Late Night First Time Anal

I met Arriana when I was dating my high school sweetheart, Natalie. I would see her every 2 months or so as she was the best friend of my girlfriend's sister. We would see each other at parties or we would all go out to dinner or bar hopping together. We would always engage in good natured flirting, which always felt safe because we both knew there was no way we could ever do anything about it. Arriana was a "good Catholic girl," which in my experience means more work is initially required to convince them to be naughty, but once you do, it is so very worth it.

Arriana is a stunningly beautiful girl, one year older than I am, with long, dark brown hair, very tempting green eyes, and that kind of smile and laugh that while looking into her eyes talking to her, always made me want to grab her, pin her up against the wall and passionately press my lips against hers. She has that ball buster personality that some girls pull off just right with the perfect amount of wit, flirtiness and charm. I never knew whether I wanted to kiss her, or bend her over my knee and smack her sweet little ass with my big, strong hands. Her breasts are a smaller 34B, but very perky and responsive, and I was always curious to see if my theory that women with breasts smaller than a C cup are better in bed would apply with her. In my experience, women with DD cups don't work as hard because they think we'll be so distracted by their ample bosom that we won't bother to notice the effort that they put forth in bed. She had a flawless body and perfect complexion, due to her refusal to go in the sun. I was always attracted to her and was always happy to hear that we were going to be in a room together.

I also enjoyed Arriana's penchant for naughtiness along with her style. She was notorious for wearing trendy, sexy shoes, and she always wore nice clothes that were sexy but never slutty. Her pants always outlined her heart-shaped ass, with the slightest hint of extra padding, but she never came off as arrogant. When we were both 22, I had broken up with Natalie, and Arriana and I found ourselves in my parents' bed after a party I'd hosted when they were out of town. We had been flirting relentlessly with each other all night and this seemed like the perfect opportunity to finally reward ourselves for our years of pushing the envelope. I made more of a silly attempt to make out with her than a serious attempt to hook up. "We can't." she said. "You're my best friend's sister's ex-boyfriend."

"Well, you're my ex-girlfriend's Aunt's niece's second cousin's second cousin's sister's best friend, so I wouldn't make out with you anyway." We ended up laughing and enjoyed flirting and talking until the sun came up. One of the last things I remember saying before we passed out with our stomach's hurting from laughing so hard was "it doesn't count if we have butt sex."

Later that year, I had resumed having an on-again, off-again relationship with Natalie and we all found ourselves at a Halloween party. Natalie and I had done some pretty freaky things over our 6 years together. I had turned her into a bit of an anal freak from the first time I slid my finger into her ass while eating her delectable pussy. Over the years she picked out anal beads, butt plugs, and various sized dildos and vibrators. We'd had anal sex several times, but she mostly enjoyed having her ass pleasured with my tongue, with my fingers, or being double penetrated by me and a toy. Truth be told, she was rarely able to handle having my thick, 8.5 inch cock in her backdoor. It usually only worked when she was drunk, and even then I could only put it about halfway in.

While at the Halloween party, Natalie, Arriana, and I were playing pool together. Natalie and I were having one of our brief hiatuses but once the alcohol began lowering our inhibitions, we began talking pretty openly about some of our exploits and experiences. Arriana had heard us talking like this before, but she was noticeably equal parts surprised and aroused when we started talking about our numerous experiences with anal sex. Arriana had apparently never experienced this and had a lot of questions. Before we had that conversation, she had always been one of those girls who, while maybe being minimally intrigued by the idea of anal sex, always said stuff like "no way" or "exit only" or "ewwww" or "ouch" or "never" that in my experience a lot of women with either no experience or negative experiences with anal sex say.

"Doesn't it hurt?" Arriana asked.

"Not if the guy you're with knows what he's doing and uses a LOT of lube." Natalie replied.

Arriana looked at me and said "and you enjoy doing that to her?"

With a sheepish grin I shrugged, "of course. Have you seen Natalie's ass?"

Natalie shot me one of her notoriously naughty grins and turned around to shake her ass in my direction, making all of us laugh.

"Of course," Natalie said, "it would probably help if you could find a guy a little smaller than 'horse-cock' here."

Arriana had actually seen my penis more than once before as Natalie often encouraged me to whip it out in front of her sister and in front of several of her girlfriends and even some of her coworkers. One night she'd actually invited me over to a get together she was having with 6 of her female coworkers and had me strip for them. I didn't mind showing off and she loved (sometimes literally) rubbing her girlfriend's faces in the dick that she got punished by, usually more than once a day.

Despite the fact that she had seen it several times, I still caught Arriana sneaking a glance at my crotch before making eye contact with me, smiling and blushing. This entire conversation had made me swell with arousal and it was about to be Natalie's shot. As she lined up a long shot across the table, I unzipped the fly of my jeans and placed my erection in the pocket she was aiming at, causing her to stand up and shake her head, and elicited an audible gasp from Arriana.

"You're insane!" exclaimed Arriana.

"Get that monster out of my way." Natalie said, fighting back a smirk, and took her shot, missing wildly.

"Dick," she said.

"Which hole did you have in mind?" I replied.

My shot was next. Natalie bent over, placing her tight jeans covered amazing ass in the pocket I was aiming at. Unphased, I promptly sunk my shot with a lovely background view. I did the same in the side pocket, despite the fact she tried to distract me by flashing me her tits. I finally missed when she upped the ante by mooning me, sans panties and seeing her little asshole winking at me for the first time in several months made me want to throw her down on the table and fuck her right then and there.

"You two are too much", Arriana said. "So how often did you guys do it that way?"

"We probably only had actually anal sex about once every couple months, but he would slide his finger up my ass pretty much every time we had sex."

I nodded in agreement and added: "bless her heart, she would try, but she could never really take more than half of it, and only if she was pretty buzzed."

Arriana asked several more questions and by the time we were done, she definitely seemed intrigued by the idea of having a dick in her ass. I still believe that our conversation that night set the stage for what would later become one of the most memorable nights of my life.

We were both so worked up after our conversation and as the party was winding down Natalie said "want to follow me home to make sure I get there ok?" She tried her hardest to suppress the wicked grin behind her otherwise innocent question, but her intentions were exposed by the look in her stunning green eyes. I had heard several people over the years tell Natalie that she had kind of an "exotic look" and a few people had even asked her if she had any Asian ancestors. Albeit loosely based, she always kind of reminded me of Princess Jasmine from "Aladdin." Natalie is a petite and very athletic girl with long, dark brown hair and she impeccably supported my theory that women with smaller breasts are better in bed. At 5'2" with the most perfectly shaped 36B cups I've ever seen, in person or in pictures or movies, she was the very embodiment of that saying: "a lady in the streets and a freak in the sheets." She had run track in High School and, like Arriana, had the kind of ass you just had to turn your head to look at even if you were sitting next to your girlfriend. Being the chivalrous gentleman I am, I followed her home and we had the most mutually satisfying anal sex we had ever had together that night. She was able to take about ¾ of it and she came three times in about 15 minutes with me in her ass and her favorite vibrator against her clit. We were on-again and fucking like rabid bunnies for the next couple years.

As the years went on I transformed a little bit from a skinny and athletic 3 sport High School and collegiate athlete to building broader shoulders, and putting on quite a bit of muscle, making my chest and arms very toned. I could probably stand to lose about 20 pounds, but nobody else would be able to tell since I'm more than six-and-a-half feet tall. I am a handsome man, with short, dark, (with a little salt and pepper mixed in) hair and hazel eyes. My toned, muscular arms, my eyes, and my lips are my most complimented traits. While I have been told I am attractive, I have always believed that my sense of humor and my ability to exude confidence in any room of people have been the qualities that have attracted women to me most. I have a quality that always seems to put women at ease and makes them tell me their most guarded secrets and confide in me. This quality has also been successfully applied to sex, especially anal sex, as a woman being relaxed, comfortable and uninhibited is vital to a mutually pleasurable experience.

Natalie and I broke up about 2 years after the Halloween party and several years went by. Facebook became popular and Arriana and I reconnected. We were now in our mid-30's and she had gotten married and divorced in the years since I had last seen her. She'd had kids and hadn't lost the tiniest bit of her sex appeal. If anything, she was even more alluring than I'd remembered her. She now ran regularly and her legs and ass were absolute works of art, muscular and toned. She also now had a very attractive confidence that comes with age, having life experiences, knowing what you want, and not settling for less. I had been in a relationship with a new girlfriend for the last 2 years and had never cheated on her, and had never planned on cheating.

There was always something about Arriana, though, and I found myself inescapably drawn to her. As we spoke over messenger and exchanged numbers and began texting each other, our conversations quickly became inappropriate. I asked her if she remembered that conversation we'd had with Natalie all those Halloween nights ago and she said "yes". I asked her if she'd ever ended up trying it and she essentially conceded that she'd tried it, but I got the impression it had been an underwhelming experience. This experience had probably been with her stupid ex-husband who likely tried the "oops" method (trying to slide it in the wrong hole "by accident" with no preparation and no lube and then trying to play it off as a mistake). She sent me pictures of herself, one in particular taken up her very professional work skirt with no panties on while she sat at her desk. I remember that driving me wild all day knowing that every guy at her work was only one well-timed glance away from seeing her pretty little shaved pussy. I sent her a picture of my cock at about half mast and she replied with the wide-eyed emoji:

"Oh my God it's been so long since I've seen it! I forgot what it looks like hard."

"I would be glad to show you to refresh your memory, but I would rather just show you in person."

We worked each other into an absolute frenzy with our sexts and pictures over the coming months and I finally told her that the next time I was back visiting near where we grew up, I was going to come to see her. I wasn't quite sure how she would respond to actually crossing this line from fantasy to reality, but I was pretty confident that she wanted to experience all of the things I had told her I wanted to do to her.

As an admittedly slightly flawed (and in hindsight, brilliant) justification to be in a bed with her with our clothes off as a man in a relationship, I told her that I would only be able to do oral, and that if she behaved herself and came all over my face like a good girl, I would "let her" take me in her ass. She laughed but she knew I was serious. Much to my pleasant surprise and delight, she agreed without hesitation, though she said: "I'll try. But I really don't think that monster of yours is going to fit."

I don't know if Arriana thought I was bluffing, and I don't know if she was bluffing, but over the next couple of weeks, we became absolutely insatiable and couldn't wait to see each other. I planned a trip "home" to my hometown in early November, and we set about trying to coordinate what would be the best day and time to meet up. Because her license had been suspended, she couldn't drive, so I would need to make the 2 ½ hour drive North to her house. My best friend is the type who is difficult to get away from when visiting, and I knew there wasn't going to be a good opportunity to sneak off at a reasonable hour. Arriana and I agreed that I would hang out with my friend and then try leave around 10:30. She would go to sleep and give me the alarm code so I could let myself in and wake her up in whatever way I wanted when I got there. My best friend and I generally drink enough when we're together to knock out a stable full of horses, but I held back a bit and smoked quite a bit of weed with him. I planted the seed that I would have to get going around 10:00 and I actually managed to leave by about 10:45.

I began making my way up to Vermont and for the entire ride I daydreamed about what I was going to do to her when I got there. I remember wondering if she was really going to go through with it or if she was all talk. I knew she wouldn't have had me drive 2.5 hours for nothing to happen, but I was only about half sure that we were actually going to have full on butt sex. Truth be told, I hadn't even completely convinced myself that I would be able to do it myself so I figured I would stop worrying about it and just let whatever was going to happen, happen naturally. I was also daydreaming about what she must have been thinking. I was thinking about how horny she must have been when she went to sleep and loved knowing that the last thing she was thinking when she fell asleep was: "oh my God, I'm going to get woken up in the middle of the night and get my virgin ass fucked by a guy I've never even kissed before."

My heart was racing by the time I got off her exit and I easily found her house and parked my car in her garage as instructed, so as not be seen by her stalker ex-husband. Her bedroom was on the second floor at the end of the hall and I quietly made my way up the stairs. She lived in a house that looked almost exactly like the house I grew up in, and even the same stairs creaked. She had lit some candles so that I would be able to find my way to her room and my heart was still racing as I walked slowly and softly down the hallway. She had asked me what she should wear to bed and I told her I wanted her to be wearing only those panties that cover about half of a woman's ass cheeks and nothing on top. I slowly opened her door and she had lit some candles in her room and was sleeping peacefully under a very warm and comfortable looking white down comforter. It was slightly cool in her room, and the candles made her room smell like a mixture of a rainstorm, and clean cotton.

I paused to look at her admittedly beautiful face before I slowly peeled the comforter off of her, and felt like a kid unwrapping his most coveted big ticket Christmas gift. She was laying on her stomach and I pulled the covers down low enough to sneak a peek at her exquisite ass. I began planting kisses on the small of her back and running my lips and my tongue slowly up her back to the back of her neck. She felt so warm and soft against my lips. She was already stirring and I knew she was awake when she began moaning in response to my mouth exploring her almost impossibly soft and very responsive skin. I kissed her ass cheeks and lightly bit her right cheek, eliciting the sexiest little giggle from her before resuming my oral exploration. I knew already that I was going to be taking my time with her and savoring every second of this experience.

I removed my own clothes, leaving just my boxer briefs on while turning her over and we finally made eye contact and spoke. She absolutely melted me with the look of unbridled lust, naughtiness, flirtation and affection in her gorgeous green eyes and smile. I couldn't believe it had been so long since I'd seen her and how little she'd changed. I couldn't believe that we had never even kissed before and I had somehow charmed my way not only into her panties, but that I was about to charm my way into her most heavily guarded of orifices. "Hi" she said in the most adorable and innocent way. I smiled, returned her greeting as I laid on top of her and pressed my lips against hers. I immediately felt that current that runs through your entire body when you kiss someone with whom you have undeniable chemistry, and who knows exactly what she's doing with her lips. Her kiss was a microcosm of what was to come, her lips parting in an almost submissive way to allow me to kiss her deeply, our tongues dancing and intermingling together. I couldn't get enough of making out with her and we rolled onto our sides, facing each other. My big, strong hand made its way down the small of her back to her butt, and I began squeezing and manhandling her firm cheeks, somehow even softer than the areas I had already explored. I again lowered my lips to her body, kissing her stomach and working my way lower, lifting and spreading both of her legs so I could kiss, lick and lightly suck on her thighs and the backs of her knees. I planted soft kisses on either side of her panties and lightly kissed her lips through her panties, causing the fabric to press against her crotch and I felt that she was already soaking wet in anticipation of what I was doing and what she knew I was going to do to her.

I worked my mouth back up toward her neck, stopping to run my tongue slowly around, but not touching her nipples. They began to harden and she began arching her back, trying to get her nipples to touch my tongue, but I refused to give in. I hovered my tongue over her left nipple, just enough to allow some saliva to run down onto and coat her tit. I then lifted my head about 8 inches off of her chest and lightly blew cold air onto her chest. Her tantalizingly responsive nipple hardened to the point that it looked like it had to have been aching. Pointing straight up in the air, begging to be touched, I again resumed my teasing, finally forcing an utterance of "I'm going to kill you."

After blowing on her fully erect tit one more time, I closed my lips around her nipple and began lightly sucking while swirling my tongue all around her areola. She threw her head back and arched her back up towards my mouth, finally giving her what her body had been begging for. I closed my teeth lightly around her nipples and slowly moved my face up to her neck, kissing, licking and sucking her in places that repeatedly made her moan and arch her back. I pinched her sensitive nipples between my thumbs and index fingers, still slippery with my saliva as my mouth continued to explore her neck and her ears.

I knelt on the floor, pulling her to the edge of the bed and pushed her legs straight up in the air, pulling her panties slowly off, getting my first glimpse of her very attractive, downright edible looking pussy. The only hair to be seen was a short landing strip and her lips were already swollen and glistening with her precum. I removed her panties from around her ankles as I pushed her knees back, putting my hands on the backs of her knees. I planted light kisses against her lips, and lightly sucked her labia into my mouth. I kissed her where her barely visible pubic hair was, just above her clit, causing her to try to gyrate her crotch against my face. I slid my face down, and planted one more kiss with slightly more pressure just against the opening to her pussy before pushing her knees back, automatically making her cheeks spread apart. I slid my tongue between her cheeks and began to rim my tongue around her puckered ring. Her gyrations ceased, clearly curious about this new sensation, but not quite sure about what I was doing. I finally pressed my tongue against and began massaging her asshole, lightly pressing against her sensitive opening, allowing just the tip to slide inside. Her moans were mind-blowingly hot. It is such a vulnerable position for a woman to be in and I loved the sheer naughtiness of her enjoying me eating her ass.