Andy’s First Anal Adventure: Lisa

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Hi, I’m Andy, and I’m just a regular guy who has been blessed with strong powers of persuasion. I’ve got a quality, I guess. I apparently know what women want to hear, and, more importantly, I can say it with conviction. Women will respond to flattery even if they know it’s bull, but they prefer passionate declarations. You don’t have to tell them you love them, but whatever compliment you bestow, be it romantic or sexually crude, say it like you mean it. Anyway, enough of my boring philosophy on how to bed the ladies. The point is this: I’ve fucked lots of girls, some of them way out of my league. And somehow, I convinced a few of these women to let me in their ass. These are my anal adventures. And they are true.

No. 1: Lisa

Lisa was such a cutie. She was bubbly, upbeat and bright, none of which explains her attraction to me. Near 5’9, she had a mane of long brown curls, a great smile, long legs and huge, huge breasts. I’ve had other big-tittied girls, but none were as skinny as Lisa, whose 34D chest was accentuated by her slim waist. And between her long legs and slim waist was a delicious bubble butt that jutted proudly from her body without appearing fat.

I met Lisa at a campus party, though she didn’t go to my school. We were both first-years, she at an all-girl Catholic college (really!). After more than 10 years I can’t remember how we struck up our first conversation, but we definitely hit it off. In fact, we ended up in bed together that very first night – the first “first-date-fuck” for the both of us.

From a small town, Lisa had limited experience, but her two previous lovers sounded like real assholes, which helped make me look better. One had even slapped her, which is just plain stupid no matter who the woman is, let alone a sweet cutie like Lisa.

So anyway, a quick word about that first night. It was in the skinny bottom bunk of my dorm room, and I’m ashamed to say it was the first and one of the few times I actually fell victim to a premature ending. I couldn’t help it, though, even through the condom; her hairy brown groin hid a tiny hot hole that literally seemed to suck at my thick dick (one anal lay later described it as a fencepost, though it’s only average length). We did it twice that first night and once more the next morning, her cute pointy tongue occasionally licking pouty red-painted lips between moans. With her big breasts crushed against my thin hairless chest and my arms wrapped around her back, she propped her long legs against the crossbar of the top bunk and quietly urged me on.

We established a nice pattern after that. I would see her usually three times a week and we’d screw twice a visit. It was a freshman’s dream come true. In hindsight, I was a jerk. She came to my school almost every time, and I rarely took her anywhere (neither of us had a car).

But I digress. That summer, I spent most of the break in my new locale instead of going back to my childhood home. I rented a room and met the girl of my dreams. It wasn’t Lisa, but we continued to see each other. One night around the 4th of July we were in my steamy, humid room and pretty-tittied Lisa was riding me. She loved that. I’m great at giving head, but she wasn’t too crazy about it for some reason and couldn’t get off that way. To be honest, that was OK with me because she had a little too much bush for my liking, so our usual was for her to pound away on top bursa escort while she frigged herself furiously until she came, then I’d roll her over and get mine.

Anyway, on this sweaty night her tight pussy pulsated around my cock as she flew up and down, her skin glistening and big breasts bouncing. God, she was hot with her cute face framed with dark curls and those full lips parted. My hands drove her hips up and down and she had both hands buried in her dark crotch, her juices squishing. My hands wet and slippery with sweat, I got an idea. I had ass-fingered three girls before her and two had liked it (or at least put up with it). My odds were good. I slithered a hand behind Lisa’s butt and reached down to where our bodies joined. The whole area was soaking with her excitement and our sweat. As she gasped and pumped, I worked my middle finger in slow circles around her asshole. I gently pressured the center of the hole and the tip of my finger slipped inside after some persistent – but not sudden – pushing. I waited for her to tell me to stop, but she just rode harder, her breathing coming faster and her eyes shut in concentration.

I worked the finger further, my dick jumping inside her from the thrill. Both her lower holes were just steaming. In to the knuckle, I pulled out, then pushed back in. We established a rhythm – she’d ride to the tip of my unit and I’d leave just the tip of my digit in her ass, then she’d fall to the base of my thickness and I’d drive the full finger into her depths. All the while she was playing with her clit, harder and harder. Usually when she came, she would be exhausted for a few seconds. This time, she was damn near comatose. She reached her peak in a quiet fury (old house, thin walls), shook, went stiff and collapsed on my chest, her soft round tits flattened. My dick still twitched hard inside her as I took my finger out of her behind.

Her breathing slowly returned to normal as I played with her long hair and stroked her back. “Oh my god, that was awesome,” she whispered.

I giggled, asking, “Are you OK?”

“Oooohhh yeah,” was her sexy response. And then she said something that blew my mind, something I’ll never forget. “When you put your finger in my anus I felt like a virgin again.”

Holy shit. I always tried to rise above my basic dorkiness, but I’m afraid I failed at that moment. “I’d like to stick more than my finger there,” I said. I know, corny and dumb. But she was too sweet to care.

“Oooh, really?” She was into it. “Well, I’ll try anything once.”

She meant it (and, unfortunately, I never followed up on that declaration). I had a tube of Vaseline because I had planned on talking my high school girlfriend into ass fucking, so I found it while Lisa propped herself onto all fours. She looked gorgeous on her knees and elbows, her back arched and her ass sticking up. Her wild mane of curls hung toward the creaky bed and her huge tits brushed the sheet. I greased my finger and knelt behind her fine behind.

“You’re so amazing,” I whispered soothingly. “I’ve never done this, so let me know if I do something wrong.”

The knowledge that I had never put the wood to an ass turned her on even more. “Ooh, we finally found something you haven’t done,” she said in a sultry voice. “I can’t believe I’ll be your first.”

Now, it certainly wasn’t like I was Mr. Experienced. I had screwed four girls in high bursa escort bayan school before Lisa. Not bad for a geek like me, but not a lot either, and I wasn’t sure why she thought it was novel to do something I hadn’t done. But who was I to argue at that moment?

With her asshole still slightly open from my earlier exploration, my right index finger quickly found a home in her hole. I could hear Lisa suck in her breath as I lodged the digit further inside and twisted it around to loosen her up. Spreading her bubble butt with my left hand, I wormed a second finger into her tightest of tight places. “Ohhh god,” she moaned. “Please go slow.”

Not wanting to blow this awesome opportunity (and trying to be a decent guy), I complied. The whole area was slippery with her cunt juice and the lube, though, and it was easier than I expected. I turned both fingers in her ass and gently pushed them in and out. I had taken the mandatory rubber off at some point (she was religious about that, too) and leaned against the back of her thighs. I was so hard at this point I felt like I’d burst.

“I’m gonna put it in your vagina for a second to get it more wet, OK?” I asked, conveniently forgetting I could accomplish the task just as well with the lube. The feel of her squeezing pussy around my bare dick as her slightly opened asshole winked at me just about made me lose it. Pulling out, I positioned the head of my prick at her other hole.

“Just relax, baby,” I murmured. “You are so beautiful; so hot.” Spreading her ass, I slowly but firmly pushed. She groaned as the tip slipped inside. Arching her back allowed another inch to disappear into her depths, but then I was stuck.

“Wait, wait for a second,” she gasped softly. “Are you almost in?”

I looked down and saw that less than half was up her hole, and she was at the thickest part – the part that’s six inches around. “Um, yeah,” I lied, figuring that was better than the truth for both of us. “Just a little more.”

I pulled out, then again pushed in to the thickest part, then out, then in. She was starting to loosen up, and I leaned over her back, gently took her right hand and guided it to her clit. As she began to play with herself, I again pulled out and pushed in, but this time I didn’t stop, instead forcing some of my girth up her. “Oh god! I feel so full!” she quietly exclaimed.

“Do you want me to stop?” I asked half-heartedly.

She shook her head no. “Just be gentle.” After sawing back and forth a couple more times, I was about two-thirds in. Something in her rectum finally gave way and I sheathed my cock fully to the balls. “Ohhhh,” she moaned loudly.

“Shhh, it’s OK,” I said, stroking her back. “It’s all the way in baby.” God, it was so tight. Hot and moist, her can clutched my cock so hard it hurt. I began pumping in and out while she continued to rub herself, her juices squishing.

“Go slow, please go slow,” she gasped, as my full length pushed her face into the pillow, her giant sweater bunnies flattening on the bed. I did, for awhile. Back and forth, in and out. The room reeked of sex and humidity hung in the thick air.

It was by far the best sexual experience of my young life, and I had been lucky enough to have a few great ones with my ex-girl. Her ass slowly stretched, allowing easier passage for my sausage. Other than those first couple times with Lisa the night we first met, escort bursa I used to be able to hold my come for more than 30 minutes, and this was one of those nights. We had been fucking for at least an hour total, and probably about 20 of that was me up her puckered portal.

Working her clit for much of that time, Lisa clearly enjoyed most of our anal foray. But it must have been sore after awhile. “Are you almost there?” she gasped.

“Can I go faster?” I replied. “I’m getting pretty close.”

She nodded and returned her fingers to her joy button. I immediately picked up the pace, bottoming out hard. Lisa started grunting rhythmically. Every forceful thrust, every time I ground my groin against her flawless cheeks, she’d grunt and move her hand faster. Sweat dripped from my brow as I drove it into her fast and relentlessly. Her ass stayed ultra-tight on my cock and made slurping noises whenever I drew my rod out.

We were both panting and I felt that familiar tingling. I increased my efforts, spreading her cheeks further apart as I split her last virgin hole nice and wide. “Oh god, I’m gonna cum,” I hissed. She didn’t answer, just grunted with more urgency. I began touching the end of her young ass on every invasion, and she yelped.

Her guts squeezed the tip of my cock. I’d never felt anything like it, and my own cheeks tightened as I pressed as far as I could inside her hot hole. I pulled out one last time, then ripped into her again, harder and deeper than before. She cried out in pleasure and pain and my dick pulsed, coating her dirt tube with cum. I gave short thrusts, keeping my shaft at the end of her while each shot of cum sent shivers through me.

Finally, I was through, and I collapsed on top of her and we fell flat on the bed, my softening meat still in her clutching ass. She was cooing gently, the sides of her big tits pillowing out from her rib cage and heaving slightly. Her thick hair stuck to her sweaty neck and forehead, and I moved some stray strands from her cheek and gave it a kiss. “Thank you so much Lisa,” I whispered. “That was the most amazing sex I’ve ever had.”

“I’m glad,” she answered sincerely. “It felt good, actually. It felt sooo big. I’m glad it made you happy.” What a good girl, trying to make me happy. I melted.

We rested for a moment, then I let her up to use the bathroom. My dick slipped out and I looked at her abused hole. It was red and slightly opened, and my copious cum surrounded it, leaking out and sticking in her treasure trail of pubes that led from her anus to her pussy.

Wow. Unfortunately, we didn’t fuck much after that because of my loyalty to my college love. And my idiocy. (Of course, to be fair, the college girl was my best lay ever, truth be told, so I had no conceivable reason to cheat. For a time. More on that later).

Three years later we hooked up a few times, and she actually invited me to stick it in her pooper. Sadly, I was raging drunk and don’t remember much of it. Soon after that, she tired of being used as a late-night fallback and I was too stupid to be better to her. I often think of her now and wonder where she is and what happened to her. Is she still cute as hell? Did she get chubbier with age as most of us do? Does she still have a wonderfully tight ass and did she let others experience its joys?

To whomever ended up with her, I’m sure you’re a lucky guy. And you’ve got me to thank for those enormous jugs. Late in our relationship she told me she was considering a breast reduction, and I talked her out of it. You’re welcome. You could thank me by letting me have another go at her…

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