This past summer my family (Fiancé included) went to the Florida Keys. We had rented two rooms, both with dual queen beds. My Fiancé (M20) and I (F22) were in the room with my parents, while my Brother and his wife were in the other room. These rooms were directly next to each other, and a little door was the only separator.

It had been an exhausting few days in the Keys, walking/touring eight to ten miles every day since we had gotten there. Around the fifth day of our trip, Andy and I eventually decided to settle into the “bedroom” area after watching whatever boring cable was provided through the hotel. We wrapped ourselves in the soft blankets and spooned, getting our alarms and reminders set for the night before turning off the lights and putting our phones to charge.

For a little context of why this may have gotten so hot and heavy, Andy will typically only wear boxer-briefs to bed, while I prefer to wear a simple t-shirt and underwear.

I felt Andy’s arms wrap tightly around me and pull me by the waist into a very, very close spoon. I always love that feeling, because he is the perfect height so my form fits completely within his.

Once everyone is ready for bed the lights go out and my parents turn on their white noise machine they always love to use. So we are sitting under the blanket, my ass directly against his waist, both basically naked completely concealed by the covers. I can feel his hand drift along my torso, disregarding the t-shirt entirely and cupping my right breast. I sigh, a slight smirk forming on my face as I gently wiggle my ass against his crotch.

I lean my head back in a nuzzling fashion as Andy’s breathy voice fills my ear, “Want to get lucky tonight, my darling?” I can feel his breath run around my ear and down my neck as he nibbles on my earlobe.

I feel a shiver run down my spine at his words, and I can only bite my lip and whimper softly back to him, “Yes, please.”

I can hear him gently chuckle, his hands now moving to remove my underwear, my feet shuffling just slightly under the covers to kick them completely off. (I figured I wouldn’t want them back on anyways) His boxers quickly follow, his erection immediately pushing against the cheeks of my ass before I redirect it to my awaiting sex. I had been soaked for hours at this point, Andy had been teasing me all day while we toured around the Keys. Even going so far as to push me into an alleyway just to grope and make-out with me, I couldn’t have been hotter in that moment.

He slides easily into me, but moves agonizingly slowly, just to continue his teasing. I can almost feel him smirking in enjoyment behind me, taking in every small gasp and whimper I am making as he slowly reaches the bottom of his shaft, pulling my leg up just enough to allow himself even farther inside of my pussy. Now he is in, I can feel such a relief at having him buried into me… Then he begins moving, taking long, deep strokes, each one forcing me to relive that first teasing stroke as I am continually stretched by his girth. I can feel my pussy throbbing, my clit just barely being brushed by his balls every time he bottoms out into me. My hands are tightly holding the blankets, his are on my mouth and breast, keeping me quiet while tempting me to scream out his name in pleasure. I can feel his fingers rolling and pinching my nipples, so many years and it still amazes me how expertly he manipulates my body.

A single moan begins to unearth from deep inside of me, I’m so glad he was covering my mouth.

Andy pulls back for an especially long stroke, and I can’t wait to feel him go from the tip to completely within me, but his cock slips out of me. (I was practically gushing at this point, so I’m not surprised) I can feel his hips begin to move, but this time his cock pushes against my asshole… Most days I would have immediately redirected him, but tonight I really felt like having my ass penetrated. As Andy pulls himself back and tries to reposition, I put my hand back on top of his and take control of the tip of his cock. I align my hips to the correct spot and push the tip of his cock against my asshole again. I can feel him hesitate, but I quickly assure him by continuing to guide the head of his cock into me. (I’m so glad about the teasing he had done to me earlier, at this point.) I let myself rock against his dick, inching him into me slowly, allowing my ass to adjust to his girth. I can feel his balls push against my pussy and his breathing is fast against the back of my neck.

I’ve got his entire cock up my ass, and I couldn’t be happier about it. I just gently rotate my hips, letting his cock stretch me out over the course of a few minutes, my hands gripping his hips to keep him firmly in place. As I let go of his hips, I can feel his free hand move to mine, guiding me back and forth across his length with nothing but a nod from me.

I can feel his fingers curl against my hip bone, something that drives me absolutely insane, and his pace steadily increases as both of us start getting into this situation. I’m practically begging for it at this point, and he knows it. His pace, force, and ferocity increases; My need to moan increases as well, as I practically bite his hand to stop myself. It’s near impossible to hold my own body back, and I can feel myself building to something so different from every other time I’ve fucked Andy.

As I near my peak, Andy is pounding me as hard as he can without making the bed squeak and wake my sleeping parents just a mere 7 feet away from us. My body is completely reciprocating, my hips forcing the entirety of his cock into my ass with every stroke.

His voice one again fills my ear, a smooth, raspy tone he only gets when very tired or very, very horny, “How about I fill your ass tonight baby?” I am completely unable to speak, just nodding my head and pushing myself harder against him in response.

I want release, I want all of his cum, his cock stretching my ass made me feel so completely different but I was loving it. He slams himself into me, unable to contain his building orgasm as a torrent of cum begins to fill my ass. I can feel every twitch, and as he cums, so do I. My first true anal orgasm. While he can’t move, my body just wants this feeling to keep going, and it doesn’t stop for a single second, impaling myself on his thick cock over and over… I can feel multiple orgasms compiled upon one another, and I can feel his cock continuing to pump my ass full.

I feel my body begin to come down from this intense orgasm, pushing back and completely taking Andy’s still erect cock inside. My body starts to convulse from the pleasure, Andy just barely holding back a strangled cry from the bottom of my throat.

Before this night, I had only done anal a handful of times, and those sessions were less than pleasurable. I hadn’t been able to take much more than him just barely rocking inside of me. Needless to say, after that orgasmic night in the Keys, we certainly found an entire new world of fun to explore.