I know that what I'm about to tell you, to most people, is considered as not normal and strongly considered taboo; I understand that. However, sometimes things happen and people find themselves in situations that are unique and more than a little bit unusual – emotions, desires, and deep needs often cause boundaries, sexual boundaries that is, to get stretched. It happened to me and I can tell you that it was unexpected and, at the same time, very pleasant.
I was in my junior year at college and I decided I needed some time off during the summer break. I didn't particularly want to go home to San Francisco. My parents were planning to be vacationing in Europe so I accepted an invitation from my aunt Sandra to come and stay with her until I had to return to school. She lives alone in a large house on a hillside above Hollywood, California and has a great view of the city and most of southern California. Ok, I admit it; another big reason for my decision was that Hollywood is a great party town if you know the right places to go.
At the time Sandra was just a little over a year divorced from her second husband and obviously I knew that she would be glad to have the company. She's my mother's sister and even though there's always been some tension between them, she's always been my favorite aunt. I can't explain it but, for some reason, she and I have always been very close. I enjoy being with her so I was really looking forward to staying with her.
Sandra's in her late fifties and she's still a very attractive woman. In some ways I think she's actually gotten more attractive as she's matured. She's active and has always taken very good care of herself; she dresses well and has always had the face and body of a much younger woman. As I got older I came to realize that there always seemed to be a very slight – almost undetectable air of erotic tension about her. Perhaps it was in the way that she moved or it was her natural self confidence, but I've always sensed it whenever I was around her.
There were occasional family rumors about her and her first husband but it never mattered to me. I've always assumed that, as attractive and sexual as she is, she must have been a very sexually active woman – not only with her husbands, but also with several men (boyfriends) that she'd secretly had during and between her three marriages. She never openly said anything about it but it was something that I felt couldn't be hidden very well within the family.
About a month before the semester break my girlfriend Brianna and I broke up and it had been a little tough on me. I was young and, as usual, always horny and slightly restless – probably because I hadn't had any sex since the breakup. However, like any normal 24 year old male if I couldn't have sex, I masturbated almost every night before going to sleep.
One night I'd been out partying at one of the clubs and I didn't get home until a little after midnight. The house was dark and I went straight to my room and got undressed. It was a warm evening and I lay down on my bed; the cool sheets felt good against my naked body. I was thinking about one of the girls I'd met at the bar earlier in the evening – I'd forgotten her name (maybe she hadn't given it) but she was very pretty and had an unbelievable body and I couldn't help but wonder what she'd look like naked. I lay in bed and began fondling my cock which was about half-hard. I was tired and I wasn't sure if I would jack-off or not but, naturally, I enjoyed the feeling of my own fingers as they probed my scrotum and shaft. I closed my eyes and pretended that the girl from the bar was caressing my cock and, in moments, my cock was hard and throbbing and I slowly stroked it. I also thought about my last girlfriend from college, Brianna. She was very good at jacking me off; actually, she was much better at it than I was. She knew exactly when, and where to use her fingers, tongue, lips and fingernails on my cock that would produce a very intense orgasm in me. Often I was surprised at the large amount of cum that she managed to drain out of me when she jacked me off.
As my hand stroked steadily up and down my hard shaft a few of my most lurid fantasies flashed through my mind adding to the pleasure I felt. Women that I knew...women that I'd never actually met but perhaps, briefly, saw somewhere, came to me...usually naked, and of course desirous of sex, my cock, and of my attention.
The steady rhythm felt good and I could feel the enjoyable tightness in my groin beginning to build signaling an impending orgasm. The muscles in my lower belly and thighs began tightening and relaxing with the rhythm of my hand as I worked on my own cock. My one deepest fantasies was actually little more than small fragments of erotic thoughts suddenly surfaced through the static that was in my mind at that moment – Sandra, in all her beauty, was lying on a black velvet bed smiling at me as she motioned for me to come and make love too her. I was a little uncomfortable and I quickly replaced the thought with one of Brianna sucking my cock. The urgency was building in me and I was only moments from coming when I opened my eyes and in the dim light of my room I could see Sandra standing just inside the bedroom door watching me. I immediately stopped jacking off and tried to pull the covers over me.
She held her robe closed at the neck and when she realized that I saw her she stammered an apology – something about making sure I got home alright or if I was asleep yet. She turned and quickly left the room. I was so surprised, I just lay in bed not sure what to do. I didn't know how long she'd been watching me and I was a little embarrassed to say the least, however, I felt oddly aroused at being caught, especially by her.
I stayed in bed for a while thinking about what had happened before I got up and went into the bathroom and splashed some cool water on my face. As I looked at my reflection in the mirror I thought it would be best if I went to her bedroom and tried to explain myself or, at least, apologize for not closing the door to my bedroom. I pulled on my boxer shorts and walked down the dark hallway to her room. Her door was partially closed and her room was dark and I wasn't sure if she was asleep or not. I remember lifting my hand to knock softly when I heard a soft buzzing sound coming from her room and it made me freeze. It took me only moments to realize that the sound was that of a vibrator. The sound continued and I could just make out the sound of deep breathing and an even softer whimpering. I thought about turning and going back to my room, yet, I simply stood there listening. I gently pushed the door open and even though her lights were turned off there was enough soft ambient light for me to see that she was lying on her bed completely naked. Her legs were spread and both of her hands were between her legs. As I suspected, the buzzing sound was coming from a long white vibrator that she was using to gently caress her clitoris and labia. My cock began stirring and with each deep throb it became harder and more erect until it was fighting against the material of my shorts to be standing straight out from my belly. I really didn't know what to do at that moment. I knew it would be best to go back to my room but I didn't want to move as I watched her. Her breathing became stronger and her actions more definite until I saw her body begin to tighten. Suddenly, she drew her legs up against her chest as she let out a low, breathy, strained moan indicating that her orgasm was flooding over her. My hand was on my cock stroking it gently and, as I was about to turn and go quietly back to my room to finish jacking off, I heard her soft voice call my name and ask me to come in to her room – I was stunned that she knew I was there watching her.
