Ahh Yes, Mandy… She was a really strange one.
I ran into her at the bar pretty early on in my bartending days. I had slept with only a few girls from work at this point, and was sleeping with Laura the MILF nearly every other day so I thought my needs were pretty well covered. Still, I was always looking for the next thing, and as it would turn out, she was it. Mandy was in college, and would come to the bar most Tuesdays with some friends for whatever the Tuesday night special was. She caught my eye pretty much the first time I saw her. I don’t remember exactly why, but some girls had a look or a vibe that I would pick up on right away. Shy, awkward, maybe just a little different, I don’t know exactly what it was with her, but a combination of those things led me to her, and I went for it.
I noticed that very first night that she was the shy one in the group, always avoiding the drunken frat boys that wandered from table to table trying to get their dicks wet. She just didn’t fit in. If everyone was wearing shorts, she’d be the one in an 80’s dress. I can’t quite describe it, but she was awkward, both socially and in her mannerisms. For some reason these were the girls that caught my attention, and the more I watched Mandy, the more I knew I wanted her. I don’t know if there is any truth to it or not, but I always felt that these types of girls were easier to get. So my attraction to this type of girl may have helped me in my many quests as a bartender.
I made sure to make some small talk with the girls at her table and certainly made sure to give her extra attention when ever chatting with the group. This is a kind of subliminal signal that chicks pick up on. I don’t know if it worked, but for the next few visits I made sure to repeat the task. Each time she came in with her friends, I chatted them up a little more, and of course her a little more as well. I gave them a free round from time to time and the magic started to work. I never came on too hard, as I’d seen how quick she was to turn down any offers from other guys, and instead used humor to win her over.
This went on for a while. During that time, I managed to start fucking one of the new waitresses, but continued to pursue Mandy as well as many others. Finally, one night she and her two friends came in and sat at the bar, the first time they had ever done so. I saw this good fortune as my opportunity to really lay it on strong. I knew that this was likely my best chance to bone this "Nice Jewish girl” I’d been getting to know, so I started to talk with her. I don't really remember that much about the conversation, or for that matter her back story, but I do remember that I didn’t get her home that night. In fact, she turned out to be quite a tuff nut to crack. Awkward to talk to and hard to read, but good looking enough to continue trying. It took 2 more weeks of trying and prying before I finally convinced her to stick around till closing.
And that's exactly what she did. Her friends peeled off about 11pm like they usually did, but on this fateful night, Shy little Mandy finally stuck around. Like I’d learned with other girls early on, I’d been feeding her and her friends free drinks for hours, and had been laying on the charm as hard as I could. On this night, it finally paid off. They left her, giving her the “Nod of approval” that these girl groups often did when they knew there would be hooking up in the near future.
The moment they left two things happened. I became sure I was finally going to get to fuck Mandy, and Mandy in turn got super shy. She clammed up and wouldn’t even make eye contact. I blew this off and continued to act the part. I knew she had to be wasted, as she must have had 4 drinks before her friends left at 11, and I know I served her at least another 3 before we closed shop at 1:30am. Even with all that booze, she still seemed timid and shy. Normally a girl would be shirtless and screaming for attention with that many drinks in her, but not Mandy. She stuck around hardly speaking, but still drinking, waiting until 2am for me to get off, and after working up to the big moment, I asked her if she wanted to come back to my place and hang out. She said yes, and at that moment, I knew the night was already won. Strangely the ride home was nearly silent. I’d talk, and she’d giggle or offer a word or two, but the conversation was almost nonexistent. Usually once a girl was headed to the house after a pickup, they would nervously chat up a storm, but not Mandy. She for the most part fidgeted a bit and was silent.
Anyway, after all the weeks and months of working on her, I finally fucked her that night, and as luck would have it, my pervert of an Indian roommate was in the living room watching the whole thing on the TV as he often liked to do when I brought a girl home. About a year earlier he had convinced me to let him install a broken, and somewhat massive VHS camcorder in my room that was attached to a 50-foot run of cables to the TV in the main room. Why, and how he had convinced me to allow him to do this is something for another story, but using this setup, he’d seen me have sex with at least 5 or 6 other girls on that TV, many of them much more than once. He always loved it when a new one arrived home. We walked in to my tiny place and noticed him sleeping on the couch. I used this as an excuse to move Mandy quickly down the hall to my bedroom after grabbing a few beers from the fridge. Of course, as soon as the door closed, Larry was up and the TV was on so he could watch the show.
Normally once I was back at my place, I’d drink a bit and slowly work to get the girl in bed. Mandy was tired, and visibly wasted, so I quickly moved to the good part. She offered no resistance other than her normal shyness. On the bed, I quickly pealed her out of her cloths. All this time I had waited to finally see her naked, to finally hold her body, to finally fuck her, and here I was. She was almost exactly what I had imagined. Her 5-foot 1-inch-tall body, sported just a little extra weight, and it was hanging tightly to her in all the right places. Super thick, tightly curled dark brown shoulder length hair led to a smooth back and a few freckles as it sloped down to her curvy round ass. What an ass it was, round firm, and sporting a tan line that would make anyone hard. This then led down to a pair of semi-muscular legs. Short for her height, but attractive never the less. Looking down at her feet, I noticed she had bright red painted toenails to match her fingers. Turning her over, I found her pussy nearly fully obscured by a huge untrimmed patch of matching curly hair covering In the mid 90’s it was still common for a girl to have bush, but Mandy’s looked like it had never seen a pair of scissors. It turns out, it hadn’t and as the weeks went on, I helped her make some adjustments down there. Her olive skin tone, dark features and toned body drew me in and I’m sure my cock was throbbing as took it all in. The only real surprise of that night as taking off her bra and realizing that her tits here a full cup smaller than I had imagined. It wasn’t the end of the world, but I was shocked to see a set of very firm B sized tits pop out when I had totally expected a larger c set to be hiding in there. I remember how hard it was to get her naked that first night with the lights still on, and how timid she was in bed that first night. She was clearly inexperienced and it showed. It wasn’t until many nights later that I came to realize just how inexperienced she really was that night.
I slid in between her legs on the bad and grabbed her tits, cupping one while sucking on the other. She lay nearly motionless and made no sounds as I continued. Her nipples hardened as fast as my cock, and I decided to wait no longer. With another move up onto the bed, I pushed into that patch of fur, and slid into her. I fucked her for a total of about 20 minutes that night, and while not a wild ride by any means, I made sure to make it count. What I found that first night was, what is still the tightest pussy I have ever fucked. I mean it. It was almost harder to get my cock in her pussy that first night, then it was to get it in her ass months later, but more on that later. Surprisingly she never asked me to put on a condom, and I certainly never offered. I fucked her missionary that night, much to the dismay of my roommate watching it all from down the hall, but I did pull out and cum on her tits and neck, with just a little splash making it to her chin. Her reaction was priceless and I heard a muffled laugh from down the hall from my roommate as it all went down. Right after I finished, she used the bathroom and in no time we both were out.
The next morning, I took her to her dorm and dropped her off. I was honestly wondering if I’d ever hear from her again as she never really seemed into it, but she called the following night and from that point on it was a pretty regular fuck fest for the next month or so. She’d come to work, or I’d pick her up at the dorms and we’d hook up. Every time we hooked up, I’d get her to do more and more. While still very shy in bed, I was able squeeze some of the reasons why out of her. It turns out she had only been with one other guy, and they had only done missionary, and had only had sex 4 times. To me this made her damn near a virgin! Now this explained a lot, and after learning this info, I made sure that our fuck sessions got longer and longer as I convinced her to do more and more things. Cowgirl, doggy style, reverse cowgirl, side fucking, shower fucking, public fucking, back seats, front seats, behind the bar, in her dorm, and more. I fucked her two, and sometimes three times in a day, and sometimes (unknown to her) She’d be the second girl I fucked in any given day, having fucked Laura at lunch before fucking Mandy after work. As the days and nights went on, I ran into some hard lines she just wouldn’t cross. She consistently refused to suck cock and it drove me nuts. I’d never been with a girl that didn’t give head, or at least a hand job, but she refused to do either. I’d ask her often, and then use the “No” as a reason to try something even more crazy in bed to see if she’d change her mind.
Looking back on it all, I think she really truthfully hated all of it. If given the choice, she preferred to stick with missionary, but after the second or third time with her, that was just not enough to get me off. I was still banging Laura the MILF who was wild in bed and was fucking at least one other girl on a semi-regular basis that was much more fun in bed as well, so in order to stay with Mandy, I felt I needed more.
And then this happened.
While all this was going on, and it was only maybe 3 or 4 months, Mandy thought we were boyfriend and girlfriend right from the start. Once I had learned this, I had just decided to let her go on believing that. Like I said she was inexperienced, and hadn’t even fucked anyone other than missionary until me so I wanted to keep her going until I had really had some time to open her up. It was strange maybe, but that was who I was back then.
Anyway, after like a few months of fucking her, and letting her spend maybe 1 night a week at the apartment, I was getting bored with her and the limits she had set and started thinking of just blowing her off unless I need to blow a load. With 2 others on call for such things, Mandy started to fade from the picture.
It was about the time I had decided that I was nearly done with her and had already started plotting to send her firmly to the side lines that she comes over and she asks when she's going to get to move in with me full time! Guys, I didn't want to run her off altogether, but I was really bored with her, and there was literally no chance I was ever going to let that happen. Still, I didn’t want to lose her all together so I listened to her vent about wanting to get more serious. She talked about moving in, getting married and damn sure she even talked about having kids! The whole time I’m mostly tuning her out, somewhat shocked at what was unfolding.
Then I got an idea….
Instead of kicking her out, or breaking her heart by telling her she couldn’t move in, I decided to play along. I let her talk herself out, and then I told to her about how much I liked her as well, but that I was frustrated. I told her that even though I liked her, we had hit a wall in the bedroom and that I needed more in order to commit. I explained that I couldn’t see myself marring a girl that was a “One hole girl”. She sat there with a confused look on her face, kicking her leg up and down, arms crossed, clearly not understanding my wants. I could see didn't get it, so I explained the whole blowjobs and anal thing, and then went on to explain that everyone else that I had dated gave it all up. Mandy hated that I’d been with so many girls and was experienced, and I think that may have played a bit in my favor. I went on to tell her that since she was so sweet and that I really liked her, if she really wanted to get serious with me, I’d consider it. I told her I could learn to do without one of those things, but in return, she'd have to do at least one of them, and on a fairly regular basis in order to keep me satisfied. She just sat there, shaking her head slowly as I went on to tell her in many different ways that I just couldn't see myself with someone that didn't do anything more than just plain old sex to keep her man happy and that I hated to lose her, but that was where I was at. Looking back, I’m sure she was totally shocked by all this. In her mind she’d pushed every limit in bed with me. She’d fucked so far out of her comfort zone there wasn’t anything left that she’d considered.
When I was done with this enormous pile of bullshit, I waited for her to get up and leave, but instead, this was a moment in my life that changed me. This is the single moment that made me a bartending freak.
I figured Mandy and I were done, but I had played my cards hoping against hope that maybe she’d suck my dick a few times before I finally gave up on her. To be honest, the anal option was just there as a “Hell no” thing that would suddenly make blowjobs look much more reasonable.
So I sat there staring at Mandy, waiting for her to leave. She said nothing, kicking her leg up and down, arms still crossed staring at the same TV that Larry had watched her fuck on many times without ever realizing it. Then, after a long motionless pause, she stood up. I thought for sure my gamble was lost, and she was going to flip out and leave, but after what felt like a full minute, she turns and tells me “I just can’t imagine putting a dick in my mouth, but if you want me to have anal sex, I will”.
I shit you not, can you fucking believe it? Who in the hell would choose an ass pounding over a little cumshot in the mouth??? I sat there for a moment fucking stunned! Every time I had fucked a girl’s ass prior to this and it had only been a handful of times, it had taken a LOT of drinking and a lot of trying to get it done. But not here, not right here in this moment with Mandy. I tried my best to soak in what she had just said. My brain stumbled over the words over and over. She was like “OK, Fuck My Ass… Boyfriend.” I was in shock, and as it turned out, this was the girl that really started the whole anal conquests thing going for me. From this moment of my life on, it was ass fucking all the way.
Once my tiny horny brain finally crunched the numbers and realized what had just taken place, I moved quite quickly to “Seal the deal”. As Mandy was already at my place when we had this conversation, I had her in bed, ass up in less than 2 minutes. No exaggeration!
I couldn't even contain myself. Not more than 10 minutes ago I was done with this chick, and now I wanted her worse than anything on earth. I didn’t beat around the bush or talk about anything more after she made that statement. Once I had let it all soak in, all I said was “Ok, really? Let’s do it.” I waited for just a moment for her to change her mind, and when she didn’t, I stood up, grabbed her by the hand and walked her down the hall into my bedroom. A large part of me really thought I was just going to get her to call her own bluff and maybe and up with some second-rate head before dumping her, but she wasn’t bluffing.
I had her out of her clothes so fast, I nearly tore her panties pulling them down. Fully naked and still standing next to the bed, I then removed my own outfit in another minute all the while explaining that it might hurt a little. Her average body and b cup tits suddenly looked great as I started into her eyes looking for her to fold. She didn’t and in another swift move, I put her on the bed in the ass up doggy style position, crawling in right behind her. I stared down at her shapely ass, and realized this was going to be fucking awesome. I sat there for a just a moment and soaked it all in. She said nothing as I grabbed her thighs to pull back on her as I used my knees to spread her legs apart so she was in the perfect spot for anal. With her legs out to the sides, and her face down in the pillow, her ass stared up at me. A pretty pink button just waiting for me. I waited no longer to make my move.
Guys, I tried to spit in my hand to lube up my cock a bit, but I was so stunned, by the turn of events I could hardly get any spit. What little came out of my mouth missed my hand and landed on her ass cheek. It sat their glistening as I tried to work up some more, but it was hopeless. So, I took one finger, and tried to scoop it up, that was all I could get, and it barely got the tip of my dick wet, I remember swirling my finger tip around the tip of my cock trying to get it wet enough to go in. That tiny bit of spit swirled around with a bit of precum already oozing from my rock-hard cock was all I could offer her. It was a useless amount of “lube” for a first time anal, but I was fucking going for it! I took one hand and grabbed my shaft, and used the other to hold her ass in place and gave her ass a quick push. The good news was that with so little lube, my cock stayed right on target, the bad news is it must have been a bit rough at first for her as she bucked up and forward a bit and let out a gasp. I know I should have fucked her pussy a bit to get things wet, but I just had to be in that ass of hers. Moving myself forward a bit to lock her back into a good spot, I plunged forward with a second harder thrust, her ass opened up, and in went my cock. The lack of lube might have made it hard to break her ass open, but it gave way to my insanely rock-hard cock and the shear amount of determination Inside of me.
Although I told her relax, her ass felt as tight as a virgin ass should be. She clenched down with all her strength, gripping my cock like a fist. I stopped at about 1/2 way in, and let it sit there for a moment, asking her if she was ok. Like a trooper, she just said "It’s Ok". As I felt her as contract and grip even tighter. I knew she was lying, but I couldn't hold back any longer. From that moment on, a tiger could have been chewing on my leg and I wouldn’t have been able to stop. My cock was rock hard, and it was ready to play.
That was it, I started fucking her ass. 1/2 way in for the first few strokes, as I could feel her body tense up in my hands with every plunge. But then after less than a minute of trying to go easy, I just couldn’t hold back. I felt the need to really fuck her. I pushed my cock in until it hit a turn inside her and then pushed past it. She jumped back a little, and her reaction to that deep thrust made me even crazier. I was in tune with her body, I had full control. I started to ram my cock in and out of her ass like it was the last day of my life. Soon I was fucking her at a speed and pace that only a young man can sustain, I jack hammered away at her ass slamming myself in as deep as I could and then I'd back it all the way out a few inches then slam it back in until it was "balls deep". It wasn’t long and after that I pulled out a bit too much and missed her ass, instead slamming into her vagina. I didn’t care, I was going full throttle. I’d pull back out after a few strokes and plow back into her ass. This went on for a while. She never said a word or made a sound, but with every stroke I could feel her body that was clasped between my hands on her hips tense up and then release, tense up, and release as I pounded her virgin ass time after time. This went on for at least 10 minutes until the first time I had to stop.
I was so totally lost in the moment. Sweat pouring off of me, that I had to pause to catch my breath. At this point, the building could have come down, and I wouldn’t have noticed. I was so focused on watching my dick slam in and out of her ass, that nothing else mattered. Back to it I went with a new found vigor, and I savored every moment of every stroke. Every time I felt as if I was going to cum, I’d ram my cock in as deep as I could go and stop, letting the throbbing in my balls and shaft subside while catching my breath before starting the process again. Sometimes I’d lean in over her body and grab her hanging tits, or I’d pull out for a moment before popping back in. She’d jerk back a bit, but in no time, I was back at it again. It took over 20 minutes at nearly top speed before I began to feel her loosen up. The writhing in my hands started to settle out, and she just began to take it like a champ. I was soaked in sweat and completely exhausted from the work, and the throbbing in my balls had long ago become almost painful. I knew it was finally time to cum. If it was even possible, I managed to fuck her even faster, the bed shaking rapidly as I built up for the final time.
Now Mandy wasn't on any birth control, so I always had to pull out when I fucked her. Not this time. As the throbbing in my balls and the tightness of my cock reached critical mass, I rammed myself as deep as I could with my balls firmly pressed against her pussy, and blew a massive load right in her ass, pumping load after load of hot jizz deep in her. It felt as though I had built up a gallon of cum while fucking her, and it was one of the best orgasms I ever had. The room was spinning as I pumped my last drops of cum into her, and then I sat motionless with my cock still throbbing, deep inside of her.
That was it. The moment had passed, and my brain started to return to normal when I was finished. I pushed off of her, and looked down to see some of that load leak out of her ass right down over her pussy lips. I breathed deeply, and asked her if she wanted to shower. She could hardly speak, but was as nice as someone that just got a hundred-dollar tip. She nodded, and hobbled to the bathroom with me. We showered, with me telling her how great it was, and how I couldn't wait to do it again! I waited for her to complain, so at least comment on it, but she just stood there stunned, looking at the shower floor.
When we were done, we crawled back into bed, and passed out. The next morning, I woke up with a hard-on, and a smile on my face. Mandy had really figured out how to please a man!
From that moment on If I thought of Mandy, all I could think about was her ass.
Hell maybe she was right to choose anal over blowjobs. I never remembered the blowjob from last night as greatest, only that I came, and I didn’t have to work for it. Don’t get me wrong, I love a good blowjob, and a girl that swallows is perfect, but this...This was nice. I remember every ass I fucked, and every time I fucked it. The way the girls responded to my thrusts, the feel of it, the tightness, the heat. Mostly I remember the start of it. Like opening a can of beer, the first plunge. That was it.
I woke her up that next morning, and after some sweet talk, I was back in that ass for a quickie. She just laid there on her side as I stuck it in her pussy to get it wet, and then with little warning, switched to her ass for a little extra credit ass fucking till I came, and when I came it was deep in her ass again. After a few minutes of post anal sweet talk, she got dressed, and then it was off to class for her, with a load of cum in her ass, and a nap for me.
Now guys, I never did let her move in, but I delayed "dumping" her for at least another 3 months. Mandy had given me a reason to be her “Boyfriend”. Her virgin ass! I don’t know how she put up with it. After that first night in her ass, I never took her out, and never did much of anything, she’d just come over after work or school and after some very brief small talk or some TV time, I’d look at her and say “you ready?”. She took it like a champ too. Never complained, never stopped me. I would sometimes go straight to it, never even telling her I was about to fuck her ass, just sliding it In and fucking it start to finish, but most times, since she let me, I'd fuck her pussy, then switch to ass, then back to pussy, and then finish off in her ass. She must have hated to be on the rag as I would always end up having a LOT of free time when she was on the rag, using it as an excuse to fuck her ass daily skipping her pussy altogether. It was great. And I always came in her ass.
I even managed to fuck her ass at the Sears where she worked. I came and visited her one night and ended up with her cornered in a small cleaning closet right next to the break room. I kid you not, I dropped her jeans just enough, slid her panties to the side and gave her what she thought was going to be a quickie. It was, but It was an anal quickie! I spit a little, and gave it one hell of a jam, pop! She’s taking a load in her ass at work. It was so great to help her quickly pull up her pants and get back to work with a load in her ass. It became a somewhat classic move of mine that started with Laura the MILF vaginally, but spread to Mandy’s ass as well as April’s and Kim’s. There was something so hot about watching Mandy working the register while puckering up to hold in my jizz, or watching April as she waddled around the bar serving drinks just moments after taking a load in her ass upstairs in the paper closet.
Anyway…
That was it, a girl who was 60 seconds away from being dumped became the best fuck of my life. After plowing her ass that night and every time afterwards I was a changed man. Anal was something to have with every girl I slept with. Eventually I still had to dump Mandy, as she really cut into my free time with the other bar girls, but I held on for 3 months, putting up with her boyfriend girlfriend shit, and letting her sleep over way too many times. Letting her live her dream while I lived mine.
In the end, I even tried to keep her around as some side pussy, but she told me she wasn’t that kind of girl…
So that's the story of Mandy. PLEASE Comment. I Love to hear what people think of Mandy, her body, her tits, bush, and everything else.
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