My early years, sexually, started slow but ramped up quickly. Maybe I was making up for lost time, who knows. I didn't date at all in high school, I was more of a Dungeons and Dragons player than a player. In college I dated a little and then ended up in a long term relationship which lasted almost two years, two very lean years. In my last year of college I was alone and fairly well worked up, but mostly clueless about what direction to go in.
At that time I had a friend, Dena, which I spent a lot of time hanging out with. I was hot for her and she seemed indifferent for me, but we were good friends. We spent a lot of time together and I was often over at her dorm, which consisted of half a dozen single rooms around one common area. We would hang out, make meals, sometimes her roommates were around, sometimes it was just us.
During that period of my life I had studied massage and I had a vast collection of scented massage oils that I used to share with my friends. They would go through them one by one and then I would mix up a special scent just for them, should they want a massage.
I offered Dena many times but she declined. One of her roommates, Cindy, took me up on the offer once. Cindy was very friendly and attractive. I always thought she didn't care for me much as she didn't talk a lot, especially to me, so it was a surprise when she accepted.
After finding just the right scent for Cindy we retired to her room and I got things set up. We didn't have a table, so we used her bed, which was firm enough but not ideal. I explained to her that the main goal was to have her relax and enjoy and to that end she should be comfortable and stay warm. It was up to her as to what she would wear and how we would proceed. She understood and while I was out of the room she stripped down to her panties and bra and laid on the bed with a sheet over her. I proceeded to give her the best back and leg rub I had learned to do all while staying as detached as I could as she was even more attractive with what little she was wearing. After about an hour I wrapped things up and gathered my stuff and Cindy just melted into a puddle and went to sleep while I left.
Later that week I was back at the dorm and Cindy asked about the massage. She asked if it was a one time thing, to which I said it wasn't and I'd be happy to do it again. And so I did, maybe once a week for a month or so, each time getting more comfortable with relaxing Cindy. After the sixth or seventh time I was working on Cindy's leg and when my hand slid up the inside of her thigh Cindy let out a little noise. I hadn't been paying attention too well so I simply moved away and apologized thinking I had hit a sore muscle. To my surprise Cindy answered that it wasn't a problem and that it felt good.
To this my mind started to race, I figured I knew what she meant and that just excited me some. I slid my hand back up her leg and worked the muscle a little more, moving closer to her panties. She sighed again, almost acknowledging I should continue, and I did. I gently worked around and as I did Cindy responded by moving her hips and pushing back against my hand. As my hand began grazing her panties I could feel her breathing quicken and she made more and more pleasing noises. Then suddenly she clamped her legs around my hand and shuddered.
The only thing she said was one whispered, "Yes."
After a few seconds she rolled up onto her side and snuggled in to go to sleep, same as she had every other time. I had no idea what to do, this was my first 'happy ending.' I packed up my stuff and left as I had in the past.
Later that week I was back at the dorm and Cindy was there as well. After a while it was obvious that she was in the mood for another massage and I was more than willing to provide one. I had been wondering what would happen, and now I was about to find out.
Cindy was very warm and personable that evening, everything started out normal and finished the same as it had last time with Cindy riding against my hand until she orgasmed.
I guessed that this would become our regular massage, and I was right, but the next time it got even hotter. This time while I was in mid massage Cindy just up and rolled over. Up to this point I had only massaged Cindy from the back, but now here I was with her smiling up at me, pretty pink panties and all. I stopped for a few seconds and then just started up massaging again. As I neared her panties Cindy acknowledged by simply saying, "Mmm hmmm."
This time I worked all around her legs and up into her mound. Cindy rocked against my movements panting and moaning with the occasional hum or encouragement of a whispered, "Yes." I started to push against her pussy through her panties and she quietly begged, "Yes, yes, please." She came hard against my fingers as I worked her slit through the cotton material, shuddering over and over. When she was done she said, "Very nice," and then rolled onto her side for sleep. And I left.
At this point I knew I was no longer just a masseur with a little happy ending, I was entering into whole new sexual grounds.
I was really turned on by all this and regularly took matters into my own hands afterwards, often with Cindy's scent on me. I think I was enjoying it as much as her, maybe.
The next time I saw Cindy for a massage she had erased any question about her intentions the moment I started. When I moved the sheet back I found she was not only already laying on her back, she was also completely naked. My eyes moved down her perfect body from the turf of blonde pubic hair up to her perfect perky breasts and then ended meeting her eyes. I thought for a moment she might blush but she just smiled back at me. I started but had only been rubbing for a few minutes when Cindy reached out and drew my hand down to her pussy. Once my hand was on her lips she relaxed back down and let me rub her. She rocked back and forth in rhythm with my strokes and my fingers found her slit. I gently grazed her lips but she kept thrusting forward for more so I obliged. One moment my fingers found her clit and she jumped with a yelp, then settled in with more moaning. That night she came hard as I fingered her pussy, by the time she rolled over I was hard as a rock and hoping she hadn't noticed.
I pleasured Cindy many times like this, each time bringing her to orgasm and then her going to sleep. At maybe our dozenth session, Cindy watched me as I gathered my things, instead of rolling off to sleep. She looked like something was wrong.
When I said good night she asked me to wait a second. I did, and then I asked if everything was all right.
She sat up in the bed and drew the sheet around her like a robe. "I noticed that recently you've been kind of excited about this," she said, motioning to my pants. My cock had shrunk some but was still bulging in my pants. I wasn't sure what to say. Cindy just looked at me for a bit then asked, "Does this turn you on?"
I said it did, and that she is incredibly attractive.
Cindy didn't seem to know what to do with what I was saying. She started and stopped saying things a few times then said, "I guess we have gotten a little out of hand."
"No, it's all right," I responded.
"I bet it is," she replied. "So, I don't understand. This is all getting you hot? Is that why you are doing this, to get off?"
"No, not at all, things just changed and I didn't know what to do, I didn't want to upset you, and I liked, well, pleasing you."
Cindy still looked confused. "But you like touching me, I mean like, like touching me, and seeing me naked?"
"Yes."
"Do you imagine fucking me?"
I wasn't sure what to say, she seemed to be getting mad. "Umm..." was all I could manage.
"Am I some kind of fuck fantasy or what?" Her tone was getting more stern.
"No, it's not like that, I like you, I mean I wouldn't do anything."
"So, do you jerk off, thinking about me?" Her tone slid down a couple notches, almost playful.
"Sometimes," I replied.
"Well I don't think that's right."
"I'm sorry..." I started, but she cut me off.
"If you're going to be jerking off to me I should get to see it, you've seen me get off a lot, it's only fair."
I wasn't sure what to do, I just stood there in the middle of the room.
"Come on, I want to see it," she said pointing at my pants.
I was only half hard now and all confused, was she asking me to take my clothes off?
"Come on, strip, I want to see yours, you've seen mine. Let's go."
I froze for a few seconds uncertainly and Cindy motioned around with her hand pointing at me as if to say hurry up so I began to unbutton my pants. Cindy smiled and I continued. I slid my pants off, my cock started growing. Then I slid my shorts off and my cock sprang out.
"All of it, completely naked mister." She motioned again with her finger.
I complied and stripped it all off. There I was buck naked in front of this amazingly hot woman with a throbbing erection. I didn't know what was going to happen next.
