My name is Jay and though I may not be the biggest stud there ever was, I still manage to get myself into enough interesting situations that it keeps me pretty happy with my sex life. I seem to have an unusual sense of timing when it comes to sex and trouble. Now I'll be truthful, I'm not movie star good looking but I'm not homely either, I manage to get my share. I'm six feet tall, about two hundred and fifteen pounds, with dark hair and dark eyes, dark skin. I've never considered myself cute, more of the gentle bear type. This is just as well because the women I am attracted to seem to like that kind of man, strong and kind, handsome but not a pretty boy. My preference in women is all over the map. I like 'em big, small, man I like 'em all. This lack of fussiness has helped me meet many ladies and make them friends. One of these friends is Ann.
Now Ann has recently returned from Guatemala, she is something of a mercenary teacher, a rambling rose, you know, has syllabus will travel. She is actually my sister-in-law, or rather a step sister-in-law. She and my wife are step sister's but they act more like Siamese twins most of the time. They're both nuts but are a real blast to have around. For being step sisters they look amazingly a lot alike. They're both about the same height, around five and a half feet tall with dark hair and dark eyes. They're both slim, but athletically slim, with near perfect breasts, about a handful. Mary, my wife, has nice, pink, loonie sized nipples. Now knowing how these two feel about each other I haven't really considered the possibility of getting with Ann and perhaps ruining their relationship, but I've definitely fantasized about seeing that body covered in sweat, sliding in ecstasy under me. I'm only a man, a very imaginative man and though I've had several fantasies come true, some things are just not worth fucking with.
Well Ann has been in town studying massage therapy, and since I play Varsity Rugby for our University, I've been getting quite a few free massages so she can practice on someone with a little muscle mass, most of the students in her class are female. So every Friday I get an hour long massage for free and for the most part it hasn't been weird, with me sporting major wood or anything, it's been pretty platonic, well as platonic as I could manage anyway. Sometimes it takes a concerted effort not to really present a tent in my pants when I roll over after she's done with my back. While I receive my massages she is usually studying from the board in her class room. I work out so I'm fairly familiar with my muscle groups and names so I help her with their pronunciation and how they feel to different techniques. It's been a beneficial arrangement for both of us so far.
Well, Ann has to give these massages at her school because that's where the massage tables are. Some of her friends however have tables of their own which fold up for easy transport. I offered to make one for her at no charge to show my appreciation for her gentle therapy. It only took a couple of weekends to build and while she waited she cleared out a room at her place to set up her shop. It had cut flowers, a small waterfall, like the ones you can buy at the drug store, it had incense, scented oils, and soft music. This place could really put you to sleep or at least on a different astral plane. Well it was a Monday when this table was done and Ann didn't have any classes because of a plumbing problem at her school so I called her and arranged to drop her table off that afternoon. The table fit nicely into the trunk of my car and I picked up a couple of coffees from Tim's on the way over.
Ann was rearranging her stuff in this newly appointed room when I showed up. She was comfortably dressed in a loose T-shirt, some green hospital scrubs and a pair of birkenstocks, she wore a blue bandanna with a beer logo, like a head band. I carried the table in and showed her how to set it up and put it away, then we took a break and finished our coffees. Once again she offered to pay me for the table but I told her it was a family discount and besides I would rather keep getting massages. With that she tossed her cup in the trash and grabbed my hand and led me into her new room, she was going to give me the honour of being her first client.
I pulled off my shirt and moved to lay down on the table but she stopped me. Since she was a student I only received the massages she had learned in class and she hadn't studied the legs yet. Well as I was about to lay down she told me she was going to give me the works since she'd studied the lower body the previous week and needed to practice on someone. I said fine and she told me to strip down to my boxers and put a towel around myself and get on the table, then she left the room while I got ready. I stripped down, got on the table and covered myself with a sheet then called her to let her know that I was ready. She returned and taped up some of her notes on the wall in front of us.
I had never really felt nervous about our sessions, aside from the first time but then again she had only ever massaged my back, neck, shoulders and face. I didn't think this would be any different. With the music, the small waterfall, the smell and her soft but firm hands forcing the tension from my back I was almost ready to fall asleep, then she pulled the sheet up and exposed my legs so that only my butt was covered with the sheet. Still I wasn't all that concerned until she started to massage my feet. This perked me up. For some reason this felt different. Her hands were so soft but so strong as they worked on my calves. She spent a lot of time working deeply into the muscle. When she moved up to my thighs and started to knead my hamstrings area I felt a stirring that up until now I had managed to suppress. Her hands massaged my thighs and every so often she would work close to my butt with her fingers working my adductors and abductors, the outside and inside of my thighs. The music played the water burbled, Ann was breathing heavily from her exertions, and I was fighting with a world class Woody. She mentioned that I seemed a bit tense, so I tried to relax, that's when I lost the battle with the bulge.
Her tranquility tape switched sides and she told me to roll over. I was hesitant but turned over figuring it would be worse if I didn't. The sheet was tented from my erection but I kept my eyes closed and tried to pretend that I was oblivious to my condition. Ann was silent for a moment but then she went to work on my shoulders and chest. The boner wouldn't go away and only seemed to get harder the more I tried to will it away. Ann moved down to my feet and started with my chins trying to inform me about shin splints and their causes. When she moved up to my thighs I held my breath but she went to work like a true professional, I fought to keep myself under control when she worked close to the top of my quadriceps, only inches from my aching hard-on. Ann tried to ease the situation by repeating all the muscles and tendons in the thigh and the injuries that she learned about and how to treat them, I might have been able to will my erection away at that time if she hadn't turned to reach for the bottle of oil and smacked my cock with the back of her hand. We both froze for what seemed like an eternity then we both cracked up laughing. We laughed so hard we couldn't hardly breathe. My boner eased up a bit and we felt some relief from the tense massage.
She said that she knew that she would have to face that situation sooner or later and she had been dreading it, not knowing what she would do when the time came. She said she was glad her first time was with me or she might have been too grossed out by a total strangers cock. Her use of the word cock gave me a start but I never let on that I was surprised. Ann was a bit giddy as we talked, her on a stool and me still on the table. As she rambled on in the conversation she let it slip that Mary had mentioned the size of my dick but it had still taken her by surprise. This last bit had slipped out and we both paused for a second both noting that we were in strange territory, both feeling that there was a strange energy in the room.