Exhausted, we soon retired to our respective sleeping areas. Victoria wiped herself off but neither of us bothered to put any clothes back on. We just crawled under the sheets of her bed and were soon sound asleep.
When I woke up the next morning, the room was filled with natural light from a skylight above. I got up to use the bathroom and brush my teeth (I’d learned to always pack a toothbrush in Japan; you never knew where you’d end up) and then Victoria did the same. When she came back, still totally naked, she crawled back into bed. Then she told me to roll over onto my stomach because she wanted to give me a massage.
I obliged and a moment later she climbed on top of me, straddling me around the waist, and began working my shoulders with her hands. It was very relaxing. After a while, she stopped and I heard a squishing sound. I craned my neck and saw that she was squirting massage oil onto her hands. She must have brought it with her when she came back from the bathroom. A moment later, she was applying the oil generously to my back and shoulders. It was warm and the feeling of her hands gliding across my skin was very sensual and arousing. I could feel a little movement in my cock.
She continued to massage my back and neck for a least five solid minutes. Then she stopped again and I heard the sound of more oil being squirted from the bottle. I felt more of it land on my back and when I craned my neck again, I saw Victoria squirting some of it onto her own chest, where it dripped down between her breasts, some of it landing on my ass. She then used her hands to spread it across her breasts and stomach. That was quite a sight to behold. Her skin was glistening in the sunlight. A few seconds later, she leaned down until her breasts were touching my back. Then she began sliding up and down on my back, massaging me with her breasts and body, kissing my neck. I was instantly rock hard.
After a few minutes of this, she got up on her knees and told me to turn over. When I did, I could see she had the bottle back in her hands, she squirted a few generous dollops onto my chest and began spreading it around. Then she squirted some onto my stomach, put the bottle down, and began spreading it down onto my cock and balls. Once we were both covered more or less entirely in the oil, she leaned down and began kissing me. She then began gliding up and down on me, using her breasts to massage my chest. My well-lubricated cock slid up and down across her stomach, popping out from time to time from between her legs as she moved higher on my body. As she moved back down, my cock would sometimes get lifted off of my stomach and wedged between her legs, rubbing against her well-lubricated pussy and ass cheeks. It was an enormous tease. I wanted nothing more in the world than to reach down and thrust my cock inside of her, but I was content to let the situation play out, knowing I would get there eventually.
Sure enough, after a couple minutes of this slipping and sliding, physics took care of the problem. Without even meaning to, Victoria slid down at just the right angle and my cock was pointed in just the right direction, that it slid right inside of her. She let out a gasp of excitement when she felt what had happened and immediately shifted to a more vertical motion, moving her hips up and down as my cock plunged in and out of her pussy. It was fantastic. Wet and wild. As she sat up to ride my cock, I caressed her slippery breasts and slippery ass with my hands.
After a while, she wanted to try something different, so (very skillfully) she swiveled around to face away from me while keeping my cock inside of her. Then she leaned back so that her back was sliding up and down on my chest. As I continued thrusting into her, I used one hand to caress her slippery breasts and, with the other, I reached down between her legs and started stroking her clit. This was apparently exactly what she wanted because she immediately started moaning, loudly.
We continued in this position for a quite a while as she steadily built toward orgasm. Then, abruptly, she began rolling off of me to our left and reached out her arm to pull me with her. I turned with her and, without losing the connection, I soon found myself lying on my side, while she was on her back with her right leg up in the air, on top of mine. As I continued fucking her, she took over stroking her clit. We were now in a much better position to kiss and began doing so, passionately. With my left hand, which was now under my body, I reach underneath her until I was touching her well-oiled ass. I used my middle-finger to circle her anus, teasing it just a little. This elicited a positive reaction from her, so I went a little further, slowly sticking my finger in up to the first knuckle.
It was then that I got yet another surprise. Victoria stopped kissing me, looked me in the eyes, and said — in her quintessentially British way — “Jake, I want you to put your cock in my arse.” That was honestly the last thing I was expecting from this proper British girl and I was momentarily taken aback. I’d had anal sex a couple of times, but neither was a particularly fond memory. Both girls had done it merely to please me and had not been particularly into it. And in both cases, it had had been so pre-meditated, so non-spontaneous that it hadn’t felt very sexy at all. But this was very different. She was asking for it. And I could tell that it had taken her a lot of courage to do so.
I gently slid my cock out of her. It was still covered in oil as well as her own natural lubricant. I withdrew my finger and slowly positioned my cock next to her anus. Then, while I continued to kiss her, I slowly pushed in. She was incredibly tight, and, at first, I wasn’t sure it was going to work it all. But then the resistance gave way a little and the tip of my cock made its way in, about an inch or so deep. Victoria braced herself and squeezed my arm tightly. But she didn’t tell me to stop. Very slowly, millimeter by millimeter, I continued to push my way inside until I was nearly all the way in. It was an unbelievable feeling. So very tight. I began to thrust, ever so slowly, in and out. Victoria had now adjusted to the feeling and was clearly enjoying herself. She had resumed stroking her clit and her moans were becoming increasingly frantic.
She pleaded, “faster, Jake, fuck me in the arse.” I obliged, picking up my pace and knowing that I couldn’t take this much longer. Luckily I didn’t have to. After less than a minute, she came hard, almost violently, screaming “Oh fffuuucck, Jake!” The pressure on my cock caused by her spasming was more than I could endure. I too screamed “oh fuck, I’m coming” and let loose, shooting my cum deep into her ‘arse.’
As I pulled out and we each caught our breath, she had a huge, triumphant smile on her face. I said, “that was your first time. wasn’t it?”
She nodded and then leaned into me, grabbed my head with both of her hands, and planted a huge passionate kiss on my lips. She said, “you’re lovely,” which caused us both to laugh.
As we lay there recovering, I asked whether the last 24 hours had done anything to alleviate the regret she felt for having missed out on the whole single college girl experience. I told her that, if it makes her feel any better, I was single through most of college and never once had an experience that rivaled last night and this morning.
She smiled at that and then held up her hand, lifting a finger as she checked through each of her firsts from the last 24 hours: “Let’s see, first shag in the arse, check. First time watching other people shag, check. First time shagging in front of other people, check. First time getting shagged by two guys at the same time, check. First time shagging a monster-sized cock…”
With that last one, she abruptly stopped, clearly worried that she might have offended me with her reference to Ali’s cock size. I put her at ease, “don’t worry, we can’t all be Ali, I’m cool with that.”
She smiled again, “well, I’ll tell you one thing, if you were like Ali, I never would have let you get anywhere near my arse.” With that we both cracked up.
We talked for a while longer and I eventually got dressed, said goodbye to all three of them, and headed back to the train station.
I only ever saw Victoria one other time, a few months later. I was at an ex-pat bar in a nearby town, hanging out with some friends, when she entered with a guy. We made eye contact and she eventually came over to our table and introduced me to Paul, her fiance. We shared a knowing look, and I knew that she had not told him anything about our night together and did not plan to. I completely understood. The night we shared was amazing, but more importantly for her, I think it was what she needed to be able to move on to the next chapter of her life, without regret. That was the last time I ever saw her, but I think about her all the time.