I was back in Montreal for Christmas. As I drove around the city I couldn’t help but enjoy old memories. Maybe because of the season, one memory from a Christmas past stood out. Swinging a little out of my way I drove past the old grey stone building where a long-time friend and I were once roommates. Her name was Sheri and we’d known each other since we were kids.
It was just before Christmas and for once Sheri and I had the apartment to ourselves. We’d been secretly sleeping together for a few months and it was a rarity for the two of us to be completely alone.
When we first slept together I had been seeing someone else. That was the main reason we kept things secret, but there were other reasons too. I did break things off with the girl I was seeing once I realized I couldn’t resist sex with Sheri. So, while the main reason for secrecy was out of the way, we still kept things to ourselves. Among the remaining reasons for secrecy was that we were kind of finding it fun to sneak around.
We didn’t even let our other roommates know. Since at least one of them was usually home, a certain amount of subterfuge was required. As luck would have it the balcony off my room also led to a window opening to Sheri’s room. We could say our good-nights and head to our rooms. Then I would just step outside and climb through Sheri’s window.
On this occasion, both roommates were home visiting their parents. The night before our roommates left for the holidays we had a gift exchange. I’d suggested to my other roommates that we get Sheri lingerie. They both thought it would be funny. I thought it would be even funnier, because I knew that I’d see her wearing them.
That was two nights earlier and now the two of us were lounging in the living room enjoying a late morning coffee. I had on a pair of boxers and Sheri had on a big yellow sweatshirt with a number on it. It looked like an oversized football jersey.
We fucked in the living room the night before. It was the first time we had been able to do it in there since the night it had started between us. We had begun on the couch and slowly peeled our clothes off. I went down on Sheri’s blond pussy before crawling up to fuck her. The next stop after was the bathtub, where I shaved her pussy clean. Afterwards, in Sheri’s room, she put on her purple Christmas present for me. She looked so good in it too, especially sucking my cock. Then it was my turn again. Going back down her, I undid the snaps between her legs and licked her baby smooth snatch.
Sheri always liked having her pussy licked. After all, what girl wouldn’t. Her newly shaved pussy seemed to give her enjoyment a fresh intensity.
After a while I turned Sheri over and ran my tongue over her asshole. I softly circled her rim with my tongue before plunging as deeply as I could into her ass. She liked that a lot too. When I climbed back up on Sheri my cock slid with ease into her pussy. So far, she liked everything I did to her.
When I started fingering her ass Sheri was pretty good with that too. When I pulled my cock back from her pussy and pressed it against her virgin ass, that's when Sheri paused, “Um, what are you doing?”
Another reason we kept things secret was that Sheri’s best friend was a recent ex of mine. I had introduced her friend to anal and considering how close they were, I felt pretty sure that information would have been shared. It seemed unlikely that Sheri would have been surprised when I finally tried her ass too.
“I think you know,” I said.
“Alright, but just go slow,” Sheri warned.
My cock was slick with Sheri’s pussy juice and even though her body was tense I still managed to work my way into her ass. I couldn’t fuck her hard, but there is always something subversively exhilarating about thrusting into a body that’s so resistant. Despite the restrictive dynamics, or maybe because of them, the excitement had me quickly filling Sheri’s ass with its first load of cum.
When Sheri asked me afterward what exactly it was that I liked about anal sex anyway, I knew that I’d yet to make a convert.
The next day we lazed around the apartment. Having the place to ourselves, we sat in our living room and enjoyed a late morning coffee. Not only were our roommates gone, but with all the snow our normally busy street was silenced by both the weather and holiday season.
We chatted about how we were going to get to our parents’ places for Christmas. We kissed, talked about the night before and decided to put off the bus ride for one more day. Since we had the apartment to ourselves we might as well use it.
Eventfully Sheri fished my cock out of my boxers as we talked. It began as nonchalant fondling, but slowly became more purposeful until Sheri had a stiff cock in her hand.
Suddenly stopping, Sheri got up and said she’d be right back. She walked down the hall to the bathroom. I could hear her rooting around and after a moment Sheri re-emerged with a jar of Vaseline.
When she got back to the couch Sheri told me to take off my underwear and lay back. I liked where things seemed to be going, but Sheri had a look on her face that gave me some pause for concern. She was up to something, but as long as my cock was part of the plan I was willing to play along.
Our couch was a futon without armrests. Sheri positioned herself at its end on the floor between my legs. She began by stroking my cock, which was already fully hard in her hand. Smiling at me, Sheri would nuzzle her face against my shaft, licking my naked head and taking it in her mouth. It was so nice in the peace and quiet of our apartment to be enjoying such an intimate blowjob.
Out of sight at the foot of the couch, I could hear Sheri fussing with the lid of Vaseline jar. While lubricants weren’t my preference, having my lover take the initiative was a welcome treat.
When Sheri’s other hand joined the action, the application of lube didn’t match my anticipated target. “Um, what do you think you’re doing?” I asked.
“Since you like putting your thing in my bum so much, I thought you would like to know what it feels like.”
“Yeah, I don’t think so,” I declared.
“What!” Sheri exclaimed. “Why not?”
“That’s for out only,” I pointed out.
Showing a little pique Sheri snorted, “You’re kidding, right? I’ll remind you that the next time you want to fuck my ass.”
“It’s different, you’re a girl,” I argued, realizing that I was grasping at straws.
“What do you think? That you’re gay if something goes up your ass?” Sheri teased.
“No, that’s not it…” I lied
Realizing the weakness of my position and especially not wanting to jeopardize future access to Sheri’s ass I surrendered.
Laying back looking up at the ceiling I tried to relax. When I felt the cool chill of Sheri’s gel-coated finger against my back door, I couldn’t help but tense up.
“Relax ya big baby,” Sheri chided.
“I’m trying,” I said, hopefully not sounding too defensive.
With the muscles around my asshole tightening, Sheri worked her finger into my butt. Her other hand stroked my cock, helping to ease my reluctance.
I wouldn’t have described the initial feeling as pleasurable. I just had to try to embrace the thrill of an imaginative girl doing something unusual to me.
Sheri eventually managed to get her finger all the way in. She was gently fingering my ass while stroking and sucking my cock. The more comfortable I became with Sheri’s finger in my ass, the more I realized that I was kind of liking it. Really liking it.
When I spread my legs wider and put a foot up top on the backrest of the couch, Sheri sweetly asked, “Would you like to try two fingers?”
“Yes,” I moaned.
Withdrawing her finger Sheri reached for the jar at her knees. Retrieving a big dollop of lube, she smeared my asshole. Then she reached down again scooping another glob to coat her index finger and middle finger. This time my ass still felt tight, but I wasn’t tense at all. I loved the feeling of her fingers filling my ass.
Sheri was doing an admirable job stroking my cock and finger fucking my ass. She might not have been in perfect sync, but it was still a great multi-tasking job. When her cock stroking hand needed a rest, Sheri would take a break and suck my cock.
Eventually I had to ask, “Can you try to put one more finger in?”
“Really! I’ll try,” Sheri agreed.
Sheri pulled out, added a little more lube to her fingers and worked three of them up my ass. It felt incredible. My asshole felt so stretched and my cock so swollen. Once my ass became accustomed to one more finger Sheri began fucking my ass again.
“Just squeeze my cock and do my ass,” I directed.
Sheri tightened her grip and while slower, continued to stroke my cock. The feeling was unimaginable. Having my cock pumped while my ass was being fucked began feeling like a little too much. I wanted to really savour the sensation and even the minimal touch of Sheri’s hand on my cock felt overwhelming. I was having a little trouble verbalizing any guidance though. Before I reached the point of no return, I reached down with both hands to steady Sheri’s hand on my cock. When I felt my orgasm back off, I began guiding Sheri’s hand slowly up and down my cock again.
Then once again I asked, “Can you try one more finger?”
“Wow, you really like this don’t you?” Sheri teased.
“I do,” I confessed.
With that, Sheri lubed up her hand a little more and began working all four fingers up my ass. I squeezed my cock in Sheri's grasp and it felt so good.
“Deeper,” I urged.
“I can’t get my hand in any deeper. I don’t want to hurt you and I’m already almost up to my knuckles,” Sheri advised.
“Don’t worry it doesn’t hurt,” I said.
“I don’t know, I don’t think I’m not strong enough to use four anyway. It’s really hard and I can actually get deeper with three,” Sheri confided.
I suppose that three did feel better. Maybe it was because Sheri could actually fuck my ass without engaging in a feat of strength and endurance.
“Okay, do three,” I agreed and again left my cock to Sheri’s hand.
The finger debate had the benefit of backing off the orgasm that I felt was right on the brink.
Sheri applied a little more lube, even though my ass already seemed fully greased. She went back to fingering my ass, stroking my shaft and occasionally taking my cock in her mouth. I loved looking down at Sheri between my legs, seeing her pump my cock right in front of her face. With Sheri’s fingers deep in my ass, it was like nothing I’d ever felt before.
As the sensations built every so often I’d weakly direct, “Slow, slow…”
Once more I steadied Sheri’s grasp of my cock. I pressed Sheri’s hand down to the base of my shaft, making her pull my flesh back as tight as possible. Eventually even Sheri’s hold on my cock was overstimulating me. Wordlessly I pushed away Sheri’s hand. When I did Sheri also paused fingering my ass. I knew that I was beyond the point of no return and that all I needed was to have Sheri fuck my ass.
“Oh, fuck my ass!” I demanded.
My legs were spread apart and my untouched cock twitched at attention. Sheri began pumping her fingers in and out of my ass. They were long deep strokes that built in intensity. My eyes were vision-less slits and my head fell back on the couch. I could feel my orgasm welling.
When I came it was like no orgasm I’d ever had before or since. Orgasms are wonderful in all situations, but my body had never been so completely given over. I’d always been used to the feeling of an orgasm being centered in my genitals, but this was something more. It wasn’t just concentrated in my cock and balls at all. I felt it deep in my core and it radiated throughout my body. My juices didn’t just shoot from my cock either, they blasted. My untended cock erupted without touch, sending sperm flying. It arched through the air landing on my shoulder, grazing my cheek and getting in my hair. A white briny splash hit the couch beside my head where it soaked into the fabric. With the deep intensity of my orgasm, I didn’t realize the effects of those first unbelievable shots until my awareness returned. Then with surprise, I realized the source of the wet sensations on my skin.
I might have cum unduly quick on occasion, but I’d never cum before without at least some contact with my cock. The orgasm didn’t seem to want to stop and I could feel the ooze from my cock spreading over my stomach.
Even Sheri looked stunned by what she saw. When the orgasm seemed near its end she pulled her fingers from my contracting ass.
“Wow, that’s a lot of cum Mike,” she said running her hands through my cream.
I reached down to touch my cock. I wanted to milk whatever remaining sperm and sensation I could. Taking my still hard shaft in my hand I slowly stroked myself, while Sheri massaged my cum into my stomach and chest. It felt so good until I tried to feel my balls. I was shocked to find that they were gone.
Stunned at the damage I’d done to myself, I reached down with my other hand to confirm. With panic in my voice, I asked Sheri, “What happened to my balls?”
It was only when I stood that my nuts slowly returned. With my orgasm they had contracted completely inside of me. I’d never experienced anything like that before. I wish I had, because instead of panicking over the damage I thought done to me though anal manipulations, I could have instead just enjoyed the resulting sensations.
Once the crisis was over and most of the laughs at my expense had passed, Sheri and I returned to our enjoyment. Not only were we able to make sure that I had no lasting impairment, but Sheri was also much more accommodating when I repaid her in kind.
