True story about my mom's college friend. No intense sex or anything, but the experience had been the fodder for many of my masturbation sessions since.
The recent stories about women in their underwear on Solo are great, and remind me of an experience I had when I was 14. My mom and dad got divorced when I was 11. I lived with my mom, and during that summer she had an old college friend visit her from out of town. She stayed with us for two weeks. At the time I guess my mom was in her early 50s and I suppose her friend was probably about the same age.
I had begun masturbating regularly the summer before and was perpetually horny like all guys my age. I had seen a few of my friends' dirty magazines before (mostly Playboy and Penthouse) but had never seen a girl or woman naked for real, or even in their underwear - although I thought about it ALL the time (the only exception was once seeing my mom with her blouse unbuttoned one night before bed, but that was definitely NOT a turn-on!).
My mom's friends name was Helen, and at first there was nothing about her that made me think of her in a sexual way. She was heavyset (probably 180 lbs), with short, graying mousy hair and large saggy breasts. She wore pantsuits or large, flowery dresses that she used to disguise her weight the best she could. The one thing I did like about her was that she was a very outgoing, 'fun' lady; she laughed a lot, said what was on her mind, and seemed very at ease with me (she had no children of her own, and was also divorced). After the first few days I felt like I had known her for years. She was a great cook and made us some unbelievable dinners, and each of the first few nights she stayed up late with me watching TV until the early morning hours, long after my mom went to bed.
On one of these nights, at about 12:30, she told me she was tired and was going to go to bed. I wanted to watch the end of a movie we had on, and told her so. I settled back on the couch and about 10 minutes later I saw the hallway light flick on (the section of the couch I was on faced the first floor hallway where my mom's bedroom and the guest bedroom was - mine was upstairs), and then Helen was walking down the hallway towards the living room. I immediately noticed that she was wearing a bathrobe that was COMPLETELY open and underneath she had on only her bra and panties. My eyes practically bugged out of my head, and at first I thought she was on her way into the bathroom (which was also in the hallway).
When she walked past the bathroom door and into the living room I didn't know what to do or where to look. I shyly looked towards the TV, but at the same time I wanted to stare right at her. As she casually walked past me into the kitchen, she said she just wanted to grab a glass of ice water before she went to sleep. I vividly remember actually trembling, and my penis also had begun to get hard. I heard her getting ice and filling her glass, and then she stepped into the room and stopped and asked me if I would like anything to drink. I turned and looked at her and she was smiling, and I couldn't help myself as my eyes traveled from her legs up to her breasts and then finally to her face. While it didn't take more than two seconds, I guess it was pretty obvious I was checking her out. I told her no and she smiled at me, making no attempt to close her robe. She gave me a quiet 'good night' and was gone.
I waited about five minutes (I could not have cared less about the movie at that point), the whole time fidgeting with my hard-on through my shorts. Then I clicked off the TV and practically ran upstairs to my room where I proceeded to strip naked in no time flat, jump under my covers and begin to frantically masturbate. It took me no more than two minutes to come, and it was very intense as I pictured Helen in her underwear standing in our living room. Keep in mind that she was no Miss America, and her rather large midsection was partially covered by her panties (actually it was a girdle), but to me just seeing her in her underwear and her huge breasts in a lacy bra was incredibly erotic.
The last night she stayed with us we went out to a restaurant and had a fantastic meal. Afterwards we all returned home tired, especially my mom and Helen. My mom went to bed immediately, and Helen and I sat on the couch watching the news for a while before she very explicitly told me she was going to change for bed. As she did so she made a point to smile at me, and I had no idea why. It just seemed kind of weird to me how she told me so clearly that she was 'going to get ready for bed' and her devious kind of smile. I arranged myself on the corner of the couch facing the hall on the outside chance she would move between the guest room and bathroom in her underwear. Much to my surprise-and delight-a few minutes later I heard the squeak of the guestroom door and heard Helen coming down the hall. She was clad in only her panties: no robe and no bra!
She paused momentarily in front of the bathroom and glanced into the living room and smiled, then slowly went into the bathroom and shut the door. I began shaking again, and my breathing got heavy, and of course I got an instant erection. Her breasts were like large balloons that sagged half-way down to her belly and were capped by enormous brown nipples. It was obvious that she had wanted me to see her, but I was nervous and afraid. I wasn't sure what would happen next, and was terrified my mom would wake up and see her friend half dressed in the hallway, looking at her son.
In less than a minute the door opened again and she stepped out, this time completely naked! She didn't look my way but VERY slowly began to walk down the hallway, and I got a very clear view of her large, naked ass, the first naked woman's ass I had ever seen. The image was burned in my mind, and I thought that was all I would see, until she turned and took a few steps back towards the living room (she was about 20 feet away from me at that point) and stood with one hand on her hip, and with the other she blew me a kiss and said in a loud whisper, 'Hope you have a nice sleep!'
I saw her full frontal, large belly and all. But I also saw a very thick, wide expanse of pubic hair between her legs, and soaked in her tits and humongous nipples. She stood there for another several (five maybe) seconds, practically posing and smiling that devious smile, before she walked down the hallway, went into the guest bedroom and closed the door.
I of course bolted almost immediately up to my room and had another intense masturbation session, and woke up at 3 am and jerked off again thinking about what it would be like to actually touch Helen's tits and her hairy vagina and screw her from behind and ejaculate on her ass.
The next morning we were all up early as Helen had to get on the road to drive back home. As I helped her bring her things to her car, she kept thanking me and telling me what a good boy I was, and when I got my final goodbye hug she held me a bit tight and I felt her grind her crotch against my hip for a second. That of course got me horny, but before I got hard she gave me a long kiss on the cheek and stepped away. I was standing by the driver's door as she got in the car and my mom was on the curb, so as Helen swung her legs into the car she let her long skirt purposely rise up high and she opened her legs, allowing me a clear view of the crotch of her panties. She smiled at me and winked, and a minute later she was gone.
It's obvious to me now 20 years later that this lady was probably very horny and didn't get a lot of attention, and she got off on exposing herself. I had no problem with it, and those nights I just described were (and sometimes still are) the center of some of my best masturbation fantasies.