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The homeless lady

General Sex Stories (Written By MEN)

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Old 04-19-2011, 12:00 PM   #1
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Smile The homeless lady

When I was 18 my bandmate's brother, who was at university in Manchester, had got us a gig there so we all went up there for the weekend. Our gig was on Friday, and the evening after we went out in the town. After I'd had a few drinks I left the bar to find a shop to buy cigarettes, but after walking for about ten minutes I still hadn't found anywhere that was open, so I began to head back to use the expensive cigarette machine in the bar. After walking for a while however, I realised I was completely lost. I didn't want to admit to being lost so instead of phoning someone I wandered around drunkenly getting even more lost.

After a while I saw an attractive homeless lady, probably in her thirties, sitting on a bench. I approached her and tried to explain what the bar I was in was like, because I didn't know the name of it. She laughed and offered to help me find it, and I asked her if she knew where I could get cigarettes, and she said she did so I followed her to an off-license where I bought a pack for myself and for her. We smoked and chatted together as we searched the streets for the bar my friends were at, and she was a really lovely woman, and I felt bad that she was sleeping rough. As we were talking she suddenly said to me "you know what you're really cute". I was a bit taken aback because I had never had a woman of her age show any interest in me before. I mumbled something like "thanks, I think you're really pretty" and then she looked me in the eye and said "do you want to have sex?"

"Erm, what?" I said nervously. She said she hadn't had sex with anyone for a long time and really wanted to with me, but that if I didn't want to it wasn't a problem. She was skinny but very attractive so I said "ok, where?" and she told me to follow her. As we were walking I told her I didn't have a condom on me, and she said "you don't need one honey, feels much better without." I stopped walking when she said this, thinking it was maybe a bad idea, but she said she was clean and couldn't get pregnant, but if I wanted we could go and get some condoms. Now you're probably thinking I'm an idiot, but I was young and stupid, and the thought of having unprotected sex for the first time was very exciting for me, so I said it was cool. I'd only slept with two girls up until then, and we always used condoms, but I was desperate to try it completely natural.

She led me to a building, I have no idea what it was but it had some toilets in it, and she went into the ladies and then put her head back round the door and told me to come in. We went into one of the cubicles and locked the door, and she immediately began kissing me very passionately, and I could tell she wasn't lying when she said she hadn't had sex for a long time. My cock was hard as a rock now and I grabbed her ass and pulled her body close to mine as we kissed. I pulled up her jumper and sucked her breasts. She wasn't wearing a bra but I guess she would have wore about a 28b, with delicious round nipples. I then unbuttoned her jeans and slid my hand into her knickers, which were already damp, and my cock got even harder when I felt a thick bush of soft pubic hair. I hadn't felt a hairy pussy since the very first time I fingered a girl, and I'd never put my cock inside one so to say I was excited would be an understatement.

I found her clit and began to rub it, and she began to moan as i slid my finger along her wet cunt. Feeling how wet she was getting, I couldn't wait any longer to get my tongue in her so I knelt on the floor and pulled down her jeans and knickers to her ankles. The sight of her thick dark bush, glistening with her juices, was almost too much for me, and then the smell hit me. Now I know a lot of guys will probably find it a turn-off, but I love the smell of pussy, the musky, feminine scent drives me crazy, the stronger the better. And this was strong! As soon as her knickers came down the cubicle was filled with the unmistakable scent of pussy, and I grabbed her ass and buried my tongue in her wet hairy cunt, licking up her delicious juices as she continued to produce even more on my tongue.

"Fuck me!" she moaned and I didn't need to be told twice. I tore down my jeans and rock-hard cock sprang out, feeling like it was going to explode with desire. I pushed my cock up to the entrance of her pussy, and I had to concentrate hard to stop myself from cumming as I felt her soft pubic hairs tickling the head of my cock. I had to push quite firmly to enter her because she was very tight, but she was also very wet so I slid in smoothly, and my god did it feel good. The warmth of her wet vagina gripping my bare cock was overwhelming, and I only managed a few thrusts into her before I started ejaculating into her. I grabbed her ass and thrust my cock as deep as it would go as I pumped my hot cum into her tight pussy. I held her and kissed her with my cock still deep inside her. "Wow, you really needed that!" she laughed and, a little embarrassed by my early finish, I explained that I had never had sex without a condom before, "it felt too good."

I was still inside her and still rock hard so she said "well I think you can manage to go again if you want to". I said I definitely wanted to, and she lifted her dripping pussy off my cock and knelt down to put it in her mouth. My cock was covered in a mixture of our juices and she sucked it deep in her mouth and it felt incredible. I could still smell her pussy and the feeling of her hot wet mouth sucking hard on my cock was making me want to fuck her again. "I want to fuck you" I said and she stood up and bent over so I could enter her sweet pussy from behind. It slid in easily this time, lubricated with my cum and her juices, and it was horny as hell to watch my bare cock sliding in and out of her juicy pussy, seeing her pussy lips sucking on to my cock as I pulled out of her. She had the prettiest little asshole I have ever seen, and as I was fucking her I contemplated asking if I could fuck her in her ass, but I never did, and it's something I still regret.

We fucked like this for a good ten minutes, and at one point someone came in to use the toilet so we had to freeze, my cock embedded in her cunt from behind, while we listened to a strange lady peeing into the toilet next to us. It blew my mind how good her vagina felt around my bare cock, and as soon as the lady left the toilet, we laughed and I fucked her as hard as I could until she was making way too much noise, and I shot my second load deep into her pussy. There's just something so emotionally satisfying about cumming inside a woman, so I'll never forget the first time with her.

I wanted to stay inside her all night, but it was getting late and I had to get back to my friends, so reluctantly I removed my cock from the snug warmth of her vagina and we cleaned up, got dressed, had a quick kiss and left the building. It was quite late so I phoned a friend to get the name of the bar they were in, and the homeless lady (I never got her name!) took me to a taxi office. We hugged, I gave her some money for food and wished her all the best and said goodbye. I still think of her and hope she's doing ok.
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Old 04-22-2011, 03:08 AM   #2
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Pretty good story!
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Old 04-22-2011, 12:52 PM   #3
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I second that El Sauve , it is a very good story .... without or without the sexual detail it would remain a good story because its well written and the subject matter and the person involved is interesting in itself . Well done to the author !
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Old 07-22-2011, 12:12 PM   #4
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Very good story. hot and easy to read.

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Old 07-29-2013, 10:58 PM   #5
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Awww, I love your stories. Your a very good writer
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