The next day, I was walking down the hall towards an empty bar when I overheard two girls talking. One was Ashton and the other was one of the owner's daughters (Candice) who also worked in the bar. "He's cuter than she described him" said Ashton, but who were they talking about . . . "I would deffinately not mind letting him be my first." she said.  Their conversation carried on to something else and never went back to that subject so I went on around the corner to say hey.  "Well speak of the devil" said Candice. Obviously, neither of them realized that I had overheard them, but I wasn't telling.  Granted, my mind was quite unsettled for the rest of the day and that night.

A few days later, Jessica approached me with the question, "Is there anything going on between you and Ashton?"  No, I said Honestly (not yet there wasn't). She beleived me because she can tell when I'm being honest and when I'm lying.  "Why would you ask something like that?" I said.  "Well, I was just making sure you two weren't having too much fun without me."

I almost jizzed in my pants a couple of times over the next few days just thinking about what she could have possibly meant by this.  Yes, Jessica and Ashton are both that hot, but I never would have thought . . .

Back to the story.  One day the next week, Ashton and I were closing together me outside and her in the bar.  All that day we had been flirting and hinting at what we wanted, but we both knew nothing like that could happen between us. I finally finished up my work outside and walked up to the bar to keep Ashton company while she closed down the bar.  The bar was empty. No customers, no tired golfers, no Ashton.  I looked around to find her but couldn't. I checked the parking lot to see if her car was still there and noticed that not only was her car there but so was Jessica's. Hmm . . .

I walked back inside to use the phone and call Jessica's cell. Just as I stepped around behind the bar and reached for the phone I tripped and fell flat on my face.  I looked back to see what it was that I had tripped over and saw a pair of Khaki shorts. They were the shorts that Ashton had been wearing that day. Most guys know what I'm talking about when I say, super instant hard-on plus tingly horny feeling.  I then noticed under the counter and white bikini top.  This is Jessica's I thought, but that doesn't make sense she only wear's a bikini when she's . . .

When I got to the pool I couldn't see anything till my eyes adjusted, but then I saw them.  Ashton was laying on the stairs of the pool with Jessica straddling her kissing her chest. They were both topless.  Jessica turned to look at me and said "bout time you joined the party."  She went back to kissing Ashton as I jumped into the pool with half of my clothes still on.  As I waded over to them Jessica reached around behind her and pulled on her bikini bottom never breaking the kiss with Ashton.  Yeah, I knew what she wanted, damn right she was gettin it.  I pulled the bikini bottom the rest of the way down as she stroked my already full hard on with one hand and plunged two fingers into Ashton with the other.  She pulled my cock right up to her anus and positioned it at her asshole. I pushed and slowly sank into her still tight ass.  She came within a few strokes and I then noticed that Ashton had been rubbing her clit when she reached up and started massaging my balls.  Put it in my pussy" said Ashton.  Jessica still never broke her kiss with Ashton as I pulled out of her, put two fingers where my cock had been, and plunged into Ashton's pussy.  She moaned the loudest sexiest moan I had heard in a long time and came quickly as Jessica was still kissing her chest and rubbing her clit as I slow fucked her.

After Ashton's orgasm subsided Jessica climbed off and grabbed both our hands and dragged us to the pool house.  She pushed me up against the wall and went straight down to my cock.  Ashton stood behind Jessica and bent at the hip to caress the top of my cock while Jessica was on her knees putting my balls in blowjob heaven.  I blew my load pretty quickly though not many guys could have held out long with that kind of attention.  They kept on sucking and licking and kissing, keeping my cock from ever getting soft.  Jessica then moved around behind Ashton as Ashton was halfway deep throating me and began playing with Ashton's clit. She then moved her hand up and started rubbing her asshole though I wondered why she didnt put a finger or two in. I watched as Jessica then sat up and staring into my eyes began licking Ashton's asshole. Ashton was now moaning on my cock as she neared her second orgasm.

Jessica then asked "Okay Ashton I think he's ready, are you ready." I was confused, what more could there be.  Jessica then explained to me that Ashton was an anal virgin and wanted me to be her first.  I blew a load down Ashton's throat as Jessica finished explaining this situation.  Ashton kept kissing and sucking. Jessica sat up again and dove her tongue into Ashton's pussy. She let out and long moan that shook my cock to life again. She kept on moaning and I couldn't help but begin to move my hips with her oral strokes on my cock. Jessica slowly moved her hand up to Ashton's asshole and started probing her hole with her index finger.  She wiggled her finger around and worked an inch into Ashton's hole while still tossing her clit with her tongue.  Ashton moaned louder on my cock.  Jessica then backed off and inserted her index finger into Ashton's pussy to get it wet. She moved it right back up to Ashton's asshole but this time slowly pushed it all the way in and began thrusting in and out.  Ashton's knees began to buckle but she continued her work on my cock.  Jessica then repeated this with two fingers and Ashton moaned louder and longer. Jessica really starting pushing and twisting her fingers and Ashton could take no more, she had to back off my cock and kneel down. 

Jessica then said to me, "Okay, your turn honey". Jessica then laid down and spread her perfect legs. She pulled Ashton right down on top of her and Ashton went to licking Jessica's clit. I moved around behind Ashton and repeated what Jessica had done with two fingers. Ashton moaned the most beautiful moan I've ever heard and had a third orgasm, yet she kept on working on Jessica's clit. Jessica then had an orgasm and Ashton moved up to straddle Jessica.  I then witnessed the most passionate kiss I've ever seen. I couldn't help myself and had to do it then.  I moved up close behind Ashton and again plunged my cock into her gorgeous pussy, and massaged that beautiful ass of hers.  I pulled out and Ashton quickly looked back at me and said "Please start easy."  She watched as I aimed my cock to her hole and began to push.  Jessica reached around her and spread her ass for me.  Her asshole slowly gave way to my decent sized cock.  "oh, god" she said as the head of my cock disappeared into her ass. Jessica reached under her and played with her clit as they resumed their kissing. I kept pushing until I got half of my length in and Ashton began pushing back on my cock. She wanted it inside of her.  We both pushed as Jessica moved to fingers to her vagina opening. Jessica plunged her fingers in and caused Ashton's anal muscles to release and I sank into her. Her anal muscles then naturally contacted tight around the full length of my cock and I blew a load deep into Ashton's ass.  I began pushing to keep my cock from receding and kept it hard.  When I was fully hard again I pulled out an inch and plunged back in as Jessica was now fucking Ashton's pussy with three fingers. I pulled out and stroked longer and longer strokes until I was slowly thrusting the full length of my cock in and out of Ashton's extremely tight, but now wet with come, asshole. "Oh yeah baby fuck my ass, that feels so good. Go deeper."  Ashton's was screaming and bucking her hips as both of her holes were being fucked.  I blew another loaded into her and she began to orgasm but neither of us nor Jessica stopped the pounding. We slowed and sped up and slowed and sped up in this position until Ashton had another orgasm.  She roled over and Jessica climbed on top off her and I sank into Jessica's ass as Ashton finger fucked Jessica's pussy.  I blew another load into Jessica's ass, and she and I collapsed on top of Ashton.  The three of us made out for close to an hour until all three of us feel asleep on the pool floor. 

I woke up a few hours later and looked up at the poolhouse clock. It was now 230 am.  I looked over at Jessica, who was still asleep, and then to Ashton who looked up into my eyes.  We both knew what we wanted.  She spread her legs wide as she was laying on her back and pulled me by the hand over to her. I climbed on top of her and started to push my cock into her pussy.  She pulled back and grabbed my cock. "No" she said "wrong hole"

(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.