Anal In London

For those of you who don't know me, suffice to say that I'm a typical south Florida mom. Like most south Florida moms I'm not originally from Florida, but from a colder more northern part of the US, I have a workaholic husband with a job in finance, and a social calendar that revolves around other moms like me. I'm very white, but always at least baseline tanned, I have light brunette hair, blue eyes, and the body of a woman who does yoga, swimming, and the gym every day of the week. I'm also quite short, about 5'2" but despite my petite size, I do wear 34DD. Life for me at age 35 is mostly ferrying the kids to school and extracurriculars, gossiping with other wives like me, and fucking my husband whenever he happens to be around. His work sends him all over the world, sometimes for months at a time, so my routines become fairly cemented, and, well, I cheat.

I've been cheating for several years now. Sometimes with one person for a bit, but those never last too long, its mostly one offs or one weekend, or one week, etc. I sometimes cheat with men that I meet while traveling, sometimes I cheat with men I know from my social circle, but the overwhelming majority of the time, I cheat with men who are much older than me and married. I don't know exactly why I find much older men so attractive, but I've speculated that its because they are the opposite of my husband, who is younger than me, very athletic, and aggressive. Older men also tend not to be within my regular routine life, so its always convenient for keeping things secret.

The dynamic of sex with older men has always fascinated me, and it brings a very particular sort of energy to the encounter that I cannot find anywhere else. There simply is no way to describe the sort of excitement I get when I'm pinned under an old man's big belly, with his cock exploring my pussy, and his tongue exploring my mouth. Over the years I've had the opportunity to indulge this preference many times, enjoying older men from different cities and countries, as well as husbands, fathers, and other relatives of women in my social circle. Cheating has given me a unique way to connect and communicate with people, to know things about them that they may not even know about themselves. This is part of the experience for me, learning what someone's true face is, their real nature.

Today's story comes from about a year ago, well into my cheating career.

I was tagging along with my husband while he did some work in London. We visit London fairly regularly, since his bankers are all from there. He runs off during the day to various offices and meetings, and I fill the time reading, shopping, and lounging about at the hotel. Business dinners with his banking partners and their wives usually fill the evenings, and the perfect tedium of people who don't want to be there but have to for work settles into the conversation.

On one of those evenings, my husband decides to accompany his partners to a cigar lounge after dinner, which I know means he won't be home until quite late. Having just been bored to tears by the table conversation I give him my blessing and decide I'm going to read a book with champagne in the bathtub of our hotel suite. I'm a little frustrated since I did get all dressed up rather sexy, wearing a body tight red cocktail dress, low cut, and low back. As I'm walking back towards the elevators, I decide that this cocktail dress deserves a cocktail, and I sit at the hotel bar. Its nice in a sort of art deco way, gold plated, high ceilings, a sort of homage to the roaring twenties era. The bartender is a sharply dressed young man with tattoos on his arms all the way up to his hands. He smiles at me while sliding me an old fashioned. I take my first sip and have my first look around.

Theres not many people in this evening, just two couples far away by the windows at an empty lowball glass at the end of the bar. The glass's owner returns from the bathroom and I get my first look at my lover for the evening. The first thing I notice about him is how tall he is. Hes noticeably taller than my 6'3" husband, and has long hands and arms that accentuate his height. His skin is almost gray colored, and on his lanky body makes him seem a bit gaunt. Hes clean shaven and has a his hair in a sort of marine core high and tight cut.

He notices me processing how tall he is and starts our evening with: "well, you seem to be the perfect size" in a leathery British accent.

Now I've heard just about every short joke you can think of, but still in shock from his skinny tall appearance, I take the bait and ask "perfect size for what?"

He calmly walks over and places his empty whiskey glass on my head, "to be my drink holder," as a grin appears on his lips, "what did you think I meant my dear?"

The conversation and cocktails that followed revealed to me that this man was from northern England, was widowed, and has two sons older than me. His eyes peered at me from an almost sunken position from inside his head, he was so deathly skinny. He laughed at my attempts to describe London as an American, and his long fingers slowly found their way onto my arm from time to time. After a while his smile disappeared and he looked at me with a sort of piercing seriousness, rested his hand on my thigh, and asked if I would like to go up to his room. Up until that point, I wasn't particularly horny, but something about the sternness of his face, the large hand on my little thigh, and the knowledge that he knew I knew what he meant, give me that delightful little shiver of fear that gets me starting to feel slippery between my lips. I just nodded my agreement and he lead the way to the elevators in silence.

It was probably a little after 10:00pm when we stepped into his room. It wasn't a suite but the hotel is generally nice so it had a little sofa in it that he ushered me to. He wasted no time planting a long kiss on my mouth, his whiskey and my champagne punctuating each repeated press of our lips. His large hands flowed over my body, thinly protected by my cocktail dress, with a relish that let me know he'd been thinking about how he would do it all evening. I felt especially small being handled by him, and combined with the fact that he was in his late 70s got my pussy pretty much entirely ready. His fingers slipped under my dress and felt for my warmth and wetness, but he stopped kissing me once he found it.

"Ohhh no panties on tonight? Naughty girl," a wicked smile crossed his face and before I could offer some sort of defense he had taken one of his large fingers, slickened it with my wetness, and started massaging my asshole. I gave him a look that made him comment "I know what naughty girls like."

He was right.

The feeling of his knuckle pressing my button and his finger circling my asshole got me feeling very red and ready to cum, but I didn't cum until he pulled my tits out of my dress and started licking and sucking them. I came as politely as I could, but I still cried out a bit, trying to stifle the sensitivity that always follows. That was his signal. He stood up and stood me up by picking me up under my arms, like a doll, then he unzipped my dress and watched as I used my thumbs to slip it over my hips onto the floor. Then he stepped backward and disrobed faster than I have ever seen a man do before. It was like his clothing just fell off of his frame, which was now nude in front of me, in all its lanky tallness.

I was sort of expecting that he would have a big cock, just because of how tall he was. I know that's not necessarily how it works, but I didn't try to rationalize this expectation while flirting downstairs. I now was presented with one of the largest cocks I've ever seen, which after cheating for a while, was saying something. I am no size queen, I have never been one, and being small I find bigger cocks are a bit of a challenge to deal with comfortably.

This was going to be quite a challenge.

He walked it over to me and I almost didn't need to kneel to start sucking it. It was like a can of tennis balls, thick and hard, with a sort of knob on the end, I couldn't touch my finger and thumb together when I gripped it in my hands. I had my knees in my dress on the floor, and his cock in my mouth. Every now and then I picked up his cock and gave my mouth a break to lick and suck his balls, which hung lower than they probably should have, and mercifully were not as abnormally large as his cock. He told me to look up at him while I sucked it, and I obeyed, meeting his steely stern gaze with my baby blues. I put my hands on his hips and pulled his cock into my mouth, not breaking eye contact, but making sure he watched what I did. I couldn't take much more than a little past the head, but once it got into the back of my mouth, I started trying to swallow it, squeezing him with my throat. I realized my husband taught me to do that, which I was now using to please an old man I'd just met. He didn't moan, but his breathing sped up, and I could feel his legs starting to tighten. I knew that cum would be shot into my throat if I proceeded, and I sped up with the secret hope of escaping this encounter without having to fuck his huge cock, but he pulled me to my feet and tossed me onto the bed, and I knew I was in for quite the night.

He pulled me to the edge of the bed while he remained standing, I laid out flat on my back with my legs open; I put my feet on his abdomen. He still had to hunch over a bit to bring his cock to my pussy, and he steadied himself by grasping on to one of my breasts while he positioned his giant cock at my opening. I saw my tiny little shaved pussy, with its cute little closed lips, being approached by his huge dick, and the prospect of fitting it in felt absurd, but he slowly rubbed the head up and down, slow poking in and out gently, cautiously, and with each little approach, my pussy accepted a little more and a little more. I was able to control how much he put in a little bit with my feet against him, but he just took my pressing as an invitation to lick my toes which he did. I don't know why people like doing that, but he did. He wasn't wearing a condom, but I wasn't sure if there was one for him. Once his head was fully inside me, I started to get that feeling of complete fullness, and I felt his uncircumsized cock brushing against my inside button.

I felt the beginnings of an orgasm approaching and I started breathing heavier, trying not to squeeze him too hard as not to wear out my pussy, but once he reached the back of me the orgasm hit all at once. I grabbed on to his arms and dug into them with my fingers as I rode the orgasm out, I let out a few small cries and felt the pleasure rippling through me, and I finally relented and allowed my pussy to squeeze his cock unrestrained. Again he didn't moan, just his breathing got heavy and a look of concern crossed his face, I thought he would cum, but once my orgasm was over, I saw that he was still hard, still standing, and only had about half of his length inside me.

He slowly backed out and went to his knees at the edge of the bed, my pussy felt real relief and started to recover. He picked up my legs under my knees with each hand and moved me so he got a clear view of my asshole, which he started to kiss and lick. The feeling of his tongue probing my asshole got me back to full horniness. This man licked in circles, big long asshole to clit licks, and even began rubbing his thumb around it. I was a few more circles away from an orgasm when he stood up again.

I wasn't entirely ready for what happened next but he gathered some of the cream from my pussy that was still on his cock, and put it on the tip of his dick. I figured between that and the saliva he'd left on my asshole he meant to fuck me in the ass. I love anal, but I was certainly not sure how this was going to work. He draped my legs over his forearms and gripped me along my sides. The fact that I was now fully within his control made me horny to try him in my ass. He again slowly prodded his huge cock against my well licked asshole. I was certain that this wasn't going to work, but then I felt my asshole loosening with each approach, and the fact that he was essentially pulling me onto his dick made me quite ready to try. With each millimeter that I opened up more of his dick pushed into my asshole, until his head was fully in, where he gave me a minute to adjust to his size.

He didn't waste this minute as he kissed me again and took a suck at my tits, keeping his same serious look. I wanted to whisper "fuck me" to him, but he sensed it before I could get the words out. He began the first real fucking of the night, slowly building speed as it was clearer and clearer that we had reached the comfort stage. Any girl who knows anal, knows there's a moment when you're fully relaxed and can take the pounding you're about to receive.

I began taking it.

He managed to get a bit more of himself in my ass than he was able to in my pussy, his long hanging balls frantically spanking my asscheeks as he fucked me. I started to feel the beginnings of an anal orgasm, the stern look this old man was giving me while he shoved his thumb in my mouth and his cock in my ass was setting the process in motion. I didn't hold back at all this time and cried out loudly as I felt the orgasm rolling through me, I clenched my asshole tightly as I came. The clenching set his own orgasm in motion as I felt him tense up, and within a few more pumps, he spilled his warm cum deep in my ass.

Afterward he slipped out of me, he went to the bathroom, and I lay there to recover. I remember kissing him one more time as I walked my cum filled ass back to the elevators and up to my suite. I took that bath I wanted, but lacked the coordination for a book or champagne. My husband didn't get home until late, and by then I was already half asleep, exhausted by what had happened. I didn't run into that man at any point later, but I was glad I didn't since I would not likely have been able to repeat that performance another night in a row.