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 brake 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 be home, a certain amount of subterfuge was required. As luck would have it the balcony off my room, also led to a widow 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 was 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 over-sized 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.
Sherri 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 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 quite 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.
