by Rachel James
I met Isaac a few years ago at the end of August of 2019. We had an incredible first date and ended up seeing each other casually for a little while. I really liked him. Really, really liked him. So I got up the courage to ask if he’d be interested in spending more time together and doing date-type things, rather than just hooking up. He said he liked me too, but that he had actually just decided to exclusively date someone else. That was sad for me.
We texted a few times as friends after he turned me down, but this eventually petered out. He moved away from my city and we lost touch. I wistfully visited his social media pages and fantasized about him and how it felt when we were sleeping together.
Then, in January of 2022, he texted me saying that he’d be in town for the weekend to visit, and asked if I wanted to do something. A euphoric satisfaction overtook me when I got this message. He texted me after not speaking for over two years! He remembered me, he was still interested, he still felt some sort of connection! I told him I’d love to get together during his visit. We made plans for him to come over to my place and bring takeout for lunch. I felt giddy. I got my hopes up – way up. I knew it would be healthier for me to temper my expectations. He could have still had a girlfriend, for all I knew. Maybe I was just one stop of many as he made the rounds seeing all of his different friends in the area. Were we friends? I didn’t know.
I grew more and more anxious as the day crept closer. I felt so scared that he would show up and just be a platonic pal with a girlfriend and no attraction to me anymore, or that he wouldn’t come at all. Part of me didn’t believe he’d be there.
Isaac arrived with a paper bag in hand and cheeks red from the cold. We hugged hello, which I thought maybe was a good sign. I offered him water, we sat down at the table, unwrapped our food, and ate while we had a catching up chat. Mid-sandwich, I asked if he was dating anyone. He said no. Exclamation points flashed in my head. A little bit later, he shifted in his chair and I felt his foot come to rest gently on top of mine. The knots in my stomach started to feel more like butterflies. We talked some more. And then he stood up, leaned over, and kissed me.
Relief and excitement coursed through my veins. A triumphant thought struck me – I was right! I was right that his interest in me still included this type of intimacy. I kissed him back and then rose from my chair and put my arms around him. Urgency drove our movements. I could feel it in the way he touched my waist, pulled me close, and caressed my tongue with his.
“I’m sorry my hands are cold,” he said breathlessly.
“It’s okay, sorry mine are too,” I said. We made our way over to the couch. I sat next to him and pulled a blanket over us to block the chilly air emanating from the window, but it slid off to the side when I moved to sit on his lap, straddling him. He ran his hands over my tits and my hips and thrusted forward so I could feel his hardening cock. I rested my full weight on him, letting gravity help me get our bodies closer together. He grabbed my ass before slipping his hands under my shirt. I kissed his jaw, nudging his head to the side so I could lavish kisses on the left side of his neck, then the right. He suggested we head to my bedroom and I agreed.
My room was cold – I lived in a drafty old house, plus it was about fifteen degrees outside. We got under the covers only to get out of them a moment later to undress, except for our socks. I turned to lay on my side so we could spoon. He hugged my body tightly against his, with one arm around my chest and the other between my legs. I gasped when I felt him touch me there. His fingers spread my sensitive lips apart so he could rub my clit. I opened my legs slightly to give him better access. He moved his fingers a little lower and began sliding one inside me, quite easily since I was so wet and wanting. I moaned at how incredible it felt. His warm chest against my back, his cock pressed against my ass, his careful teasing of my pussy. He thrusted his fingers faster and harder, but I begged him to go slower and softer, so he did.
He regretfully mentioned that he didn’t have a condom with him. I assured him that I had some on hand and leaned over to my nightstand to grab the little basket I kept there. I handed it to him and he put a condom on. I kissed his chest and thighs, admiring his body, until he had me turn over again to resume spooning. He took his cock in his hand and guided it into my waiting hole. I arched my back so we could find the best angle. We both moaned as he slid into me. I gloried in the feeling of fullness. He used one hand to touch my clit again, intensifying the sensations. And that’s when he started whispering the perfect words in my ear.
“I thought about you,” he said softly.
“You did?” I whimpered. Hearing him say that made me feel unbelievably desired. I melted. “I thought about you too.”
“Yeah, I did. I thought about how sexy you are,” Isaac continued. “I thought about you, that time I was inside you just like this. Fucking you from behind while we read erotica together. Fantasizing…”
“Fuck, yes, that was hot.”
“And imagine how fucking hot it would be if we were out in a bar or something. And pretended we were strangers and didn’t know each other. And we started talking, and flirting, and getting even more flirty. And I put my hand on your leg, slowly sliding my hand up your thigh. And I can’t take my eyes off of you and your huge fucking tits. And then we sneak into the bathroom together so no one sees us. I’d turn you around so I can fuck you from behind. And we don’t even take our clothes off, you just pull your pants down a little bit, and I have to put my hand over your mouth so no one hears you…”
“Ohmygod. Fuck. I’d really like that,” I said, panting and thrusting my hips to match his pace. I inwardly marveled at how he was able to spin that little fantasy on the spot, that he was confident enough to say the word flirty while we fucked.
“Good,” he whispered, satisfied at the effect of his words. “How do you want me?”
“I want to ride you,” I told him. He deliberately pulled out of me and we repositioned ourselves on the bed. He laid down and I got on top. We shared a deep kiss, and then I stroked his cock a few times before rubbing the tip against my clit and sinking down so he was inside my wet cunt again, where he belonged. He ran his hands through my hair and down my back. My eyes shut for a moment while I savored the feeling. When they fluttered open, I met his gaze and took in how pleasure played out across his face. He asked me to slow down a few times because he didn’t want to come quite yet. I didn’t love sitting straight up in this position, but I did it when he prompted me to. His eyes feasted on my soft, bouncing tits. He reached forward to touch and tease them.
Our eyes met as he slowly trailed his hand further up my chest until coming to rest at my collarbone. I grabbed his wrist as a way to tell him that that was as far as I wanted his hand to go. For once I actually found it hot to do a fantasy choke. Just having his hand near my throat without his fingers going around my neck let me enjoy the thrill and turned me on. After a few moments, I tugged his hand away so I could lean down to kiss him again and feel our bodies pressed together.
I rode him until I admitted I was tired. Again, he asked me how I wanted him, so I said I wanted him to be on top this time. He eagerly obliged. I touched his lovely chest, back, and shoulders as he kneeled between my legs. He thrusted into me deeply and firmly. I wrapped my legs around him to draw his body closer to mine. He kissed my neck, my ears, even my arms, as if he couldn’t get enough of me. I told him how good it felt. I bent my knees more and he pushed them toward my shoulders so he could fuck me even deeper.
“Is this too much for you?” he asked.
“No, it’s not too much. I like it.”
I gasped when he pulled almost all the way out and then slid his hard cock all the way in, as far as I could take him. At this point we’d been at it for quite a while. He was getting close to coming, and I told him that I probably wasn’t going to come. I could always get myself off, but it was normal for me to have difficulty coming with someone else. We resumed spooning and he fucked me hard, squeezing my tits and grabbing my ass until he came. Isaac held me for a while before slipping his soft cock out of my cunt. He threw the condom out and we cuddled up under the blankets again.
Snuggles, back rubs, and sweet kisses eventually escalated. He teased my clit with his fingers, rubbing and stroking me until I became a needy mess. I gently ran a finger across his lips before slipping it into his mouth. It felt tantalizingly good to feel him sucking and licking me. I added some more lube to my cunt, stroking it gently along my opening. I took his hardening cock in my hand with a firm grasp and stroked him until he was ready to enter me again.
“It feels so good when you touch me like that,” he moaned quietly.
He put on another condom and pushed slowly until he filled my pussy. This time I reached for a vibrator to use on myself while he took me from behind.
“I feel so close to you,” he whispered in my ear. My pussy clenched and quivered to the brink of orgasm, and I told him I was close, but I didn’t manage to come. I got on top and he sucked my nipples while I rode him. He pulled my ass cheeks slightly apart from one another, making me feel more sensitive and exposed. We kissed, mouths open, and I nipped his bottom lip, then pressed my face to his neck. He put his arms around me and held me down while he pounded into my wet cunt.
Then we switched. Again, he pushed my knees toward my shoulders so he could fuck me as deeply as he possibly could. I knew my belly turned into a bunch of rolls squished together in this position. But I managed to set that thought aside as soon as it appeared. Why should I care about that when I was having such a fun time? Isaac sprinkled kisses on any part of my body he could reach. He kissed my leg, which for some reason made me melt. I ran my fingers through his hair and dug my nails into his shoulders, whimpering.
“You’re so fucking sexy,” he groaned, leaning down to suck on my nipples.
“Mmm, so are you.” I was too distracted to think of an original compliment.
“I’m getting close to coming,” Isaac added, continuing to lavish attention on my tits. “Would you – would you mind if I come on your tits?”
“Not at all! You want to fuck them?” I offered, though I already knew what his answer would be.
“Fuck, yes,” he answered immediately. I liked how excited he was. Having my tits fucked didn’t do a ton for me in terms of physical sensation, but I still found it fun. Not everyone has tits big enough to completely envelope a cock as it slides between them, but I do. A sweet thrill of accomplishment and eroticism, and the satisfaction of fulfilling someone’s specific desire, was plenty for me to enjoy.
Isaac reached over to the nightstand to grab the bottle of lube. He rubbed some on his cock and on the inner valley of my chest. With his knees on either side of my waist, I pushed my tits together so he could slide his cock between them. He moaned with pleasure and thrusted back and forth. The soft, pillowy embrace quickly brought him to the edge. He came copiously all over my chest and my face.
“You like that, huh?” I asked, teasing.
“I didn’t think there would be so much. Sorry about that,” he said.
“It’s okay!” I said. I handed him a tissue and he used it to wipe his cum off of my face and my body.
“Wow. I’m dead right now.” He collapsed next to me on the bed and closed his eyes. I laid my head on his chest and we wrapped our arms around each other. Our body heat sealed the gaps between us, laying full and warm and close. My belly felt completely devoid of the usual twisting knots. It stayed still and peaceful for once as my anxiety faded all the way into the background. I felt so safe and comfortable, in fact, that I fell asleep. I had no idea how long we napped, but the next thing I knew, we woke up in exactly the same position. We stretched and stayed under the cozy blankets, snuggling and talking for a while. He was easy to talk to.
“I think I have to go soon,” he said eventually.
“Aw,” I pouted. I hugged him and draped my leg across his body to hold him down. I wished he didn’t have to leave, but he had plans to meet other friends for dinner. We got out of bed and dressed quickly since it was so cold.
At the door, once he had his hat, coat, and shoes on, we said our goodbyes. Isaac told me to let him know if I was ever up in Boston; I told him to let me know if he was ever back in Philly. We hugged and he stepped out into the brisk evening.
A sense of melancholy washed over me. I’d had such a dreamy afternoon of good food, good sex, and good company, but it was over, and I didn’t know if I would ever see him again. I wanted to. I liked him. I turned our encounter over and over in my mind’s eye, wondering about the meaning of each touch, each word, though I knew I was completely overthinking it. Were the sweet things he said to me real? Had he really thought about me? Or was it just an empty phrase uttered in the heat of the moment?
Much to my relief, he texted me several hours later saying that he had a great time. I felt a glow of pleasure join my chaotic mess of insecurities and sadness. I told him that I had a great time too. And then I simply couldn’t help myself. I had to voice the question I’d been asking myself since he left.
Did you really think about me?
He said yes, he had thought about me. I believed him.