Benefits with Friends

James and I had not hooked up in months. While we stayed in touch, messaging fairly regularly, his depression was at an all-time high, which killed his sex drive. There were a few sporadic nights when he'd do some cocaine, get horny, and then message me for sexting, but any time I invited him to come over and offered to make him feel better, he didn't feel up to it. To be fair, driving while coked up was not a good idea, plus imbibing always made him sweat and while there was a shower at his place, using it so late at night would wake up his dad and stepmom. My hot water heater only holds about six minutes of hot water, which meant that by the time I showered there wasn't any hot water left over for anything else.

One night, we were sexting - I really wanted it. I wasn't sure why I had such a strong desire for him that night, but I suggested he come over. I told him he could shower here - we could shower together if he wanted - and then he could just lay back and let me work my oral magic on him. The more we talked, the more open he got to the situation; he confessed that he wanted to jerk me off, to suck me - he wanted to make me cum. While my main goal was to make him cum, I certainly wouldn't say no to reciprocation.

It was after three AM when James decided to come over and showed up at close to four o'clock. I'd showered a while before that - there would be plenty of hot water for him to clean up before we got lost in each other's body. During a few of our late-night sexy conversations, he'd mentioned that he fantasized about me opening the door for him wearing only my robe; once he was inside, he'd get down on his knees and start sucking me off. I asked him if he wanted me to wear the robe for him - he said yes.

I let him in, glad to see him. While I enjoyed the sexual aspect of our friendship, I did genuinely like James as a person; he could be an asshole at times, but really, who couldn't? He asked me to get the shower warmed up as he started stripping down in the darkness. I asked if he wanted to shower solo or if we were going to try showering together like we'd talked about a few times; he wanted to shower together.

I let him in first, and then stepped in behind him, towering over his short frame. I squirted some body wash into my hand, then lathered up and started stroking his soft cock; almost immediately, he stopped moving and a small moan escaped his lips. He reached down to touch mine - already growing hard. As he lathered more body wash into his close-cropped hair, my soapy hands rubbed all over his body, still in disbelief that this was happening, that the guy I had once fantasized about dating - but was tragically straight - was naked in my shower with me.

James leaned down and started sucking my dick; it wasn't bad head - quite decent for a beginner. I wanted to thrust my hips, to fuck his mouth, but I didn't want to overdo it - he was new at this and I wasn't entirely sure what his limits were yet. I got incredibly turned on when he grabbed me, turned me around, and then stood flush against me - his dick against my ass - while he jerked my cock. I had told him that I thought it was hot when he took charge - it was even hotter that he was trying to make it pleasurable for me as well.

We moved to the bed, huddling under the blanket together as the cold air hit our damp skin. I turned my space heater on to max heat, shivering against the late night chill. Immediately, I felt his hand move over my hip to my cock, eager to make me spill my seed. "I want you to cum on me," he said, his voice quivering with excitement.

"Where?" I replied, reaching around and caressing his back.

"On my chest or on my face."

"Okay."

He leaned over and started sucking on my nipple - my weakness. I loved how open he was being, how intuned to my desires. Maybe it was the years of anticipation, the acceptance that it would never happen that made it so hot when reality seemed to no longer exist and what had seemed impossible was suddenly happening.

After a few minutes of us touching each other, he stopped. "I want to suck your dick, but please don't cum in my mouth - I don't think I'm ready for that."

"Of course not," I promised. I would never disrespect someone's preference for that - not on purpose.

James pulled the blanket back as he took me in his mouth, slowing moving up and down - it felt good. I watched his head bob on my cock, biting my lip. James wasn't incredibly hot, but something about him did it for me. My right hand explored his body, pinching his nipples, caressing his tattoos, rubbing his pronounced ears, raking through his short hair. I wished I had a vagina in that moment - the idea of his head between my legs, eating me out made me incredibly horny. I knew that he would be more comfortable with that scenario and he'd be more likely to fuck me that way.

After a couple of minutes, he came up for air. "Where's that lube?" he asked, breathless. I casually reached over to the nightstand and grabbed the bottle. I drizzled some in his palm, watching with delight as he slicked his hand up and then started jerking me off. I purposely saved lube for special occasions, so that it would be a luxury; as James stroked me, I couldn't help but close my eyes and rest back against the pillow. My desire for him continued to grow; I wanted him so badly.

James alternated between his hand and his mouth for a few minutes before he stopped and moved up to hover over my body - his arms clasping the metal frame of my headboard as his hard cock dangled in front of my mouth. Without provocation, I opened my mouth and took him inside, reveling when he sighed with pleasure. James's cock wasn't huge, but for me it was the perfect size: decent length and relatively thin - it didn't hurt my jaw to suck him, and I knew that if he ever did work up the courage to try to fuck me it wouldn't be an entirely painful experience.

"Okay, stop," he gasped, pulling away, "that felt too good. I don't want to cum yet. I should have cum before I came, then I'd last longer now."

"But then you wouldn't be horny right now and probably would have just stayed home," I pointed out, stroking his cock laconically.

"Yeah, you're right," he agreed, looking down at my hand on his member. "Where's that pocket pussy?"

James had never used a pocket pussy before; I'd gotten one as part of a birthday bundle from Adam & Eve a few years previously. When he'd said that he was coming over, I'd cleaned it up, hoping that I'd get the chance to use it on him.

I handed it to him and watched with delight as he slid a finger into it and moaned slightly. He quickly lubed up my cock and then started moving the stroker up and down on me, his eyes locked on it. While it felt good, I didn't want to cum from that, I wanted his hands or mouth to be what sent me over the edge.

"I really want you to cum on me," he said after a few minutes, his eyes still locked on my cock as it disappeared into the silicone vagina.

"You want me on top of you?" I asked, biting my lip again as a fresh wave of horniness washed over me.

"Yeah," he answered, practically a pant.

I eased him down onto his back and then straddled him, careful not to crush him under my weight. I reached back for his cock, holding it in place as I spread my cheeks and let it tease my hole. "Like that?"

"Yes."

I let his cock flop back down and then started grinding my hips, jerking my cock as I stared down at him. I hadn't been this turned on in a long time - it felt nice to know that with the right person my sex drive could still be strong and virile.

"I really wish I had a pussy for you," I whispered, continuing to grind on his pelvis. "I'd love to just slide you inside me and ride you until you cum deep in me."

"That would be wild." His hands worked up to my chest, squeezing my small breasts.

I reached down and started lightly choking him, grinding my hips faster as he jerked my cock. It felt so amazing - I didn't think that I was going to last much longer. "Fuck, Daddy," I panted, throwing my head back. "Fuck, James..."

I came all over his chest, quivering with pleasure as each ribbon of cum shot onto him.

In the afterglow, I got down and ran to get him a towel. I wiped my cum up, feeling no shame or discomfort. Normally, I didn't like people to see my naked body; years of frequent cannabis use had let to unwanted weight gain that, although I'd stopped using cannabis almost completely, I'd still been unable to lose. But the good thing about being intimate with James was that he didn't care about my weight, there was no pressure to look amazingly, there was no embarrassment over my extra weight.

"Want me to use the pocket pussy on you?" I asked, eager to make James finish before exhaustion set in and I lost any interest in his body.

"Sure, I've never used one before."

"You'll love it."

I squirted some lube into my hand and quickly slicked it onto his hard cock. "I've never gotten a handy with lube," he reminded me, gasping at the extra pleasurable sensation.

I lined the lips of the silicone vagina up with the head of his cock and then slowly pushed down, watching his face in anticipation. As the cap of his dick was stimulated, he sighed, his eyes rolling back a little. I grinned as I worked the stroker all the way down and then started to move it up - and down - twisting to ensure that he would experience the full effect of the inside ribbing.

James reached down and stopped my hand. "I don't want to cum yet," he said again, his voice tight.

I slowly worked the stroker off of him and set it off to the side, keeping an eye on his cock, which was flushed red from the stimulation; I knew that he wouldn't last much longer.

He moved so that he was straddling me, his dick still slick with lube; I started stroking it slowly, watching his face as he shook with pleasure. I knew that he hadn't been with a woman in years, that this was a big deal for him; I wanted James to enjoy himself to the fullest whenever we expanded our friendship into the bedroom.

As I continued to move my hand, he grew tense. "I'm gonna cum!" he gasped. I tightened my grip and moved my hand faster, grinning as he shook and exploded on my chest. Spirt after spirt of cum landed on my chest - coating my chest hair. My load had been decent - considering I'd started jerking off nightly again - but James's was impressive: thick and such a vast quanitity. I couldn't help but feel a little thrill that I had done that to him, that I had made him cum so much.

Wordlessly, I handed him the dirty towel and grinned as he wiped himself off. I loved that our messes were now mixing together, mingling in the cotton of the light blue towel. I didn't have romantic feelings for James anymore, but I still held a deep affection for him in my heart; we couldn't date - even if he wanted to it would be a terrible idea - but we could make each other feel good, use our intimate knowledge of each other to do more than comfort one another. With James I didn't feel the awkwardness that I felt with random guys from Grindr; I was able to be fully present in the moment and enjoy myself.

As James finished wiping his dick off, he started pulling his clothes back on. It was almost five in the morning by then - he had a half hour drive back home and I needed to get myself to bed so that I wouldn't be miserable when my alarm went off at one PM. We quickly said our goodbyes and then he was gone. As I climbed into bed and opened my book - waiting for my melatonin to kick in - I couldn't help but hope that we could continue to explore this new aspect of each other, that it wouldn't get weird and ruin everything we'd built over the past seven years.