I was back in Montreal for Christmas. As I drove around town, I couldn’t help but enjoy old memories. Perhaps because of the season, a memory of a Christmas past stood out. Swinging a little out of my way, I passed the old gray stone building where a longtime friend and I was once roommates. Her name was Sheri and we had known each other since we were kids.
It was just before Christmas and for once Sheri and I had the apartment for us. We had been sleeping together in secret for a few months and it was a rarity for both of us to be completely alone.
When we first slept together, I had seen someone else. That was the main reason we kept things secret, but there were other reasons as well. I broke up 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 always kept things to ourselves. Among the other reasons for the secret is that we were somehow finding it fun to sneak around.
We didn’t even let our other roommates know. As at least one of them was usually at home, a certain amount of subterfuge was needed. As luck would have the balcony of my room also led to an opening window to Sheri’s room. We could say our good nights and head to our rooms. Then I’d go out and grimace through Sheri’s window.
On this occasion, the two roommates were at home to visit their parents. The day before our roommates left for the holidays, we had an exchange of gifts. I had suggested to my other roommates that we have Sheri lingerie. They both thought it would be funny. I thought it would be even funnier, because I knew I’d see her wear them.
It was two nights earlier and now we were both lounging in the lounge 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 shirt.
We had sex in the living room the night before. It was the first time we had been able to do it there since the night it started between us. We had started on the couch and slowly took off our clothes. I got down on Sheri’s blonde pussy before crawling to fuck her. The next stop after was the bathtub, where I shaved her own. Then, in Sheri’s room, she put her purple Christmas present for me. She looked so good in her too, especially sucking my cock. Then it was my turn again. As I descended down, I unzipped the slamming between her legs and licked her baby tear ingsher inglet.
Sheri has always loved to have her licked. After all, what a girl wouldn’t be. Her newly shaved seemed to give her pleasure a new intensity.
After a while, I turned Sheri over and ran my tongue over her. I gently circled his rim with my tongue before plunging as deep as I could into his. She liked it, too. When I got back on Sheri my cock slipped with ease into her pussy. Until now, she loved everything I did to her.
When I started fingering his 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 stopped, “Um, what are you doing?”
Another reason we kept things secret was that Sheri’s best friend was one of my recent exes. I had introduced his friend to anal and given how close they were, I felt pretty sure that the information would have been shared. It seemed unlikely that Sheri would have been surprised when I finally tried her too.
“I think you know that,” I said.
“Okay, but go slowly,” Sheri warned.
My cock was smooth with Sheri’s pussy juice and even though her body was tense, I still managed to work my way up her ass. I couldn’t fuck her hard, but there’s always something subversively exhilarating about thrust in a body that’s so resilient. Despite the restrictive dynamics, or perhaps because of them, the excitement quickly filled Sheri’s with her first load of.
When Sheri later asked me what exactly i liked about anal sex anyway, I knew I didn’t have to make a convert yet.
The next day we walled around the apartment. Having the place to ourselves, we sat in our living room and enjoyed a late morning coffee. Not only have our roommates disappeared, but with all the snow our normally busy street has been silenced by the weather and the holiday season.
We discussed how we were going to get to our parents’ house for Christmas. We kissed, talked about the previous night and decided to postpone the bus ride for another day. Since we had the apartment to ourselves, we might as well use it.
Eventfully Sheri caught my dick out of my boxers as we talked. He began as nonchalant caressing, but slowly became more useful until Sheri had a stiff cock in his hand.
Suddenly, Sheri got up and said she would come back. She walked down the hallway to the bathroom. I could hear him rooting around and after a while Sheri reappeared with a jar of Vaseline.
When she came back on the couch, Sheri told me to take off my underwear and lie down. I liked where things seemed to go, but Sheri had a look on her face that gave me some pause for worry. She was up to something, but as long as my dick was part of the plan, I was ready to play along.
Our couch was a futon without armrests. Sheri positioned herself at his end on the floor between my legs. She started by stroking my cock, which was already entirely hard in her hand. Smiling at me, Sheri nuzzle his face against my tree, licking my bare head and taking it into his mouth. It was so nice in the peace and quiet of our apartment to enjoy such an intimate pipe.
Out of sight at the foot of the sofa, I could hear Sheri waving with the lid of the Vaseline jar. While lubricants were not my preference, having my lover take the initiative was a welcome treat.
When Sheri’s other hand joined the action, the lubricant application did not match my intended target. “Um, what do you think you’re doing?” I asked.
“Since you like to put your thing in my butt so much, I thought you’d like to know what that is.
“Yes, I don’t think so,” I said.
I said, “What!” Sheri exclaimed. I said, “Why not?”
“It’s just for the outside,” I said.
Show a little stitiof Sheri sting, “You’re kidding, aren’t you? I’m going to 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 straws.
“What do you think? That you’re gay if something gets up your? 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, I surrendered.
Lying on looking at the ceiling, I tried to relax. When I felt the cold of Sheri’s gel-drenuped finger against my back door, I couldn’t help but tense myself.
“Relax ya big baby,” Sheri chided.
“I’m trying,” I say, “I hope I don’t look too defensive.
With the muscles around my tightening, Sheri worked her finger in my butt. His other hand stroked my cock, helping to relieve my reluctance.
I would not have described the initial feeling as pleasant. I just had to try to kiss the thrill of an imaginative girl doing something unusual for me.
Sheri finally managed to get her finger all the way in. She gently fingered my ass by stroking and sucking on my dick. The more comfortable I got with Sheri’s finger up my, the more I realized I was a little loving it. I really like it.
When I spread my legs wider and put one foot on the back of the couch, Sheri kindly asked me, “Would you like to try two fingers?”
“Yes,” I moaned.
By removing his finger Sheri reached for the pot at his knees. Picking up a big spoonful of lubricant, she smeared my. Then she reached down again picking up another glob to coat her index finger and middle finger. This time my was still tight, but I wasn’t tense at all. I loved the feeling of his fingers filling my.
Sheri was doing an admirable job stroking my dick and my finger by lowering my ass. It may not have been perfectly synchronized, but it was still a great multitasking job. When his handcared cock needed a rest, Sheri would take a break and suck my cock.
Finally, I had to ask, “Canwill you try to put one more finger?”
“Really! I’ll try,” Sheri agreed.
Sheri pulled out, added a little more lubricant to her fingers and worked three of them in my. It was amazing. My asshole felt so tense and my dick so swollen. Once my ass got used to one more finger Sheri started fucking my ass again.
“Just squeeze my dick and do my ass,” I directed.
Sheri tightened his grip and while slower, continued to caress my cock. The feeling was unimaginable. Having my cock pumped while my ass was fucked started to feel a little too much. I really wanted to savor the sensation and even the minimal touch of Sheri’s hand on my cock felt overwhelming. I had a little trouble verbalizing any orientation though. Before reaching the point of no return, I reached down with both hands to stabilize Sheri’s hand on my cock. When I felt my orgasm recede, I began to guide 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 that isn’t it?” Sheri teased.
“That’s what I’m doing,” I confessed.
With this, Sheri lubricated his hand a little more and began to work all four fingers in my. I squeezed my dick within Sheri’s reach and he felt so good.
“Deeper,” I urged.
“I can’t get my hand in deeper. I don’t want to hurt you and I’m already almost up to my fingers,” Sheri advised.
“Don’t worry, it doesn’t hurt,” I said.
“I don’t know, I don’t think I’m strong enough to use four anyway. It’s really hard and I can really go further with three,” Sheri said.
I guess three felt better. Maybe it was because Sheri could actually fuck my ass without engaging in a feat of strength and endurance.
“Okay, do three,” I accepted and still left my cock in Sheri’s hand.
The finger debate had the advantage of backing off on the orgasm I felt was on the brink.
Sheri applied a little more lubricant, even though my already seemed completely greased. She went back to finger inge my ass, stroke the tree and sometimes take my cock in her mouth. I loved watching Sheri between my legs, seeing her pump my dick right in front of her face. With Sheri’s fingers in her, it was as if I had never felt before.
As the sensations were built from time to time, I had only weakly direct, “Slow, slow …”
Once again, I stabilized Sheri’s grip of my cock. I pressed Sheri’s hand to the base of my tree, which made him pull my flesh as tightly as possible. Eventually, even Sheri’s grip on my dick was over-stimulating me. Without words, I pushed Sheri’s hand. When I did, Sheri also paused me by fingering my. I knew 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 apart and my cock was shivering at attention. Sheri started pumping her fingers in and out of my. These were long, deep lines that built in intensity. My eyes were slits without vision and my head fell back on the couch. I could feel my orgasm well.
When I arrived, it was like no orgasm I had ever had before or since. Orgasms are wonderful in all situations, but my body had never been so completely given. I had always been used to the sensation of an orgasm being centered in my genitals, but it was something more. It wasn’t just concentrated in my dick and balls at all. I felt it in my heart and it radiated all over my body. My juice didn’t just pull out of my dick either, they blew. My unstretched cock burst without touching, sending the sperm fly. It arched through the air landing on my shoulder, grazing my cheek and getting into my hair. A brackish white splash hit the couch next to my head where it soaked in fabric. With the deep intensity of my orgasm, I didn’t realize the effects of those first incredible shots until my consciousness came back. Then with surprise, I realized the source of the wet sensations on my skin.
I could have cumunduly fast on occasion, but I had never cum before without at least some contact with my cock. The orgasm didn’t seem to stop and I could feel the oozing of 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.
Wow, that’s a lot of Mike, she says running her hands through my cream.
I reached out to touch my dick. I wanted to milk everything that was left of the sperm and the feeling I could. Taking my still hard tree in my hand, I slowly stroked myself, while Sheri massaged my sperm into my stomach and chest. I felt so good until I tried to feel my. I was shocked to find that they were gone.
Stunned by the damage I had done to myself, I reached out with my other hand to confirm. With panic in my voice, I asked Sheri, What happened to my?
It was only when I stood that my nuts came back slowly. With my orgasm, they had contracted completely inside me. I had never experienced anything like it. I wish I had, because instead of panicking about the damage I thought did for me if the manipulations, I could instead just appreciate the resulting sensations.
Once the crisis was over and most of the laughter at my expense had passed, Sheri and I returned to our delight. Not only were we able to make sure I didn’t have a lasting disability, but Sheri was also much more accommodating when I paid her back in kind.
What’s Good for the Goose and Goosing the Gander (The Handjob Series)