentions doomed to fail. Yet, something about Jill made me believe it could work.
Jill and I spent the next hour in negotiations. After agreeing on the rules of engagement, we awkwardly shared our first kiss. Jill was an incredible kisser with full lips that immediately kindled my desire. Our awkwardness quickly transformed into unbridled lust.
As I sat on the sofa, Jill stood above me and seductively lifted her t-shirt until her perky, grapefruit-sized breasts spilled out, puffy nipples fully erect. Jill smirked as she slid her Levis off her curvy hips. She took a step forward and slid her nude body between my legs. Her skin was flawless from head to toe. Then Jill took me by the hand and said, “Let’s take a shower.”
Other than a little making out, the shower was all about getting clean. After drying off, we made our way to Jill’s bed and got down to business.
Jill guided me onto my back and got comfortable between my legs before firmly grabbing the base of my cock. She smiled and said, “You have a nice cock,” before licking it from bottom to top.
Jill stared into my eyes as she joyfully played with my cock, teasing the head with her tongue and lips. After a few minutes of oral attention, Jill said, “Now I want you to massage my body. I’ll tell you how I like it.”
Tell me, she did. Apparently, Jill once took a tantra massage class and was eager to impart her knowledge. Jill knew exactly what she liked and expressed her desire without limitation.
I was surprised to discover how much massaging her body turned me on. Jill was specific and clear as she directed my hands on a tour of her legs, feet, back, front, head, arms, fingers, toes, hips, breasts, and everything in between.
Eventually, the tour led to Jill’s pussy. Her vulva was plump, the delicate folds and creases of Jill’s thick labia protruding from her slit. Clean-shaven, except for a small tuft of hair an inch above her swollen clit.
Jill’s clit was unusual and something special. It was much larger than any clit I’ve ever seen. Jill taught me how to massage it. Delicately rubbing my fingertips around the perimeter before tapping it repeatedly. Her hips involuntarily began to gyrate as she growled with delight.
Jill demanded my mouth. Without hesitation I pulled her clit in between my lips and gently sucked. She propped her feet on my shoulders, her hands desperately clutching at handfuls of bed sheet. When I stuck my tongue inside of her, Jill giggled and offered words of encouragement.
My face soaked in Jill’s juices, she said, “Now rub your cock on my clit.”
After positioning myself in between Jill’s legs, I gripped my cock and teased her clit with the head. A thick bead of pre-cum oozed out. Jill scooped it up with her fingertip and brought it to her mouth for a taste.
Then I slipped inside of her. Slowly and deliberately filling Jill’s tight pussy with all seven inches of my hard cock, until the head was pressing against her cervix. She clenched her kegel muscles and laughed with joy as her neck and face flushed red.
The first wave of a massive orgasm began to crest in my abdomen and I realized that I had no chance of stopping it. Jill sensed it and said, “Cum all over my body.”
The first blast of cum flew above Jill’s head and slammed into her headboard. Her eyes widened and her face lit up with a smile just as the second blast fell on her cheek and neck. The rest covered her breasts and stomach. At the time, it was the best orgasm I’d ever had.
When the last wave crested, Jill said, “Put it back in my pussy and hold still.”
After sliding back inside of Jill’s body, I remained motionless. As my cock went into a semi-hard state, Jill rhythmically squeezed her kegel muscles. In less than a minute, my cock was fully hard again.
Jill flashed a devilish grin and said, “Fuck me.”
Astounded by my sudden stamina, I did exactly as commanded. Pinning Jill’s legs to the bed with my hands, I did my best to put on a show. Jill's eyes were fixated on my cock as it slowly emerged from her pussy only to disappear again. Taking my time, I increased my pace until my hips were pounding against hers.
Jill squeezed her own nipples as her body started to spasm. The look on her face was pure joy. As Jill reached the crescendo of her orgasm she begged for me to cum inside of her. It took no effort to oblige. Coming at the same time as Jill was especially erotic and sensual.
We collapsed in a heap but were far from done.
Over the next six months, our sex life only got better. There was something entirely liberating about our arrangement. Without the romantic entanglements, Jill and I were free to be entirely honest with each other about our turn-ons, turn-offs, and everything in between.
Sex with Jill was also fun. She smiled and giggled throughout our encounters and always let me know when I was making her feel good with purrs, moans, and praise.
The way we talked, laughed, and joked around was no different than if we were playing chess. If Jill wanted me to eat her pussy, she said, “I want you to eat my pussy.” If I wanted Jill to ride my cock until I came, I simply said, “Fuck me until I come.”
As a result of our lighthearted honesty, we experienced something very rare - an entirely fulfilling sexual relationship. We knew how to tease one another and how to get each other off. Our sex often lasted for hours. On my days off work, I would come over to Jill’s house early in the morning so that we could hang out, watch TV, and fuck well into the night. If I got horny at any time and she was home, Jill made time for me and I did the same for her.
Our number-one rule was that we remained monogamous, so that we could forego condoms (Jill was on the pill). If either of us had sex with another person, we were required to say so. Throughout our time together, I seldom felt any desire for another woman, so we seldom discussed the topic of other sexual partners.
With one exception.
Jill and I hung out with mutual friends on occasion, without letting on that we had anything other than a platonic friendship. Secrecy was another important part of our agreement. If either of us met someone we wanted to date, we didn’t want them to know we were already in a sexual relationship.