“Oh, well, I better leave you alone then, the last person you want to speak to is another man”, I replied turning to leave.

“No, don’t go, please” She begged me, “I don’t hate men, just my asshole boyfriend. Can you stay a while?”

“Ok, but not for long, as I’m sure you want to get home soon”

“Not really, I don’t care if I never go home again. Come sit why don’t you” she asked, moving over so there was room for two.

I sat down thinking I hope I don’t get 3 hours of blah blah bah from her. A quick chat to cheer her up and then I’m out of there.

For the next 30 minutes she poured her issues out as I tried to stay awake. The typical bullshit, the two went out for dinner and dancing, and the guy treated her like crap and stared at all the other women. Hell, we all do it.

“Can you do me a huge favor,” she asked me”, and walk me home, it’s not far from here. I really don’t want to walk home alone in case he’s there.”

“Ok, but only to your front door, then I’m going home too”

So off we went. But we had only walked about 5 minutes when she stumbled, and fell over towards me. I caught her, but in the process I grabbed her on her breasts. They weren’t very big, but boy did they feel nice. As she regained her composure, she grabbed my hand, and said it would make it easier for her to walk if she held my hand.

About every 20 meters or so she would half walk into me, half hug me as she tried to walk home. I was starting to get a little excited by all the touching, and by the time we got to her street, I had a full on boner in my pants. I couldn’t wait to get rid of her and get home and have a big wank.

We got to her house, and she stopped, turned to me, and said “Thank you”. She leant in to give me a small kiss, but once again stumbled, but this time we both fell over on the ground, laughing. She didn’t miss a beat, straight away she started kissing me full on. Her tongue was playing tonsil hockey with mine in no time.

“I think you’d better come inside with me and help me get back at my boyfriend” she stated through a half kiss, half mumble.

“And how do you think I can help?” I asked, cheekily.

“I’ll show you, I think you will like it….” She slyly said as she got to her feet, and walked to her front door.

Once inside it was lighted so I finally got a good look at her. She wasn’t too bad at all. I’m only 23 years old, and average. She looked to be at least 35, but in good shape. I’ve seen better, but I wasn’t complaining, a fuck’s a fuck. Right?

We closed the door, and she was all over me again, dragging me to I think her bedroom, while she was exploring my body with her hands. Her right hand moved down and grabbed my dick, which was now at full mast.

“mmm, somebody feels happy” she said as she took her top off. She wasn’t wearing a bra, no wonder her breast felt so good, there wasn’t that much material between my hands and her tits. Her nipples were hard, and very long. I grabbed one tit as I leant over and bit her other nipple.

She cried out in pleasure, and said “Get the fuck to my bedroom now!!” She pointed to the door at the end of the hallway and I walked quickly to the door, opening it and gesturing like a gentleman, offered the room to her.

She walked in, while throwing her pants in my face. She turned the light on, and moved to her bed. She sat down, and gestured for me to follow. I walked over and she grabbed my pants, undid the belt, and dropped them to my feet. My hard on was straining to get out of my briefs. She rubbed me with her hand, and said “I can’t wait to taste this…. It looks delicious…”

“Why don’t you stop talking, and try it out then,” I said, wanting to get into as quick as possible.

She reached in, and took my cock out, slowly wanking it as she brought her face closer. I could feel her hot breath on my cock, which made it twitch. Fuck I wish she’d just suck on it. Instead she just kissed the end, and slowly licked up and down my shaft. To heel with this I thought, I grabbed her hair, aimed my cock at her mouth and thrust my hips forward. She opened her mouth, and in I went.

Heaven!!! Her mouth was both hot and very wet. She slurped down my cock for what felt like an eternity. But after what was only 2 minutes, she told me to get undressed fully, and fuck her went cunt. She didn’t want to fuck around too long.

So I took my shirt off, stepped out of my pants and briefs, and climbed onto the bed. I grabbed her pussy with my left hand, and stuck 2 fingers in. She must’ve had some kids, because she wasn’t very tight, yet she was very wet.

She lay on her back, and I got on top of her, and pointed my cock at her moist wet cunt. There was no slowly entering; I just thrust it in straight away. She moaned with ecstasy, and grabbed at my shoulders, pulling me closer. We kissed passionately while I began pumping away.

I was drunk, and very excited. I hoped I wasn’t going to last long. Really, I didn’t want to, I’d hate for her boyfriend to come back and kick my ass. So I started pumping harder.

“That’s it baby, harder, fuck my cunt harder.” She yelled at me. So I did.

I lifted her legs up, folding her nearly in half, to make her pussy tighter, and pounded away. I was starting to sweat, and her fingernails were starting to hurt my back, but I didn’t care, I was having too much fun.

After about 5 minutes of furiously fucking her, I realized I wasn’t going to come as quick as I would have hoped. I had to ‘spice’ it up a bit.

Boldly, I told her I was going to take a bit longer than I thought, and did she have anything else in mind?

She whispered “Stick it in my ass then, that should do it, my boyfriend is always complaining I don’t let him do it, so you can. Don’t be polite about, just fuck it!!”

I love fucking women in the ass, so I dove at this chance. I spat on my fingers, and stuck one. Then two into her ass, to lube it up a little. She liked this, and grabbed her ass cheeks to spread her hole a bit more. I moved myself to enter, and pushed in, slowly at first, and then pushing all the way in.

I pulled back out, and then as hard as I could, I rammed back in.

“Wow, maybe I should have said be gentle. But fuck that feels good, keep going, come in my ass, and hurry!!” She cried to me, as I started pistoning in and out as quick as I could.

Her ass felt so tight, and I could start to feel myself getting closer to cumming.

“I’m gonna cum in a minute” I said to her, as she grabbed my nipples and pinch them, it fucking hurt, but it made my cock get harder, and I rammed faster.

And then it happened, I started to come, My eyes felt like they were going to blow out my head as I screamed an awesome orgasm, and kept fucking her until I couldn’t keep the rhythm any longer. I collapsed onto the bed, breathing heavily.

“Ok, you’ve had your fun, get out of here” She said. Oh, gee thanks, no after sex kiss or anything, just get the fuck out. She was treating me like I’d treated some women. Bitch. I guess that’s how they feel.

I got off the bed, grabbed my clothes and started to get dressed. She just lay there on the bed, lit a cigarette, and said to me “You’re pretty good. But you didn’t make me cum. SO, here’s my business card” She grabbed something from her bedside table, and handed it to me.

So I get to do her again, sweet. I walked out of the bedroom, and out the front door. As I was walking down the street, I spotted some guy walking up the footpath, and past me. Out of curiosity I turned around, and sure enough he turned into the ladies house, and grabbed his keys and opened the front door, and went in.

Wow, that was lucky, I thought as I walked home, smiling and thinking of when I will get the chance to see her again……….

(me) truth or dare?

(Cindy) dare

(me) I dare you to lift up your shirt

Cindy blushed at first but didn't hold back as she lifted up her shirt showing me her small boobs with hudge nipples and now it's her town.

(Cindy) truth or dare?

(me) Truth

Cindy protested saying that's not fair so I took a dare.

(Cindy) I dare you to lift up your shirt

I did then it went even further

(Cindy) I dare you to show me your penis

Being shy I hestitated but then showed her which at the time was hard and so it was my turn.She took the dare again.

(me) I dare you to show me your vagina and ass

Oh my did she ever.

It went on like that for us for a couple of years before we got bolder at the age thrt-teen when I lived in a new house that had the oldstyle basement with the cellor door outside as we went in. She was talking about looking at her dad's porn mags which showed a man in a woman's ass and she told me she wants to try that. Not having any sexual experience I didn't think that was possible but I found out that day it is and been hooked on anal sex every since. 

The basement had stone brik walls with a dirt floor and we were sitting on a blanket facing eachother. I reached for her boobs carressing them as she reached for my cock stroking it and we kissed on the lips open mouth with our tongues exploring eachother. Shen then unbuttoned and unzipped my pants pulling my hard cock out and she touched the head with your tongue. Never experiencing anything like this I jumped and she looked up at me saying "relax." Guessing from her skills, I figured she had done this before because it felt damn good for a blowjob and I couldn't help what happened next as I shot my load into her mouth. Thinking it was over but not by a long shot as she clamped her lips down my cock firmer and swallowed my cum to the very last drop. Wanting to return the favor I asked her to lay back which she did legs spread, I layed on my stomach and imediately started using my tongue on and in her pussy, of course I wasn't doing it right at first but she was patient with me letting me know when I was touching the right spot as she came hard with her hand over her mouth trying to muffle her screams. Then outside her parents were calling for her, we both smiled at eachother , got dressed quickly and I seen her off with her parents.

The next time she came over with her parents, we immediately went to the basement kissing and touching eachother again. We both admitted to eachother that we missed eachother and been looking forward to our time alone again. She then got a smile on her face, I asked her why and she said "you remember shooting stuff in my mouth and I swallowed it?" Of course I remember, how does a teen boy forget something like that? She proceeded to say "I want that to happen again but in my....ass." Of course I was puzzled not knowing how my cock would fit in such a tiny hole but must admit the thought did turn me on as I felt my cock hardening. 

I spreaded out the blanket as she was pulling her shorts down along with her panties, then got in doggy position and looked back watching me pull my shorts down as my cock sprung out in the open. Smiling at the site she said "I want to feel it in my ass, please." Not sure what to do, I asked how the couple did it in the mag and she instructed me on what she had seen. So, I'm on my knees behind her admiring her ass while bringing my cock closer to her asshole and we both gasped as the head of my cock disappeared into your asshole and since we had no lube, I took my time when she asked me too until I was finally balls deep as we both are panting heavy and she tells to go slow at first which I did. Both of us panting even harder as it was feeling good for both of us I was by now fucking her ass faster. Cindy moaned but in pain, instead with pleasure and talked dirty to me which she didn't need to as her ass was feeling good taking my cock but her dirty talk did add to the good feeling we were experiencing. I grabbed her hips pounding my cock in/out, in/out of her asshole and she was matching my every thrust with her moans, my heavy breathing and sounds of our bodies slapping loud enough for us to hear.All this became too much for me as I stopped moving as so did she while enjoyed the feeling of my cum filling her ass up. By then she was laying on her stomach, I was resting on her back with my cock in her ass pumping load after load of cum deep in her ass and we managed to kiss with my cock still in her ass.

After getting dressed, we heard her parents calling for her as we snuck on last tongue filled kiss and as we made our way outside, both her parents and mine were standing there with a look that told us we were busted and of course we tried to deny anything they were accussing us of.  It's been a long time of her parents not bringing her over which was driving me crazy, I wanted in Cindy's ass again as she later told me she wanted it again much as I do but that's a different story.

 If you want to read our second encounter, give me your feedback on this story that acctually happened.