I confess...I have a fetish for older women that has only gotten stronger as the years have passed. The reason for this is the best (actually the ONLY *really* good) sex story I have.
This was 8 years ago, the summer of 2005. I was 15 and it was the July 4th holiday. My parents had a little pool/barbecue party for the block. I was swimming for a little while. When the sun started to go down I decided that was enough so I went upstairs to change. I dried off and got into a pair of my gym shorts, just for the time being so I could hang my suit in the bathroom and get a shirt and some sandals.
I went to the bathroom and was waiting. I thought- weird, the only people I figured would be using the upstairs bathroom was my mom or dad or sisters but they were all outside. The door opened after a minute. It was Mrs. Batelli, who was my mom's friend from the block. When she came out, she was adjusting the top of her sundress- really nice dress, orange with a pretty good cut, and I'm sure you know exactly where my eyes went. She was probably about 41-44 and she was nicely proportioned, probably around 145 and 5'6" or 5'7". Shoulder length auburn hair. Had a good tan on by that point in the summer. Her name was kind of deceptive, she wasn't Italian at all, that was her husband's name. I think she was some kind of European little-bit-of-everything mutt, but the tan was pretty far from her natural skin color. And it looked good. She had the legs out, nice shape- not very long but hey. Her tits were very nice, very perky for her age. Not huge, probably a small C or large B. I was staring dead at those suckers because in adjusting herself she was really moving them around and hadn't noticed me. In fact, I think she was about 6 inches away from bumping into me before she realized I was there.
She just went "Ooh!" and stepped back, definitely startled.
I just stood there, probably with some idiotic look on my face because I just got to watch a solid 6 seconds of tits bouncing around.
I expected her to react adversely, but she put her hand on her chest and started laughing- actually quite hard, much harder than the situation probably warranted.
She was like "Shit!" and kept laughing. I had no clue what to say, just kept smiling like an ass.
So she takes two steps, stumbles right into me and gives me this big half hug with one arm so that those firm tits and pressed right into me and she goes "You scared the HELL out of me!" and just kept laughing. I had still not said anything!
This is when it dawned on me- how long she'd been here, since noon, I wasn't keeping track of her drinking but she was fairly petite- this lady was HAMMERED.
So I think I said something like "Glad to see to you too,"
She said, "You didn't talk to me all day!"
We exchanged bullshit for about two minutes, none of it is interesting. Finally she said, "Your house is nice. I'm staying here. I'm going to sleep over."
I was kind of chuckling at this point and I just wanted to humor her so I said "Cool!"
She goes "Let's have a sleepover party" and I answer "Sure, that sounds like fun."
And then out of nowhere, she goes "Do you trust me?" all serious all of a sudden and I answer "Of course," because I think she's going to tell me something weird or something.
But no, as soon as I say it, she comes right up, pulls me in and gives me this deep, fucking awesome tongue kiss. Let me tell you. I had NO clue what was happening. She was working her tongue all over my mouth and I got instantly hard. She tasted like spearmint and- I didn't know at the time, but now, unmistakably- rum. And lots of it. Captain Morgan and Doublemint. I'll never forget it.
After about twenty seconds, she pulls back and goes "Somebody's gonna see this" and I think "FUCK! Come on!" but I was very happily mistaken because she grabbed my hand and pulled me into the bathroom.
I threw my towel and suit into the tub. She locked the door and put on the lights and the fan (cover up noise? I dunno) and she pulls me into the sink, falling, so that we both hip-check the counter. More tongue kissing. Fucking awesome, none of that awkward high school bullshit.
Her tits were right up on me and after a minute I started feeling bold so I slowly raised my hand up the back her leg and felt on her thigh. She had damn good skin for a middle aged woman, must have lotioned up all the time. I was wary, and frankly, a little worried that a wrong move on my part would blow the whole thing and I'd kick myself forever. But I was also horny as fuck at this point and just wanted to touch all her bits. But, to my delight, as I felt on her thigh she pulled my hand and guided it right up the dress onto her nice, firm ass. She was wearing the high-cut bikini panties. Guess she hadn't embraced the thong yet. I didn't care. It wasn't a big ass, but the texture was fantastic. Firm, but soft. Not muscular but not flabby. I was throbbing at this point.
She must have known, because she grinding the top of her leg against my shorts. She had me salivating. I pulled my other hand up her dress and onto the other ass cheek. Fantastic.
Then she reached down and fondled me through my shorts and gave me a little squeal. It was a lovely little sound. She stopped to spin me so I was up against the counter then back away and pulled her dress over her head (with surprising grace) to show off her body. She had a nice figure, cut pretty well for her years. Her bra was white and strapless. She whipped it right off. I got my third really good look at some live tits. This was the epitome of awesome. I felt like a fucking champ. But it was only the beginning.
She sauntered over to me and smiled and said "Show me" in the hottest voice I'd ever heard. I immediately dropped my shorts. I'm not going to brag about my cock. I'm no mandingo, but I was hard as a motherfucker. She said "Nice" and dropped her panties.
Her pussy was beautiful, symmetrical. None of the curtains you might expect on an older mother of two. She was shaved smooth. I'm pretty sure I audibly said "Fuck"- as in "Fuck, I am going to wake up any second now."
She came up to me and put her lips back to mine, and as she did she cradled my balls and started carefully to appraise my cock. She was teasing me. My heart was beating like it was going to explode. Then she got up on her toes and slid her pussy over the top of my shaft. It was like heaven. I don't know how I didn't cum right then and there. She leans into me and I think she asked "Do you want to help me cum?" and I just nodded "Yes" even though I didn't hear her completely. Whatever, she could have asked me to to stand on my head.
So she grabs my head and moves me so I'm about eye level with her tits and pulls me into them and says "Kiss my nipple like I kissed you". I tried my ass off to be good. Who knows if I was. Soon, she was purring like a kitten. She dipped her hand down into her snatch and started playing with her clit. I could hear how wet she was. I told myself "Shit, good, I'm doing it right."
She took my hand and guided it to her pussy. Her slit was so wet. She used just my fingers at first, but soon she was using my whole palm- long strokes, she had me cup it hard and my whole palm was getting slick.
Then she asked, "Do you have a condom?"
- FUCK -
I mean of course I didn't. I wasn't sexually active. My heart sank. I was abut to lose my virginity and I didn't have a fucking rubber.
I said, "No". She said, "It's okay."
My cock was denied entrance, but she balled up my hand and slid my index and middle fingers inside her and fucked away, vigorously. I went back to licking her nipples, harder and faster with the rhythm of her body. She came, I felt her snatch tighten as she squeezed and she threw her head back.
It was something to behold, indeed, but fuck man, did I regret not having a condom.
"Thank you," she said, with kind of a giggle.
"Now-" she said, and dropped down to her knees. I put my palms flat against the counter. She pulled my hips forward, grabbed my butt a little, and then slid her lips over my cock. I'm a little biased, but it's still the best head I ever got. Her skilled tongue lapped over my head and shaft and she gently caressed my balls. It was like waves of electric everytime she bobbed. She took the whole thing. I only lasted two minutes, having been dying for release for so long by this point. I came buckets and she moved down even deeper as I did so that it ran down her throat. She swallowed every last drop and cleaned me off with her tongue as she pulled back.
The whole encounter lasted less than twenty minutes. After I came, she started to dress herself again and said "Don't tell anybody, ok?" I nodded, lightheaded.
She left, and I laid in my bed for a few minutes to recuperate. When I went back downstairs, she was gone. Her husband was too, so I guess he decided they'd had enough and they were going home. I have a lot of theories- the husband was some kind of professional, like a lawyer or something. I first thought she was neglected but later I found out that he was most likely cheating on her. I never found out, but what does it matter?
Naturally, I kicked myself for not having a condom. It was about nine months later when I finally lost my V-Card.
After the encounter, I saw her less. I always wanted to try to see if she would ever be alone so I could ask her about it, but the opportunity never presented itself. Later, I thought about maybe trying to blackmail her, but I had a pang of consciousness and thought it would be shitty of me to do that to the lady who gave me my first great sexual experience out of the blue with no strings. I still have mixed feelings. I wish I would have hit it.
Eventually, she divorced the husband and moved away, out of the state and remarried. I haven't talked to her.
I took a few things away from this- first and foremost ALWAYS HAVE A RUBBER. you never know when your mom's friend will suddenly and for no reason decide to get frisky with you. Secondly, I still love the older ladies. I've only had a couple of other experiences after, but the first one was the best and most special. I still frequently knock one out thinking about that blowjob and fantasizing about what could have been.
Oh well, the inexperience of youth, etc.
That's it. This story is 100% true and I hoped you enjoyed it.
