Carla Jean, never married, was the type who loved to play around, flirting with men but never taking them too seriously. She generally lived life as if she were on a playground. My sexual fantasies about her always intensified whenever there was a family event.
I particularly remember a beach vacation that had me hiding in a back room of the beach condo almost on a daily basis. Excusing myself to take a shower to “get cleaned up” after a day at the beach, I found myself in a locked bedroom of the condo, lying back on the bed naked, stroking my cock as slowly as I could manage. As I pumped my cock, I pictured Carla in her bikini, putting on a show for every young stud who came within fifty yards of her.
Her long brunette hair flowed around her shoulders, her amazing tits and ass were perfectly displayed by the skimpy suit she wore, and she had a smile that dazzled every guy who saw her. She had all the college boys busy trying to hide their hard-ons from their own jealous girlfriends.
Every masturbatory session I had ended with me lifting my ass up off the bed, pumping my cock frantically, and shooting a thick stream of cum straight up onto my chest. All the while, I was imagining that Carla had taken off that bikini and fucked me to a raging orgasm, or let me shoot my cum all over her perfect breasts. I pictured my cum dripping from her hard nipples, or her sweet hot mouth deepthroating my cock and sucking my balls dry.
So, Carla had been at the center of my fantasy life since I first met her; since I never talked about this with my wife, and certainly not Carla, I assumed they were both unaware of my “problem”. I intended to go on this way indefinitely, solving my problem at every family gathering by amusing my wife with my unexplained but appreciated increase in feverish sexual activity with her (coupled with an excess of private masturbation after every social occasion with Carla). All of that ended last night, and I don’t know what today will bring. My cock is already hard just thinking about it.
This past week, the whole extended family gathered for a big wedding celebration which was to last several days. The first night, all the women of the family were going out on a “girls night out”. After the four-hour plane trip, I was tired and planned on just relaxing in our hotel alone. As usual on these type of big family events, my wife and I shared a two-bedroom suite with Carla. The two sisters enjoyed spending time together at the hotel, but naturally it made my fantasy daydreams that much more frequent (I never complained).
My wife got ready and took off for the evening. She wouldn’t be back for hours, but she told me that Carla had gone back to her own room and was sleeping off a bad headache. My wife reminded me to be quiet and let Carla sleep; I told her I’d find a game to watch, relaxing on the sofa in the suite’s living room area, and wait up for her.
My wife kissed me goodnight, laughing at me and saying she knew I’d probably just fall asleep on the couch. She left and I soon found something on TV, turned out all the lights in the room, and turned off the TV and fell asleep in thirty minutes just as my wife had predicted.
Not long after, I sensed some movement and woke up; I was totally alone in the part of the suite that was a living room connected to a kitchen area. I had fallen asleep after kicking off my jeans, wearing nothing else but boxers and a t-shirt. The movement I had sensed was Carla Jean, tiptoeing through the darkness toward the kitchen. She opened the fridge to look for something to drink.
I don’t know how I kept my presence hidden, I felt like yelling out “holy fuck!” By the light of the fridge, I saw the most amazingly erotic vision; I couldn’t have imagined anything more incredibly gorgeous and sexy in my own fantasy daydreams while getting off.
Carla Jean, unknown to me, apparently always wore sexy nighties in bed, even when traveling alone or while visiting family. As she bent over to search the fridge, I stared at her lovely naked body, clearly outlined beneath the sheer fabric of her low-cut baby doll.
The thin straps barely held the nightie onto her bare shoulders, and it wasn’t even long enough to cover her beautifully firm ass. As she leaned down to grab a bottle of wine, the back of it slid up, uncovering her bare cheeks – no panties! I could see those perfectly formed 38C tits, swinging slightly as she dug around in the fridge; goddamn, she looked so fucking perfect!
As the cold air her caressed her (along with my dirty thoughts), I could plainly see her nipples get hard and jut out a good half inch. Her tits strained against the tight-fitting top, the twin points of her nipples creating hard little points in the fabric. The cool air wafted across her pussy and up across her body; how I managed to stay quiet, I’ll never know.
She turned away from me, flipping on a dim light in the kitchen. There was just enough light to see that her naughty outfit was a sheer yellow color, a perfect contrast to her lovely deep tan. She had no tan lines at all; she must have been doing a lot of nude sunbathing lately. She poured herself a glass of wine and turned around, only to find me staring at her like a dumbstruck high school kid seeing his first naked picture.
For as long as I live, I will always remember that I was speechless, but Carla Jean took it absolutely in stride and didn’t even act surprised.
She just said, “Oh hi, Bill! I assumed you were asleep in the other bedroom; sorry if I disturbed you.”
My heart began pounding as she walked over to the sofa and sat beside me. I tried so hard to make eye contact, but those long tanned legs, barely concealed pussy and gorgeous tan tits made it so fucking difficult. The fact that I was only half-dressed myself, wearing just boxers and a shirt, only made it worse.
Carla Jean knew exactly what she was doing to me, and she loved the teasing; she didn’t seem to care about how difficult it was for me. She and I tried to ignore how we were dressed. We both made ridiculous small talk about the impending wedding, etc.
Finally, she had finished sipping on her wine glass and said to me, “I think I’ll have another, do you want one too?”
I said yes, just so I could watch her walk away from me, back to the kitchen. Her beautiful ass swung back and forth like a supermodel on a runway, and she turned and smiled back at me as she poured the wine. I was transfixed by the carefree way she put herself on display for me to enjoy.
I was completely focused on her and didn’t even realize that my cock had pushed itself out below the bottom of the leg of my boxers. My shorts were hiked up a little and the entire head of my cock, still not fully hard, was exposed to her view as she came back out with our drinks. She saw my swelling cock head and smiled to herself, but said nothing.
We both took a drink of wine, and in the ensuing lull in the conversation, Carla simply said, “Bill, I don’t know if this is a good idea or not, but I’m just gonna do it because I think I’ll like it.”
She leaned forward and kissed me, lingering just long enough to make my cock jump and let me know it was not a sisterly kiss. She laughed and raised her glass, making a toast to a fun-filled weekend, and we each took another drink. I gulped mine down, and Carla leaned forward, lips half-parted, for another kiss.
This time our kiss was much longer, wetter, and more passionate. Her wet lips massaged mine, and she had held a little taste of wine in her mouth, letting it flow into my mouth as her tongue teased mine.
We kept kissing until we forgot about the wine glasses we both held. I accidently spilled a little on her neck and she dropped some straight into my lap. For a second, that brought me back to my senses; I started to get up, saying I’d get something to clean up the spill.
“No, Bill – no!” her insistent tone made me sit right back down. ”That wine is much too delicious to mop up; we’ll need to drink it!”
My head was spinning as I began to understand what she meant. She smiled at me invitingly; the splash of wine against her beautiful throat was running down into her cleavage and running down her tummy toward her pussy.
I looked down and noticed for the first time that her pussy was unshaven but closely trimmed; her lovely tight bush was soaking up the trickle of wine that ran from her chin down to her pussy.
We both put down our glasses, and she looked at my boxers. She smiled at the protruding head of my cock and saw that a big puddle of wine had soaked through the fabric. I could feel the sticky liquid running down onto my balls, as my cock hardened even more and poked out from the leg of my shorts a good 2 inches.
Carla Jean took my wine glass, set both glasses down on the table, and leaned back onto the sofa pillows. All she said was, “Like I said, let’s drink every drop; you go first!”
Oh my god! I was trembling, but I obeyed every word. She gave me instructions, telling me when to kiss, when to lick, when to suck. She moaned her approval as my hungry mouth cleaned up the wine spilled on her throat and shoulders. I licked up everything I could reach without taking off her clothes.
My hands were running up and down her sides, gently caressing her breasts but not touching her nipples. Her moaning grew louder and I knew exactly what to do next. I pulled her toward me and kissed her passionately, letting her taste the wine I had sucked off her lovely brown skin.
My hands roamed down her back, stopping for a minute to caress her naked ass as she moaned passionately and thrust her tongue into my mouth. I grabbed the bottom of her nightie and pulled straight up, whipping it over her head, her naked tits bouncing and jutting toward my face.
I leaned forward and began to suck hungrily. Those half-inch nipples were a dream, tasting of sweet spilled wine, and Carla grabbed the back of my neck and held on tightly as I caressed one fabulous breast, then the other. The stickiness of the wine was replaced by the wetness of my saliva, coating each nipple. I teased one wet shiny nipple with my finger as I sucked hungrily on the other, going back and forth.
I soon realized Carla had been fingering her pussy as I worshiped her amazing tits. Soon her finger fucking became more frantic, and the amazing dusky aroma of her oozing pussy juice began to fill the air between us. Beads of sweat ran down my chest beneath my shirt, and her tits were covered in her sweat and the wetness of my eager mouth.
Suddenly she pulled her fingers out of her pussy and gave me a taste. It was the sweetest womanly nectar I’ve ever experienced. I cleaned the pussy juice off her fingers, sucking, licking, and slurping noisily.
I let go of her body and she instinctively reached up to caress her own breasts. She began squirming as her pussy ached for more attention. She was eagerly pulling, pinching, and twirling both nipples; she then fell back onto the pillows, offering me her pussy.
I kissed my way down her tummy, which quivered as waves of pleasure raced through her tits and pussy. She was squirming, her pussy aching for something to replace the fingers that had been fucking it. I slurped at the spilled wine on her flat belly. Carla giggled a little as I swirled my tongue around in her belly button and then sucked on her pussy mound, enjoying the taste of her lovely triangle-shaped bush that was soaked and sticky from the wine.
Suddenly she groaned and arched her back and thrust her hips upward; she wanted her cunt sucked on, and she said so in so many words! I obeyed instantly; I looked up and saw her, head back, eyes closed, hands squeezing her tits and pulling on those nipples.
Goddamn, I swear those rock-hard nipples must have been an inch long now! I pushed her thighs apart, forcing her to spread wide open for me, and then slid the palms of both my hands under her ass cheeks. Her ass was quivering as she strained to hold herself up to my mouth. I gave her just a bit of teasing, kissing her pussy hair and the insides of both of her thighs, which were both shaking now too.
Then, suddenly, I gripped her ass firmly, my strong fingers digging into her flesh just enough to make her jump in surprise. I looked up and saw her eyes open wide and looking down to see me dive into her wetness. Her pussy was literally gushing a thick creamy liquid now.
The wine was all gone, but her pussy cream was even sweeter; I licked up and down the folds of her lips, and Carla grabbed the back of my neck and pulled me in tighter, humping my face as I lifted her entire lower body off the sofa and up to my eager mouth. She held on tight to my neck and ran her hands across my broad shoulders, my muscles straining as I lifted her up even higher.
Carla’s long tan legs flew open wide and she started flexing her incredible ass muscles beneath my hands.
”Fuck me!” she screamed. “Fuck me hard, goddammit!”
Her heels dug into my back; she was holding herself up now, slamming her hips up into my face as she held on to my arms. We were both shaking from passion and near exhaustion. My hands now freed, I began to swirl the tip of my tongue around her clit furiously as I pushed a finger deep into her pussy.
I kept thrusting my finger into her cunt, then two fingers, then three. I was massaging the inner walls of her pussy as my tongue attacked her clit.
“Now, Bill, now, now! Oh, fuck, oh fuck! Fuuuck!”
I sucked her enormous swollen clit, hard and long, protruding just like her nipples. Her entire pussy mound was covered by my wet mouth. I was drooling all over her cunt like a madman. Soon I had managed to suck her clit all the way inside my mouth and I attacked it with my tongue.
My tongue alternated between swirling and batting at her engorged clit; I began slapping at it with my muscular tongue. I pulled my fingers out of her pussy, then shoved two back into her quivering cunt as the third finger slid between her ass cheeks and up into her tight asshole. As soon as my finger entered her ass, Carla completely lost control of herself.
She began screaming over and over, “Oh god…oh fuck! Oh fuck, yes, yes, yesss!”
I’m sure her orgasm was heard up and down the hall of the hotel; I looked up to see her face thrown back in ecstasy. Sweat poured down her neck, and her tits were covered in beads of sweat. Her arms held on to my shoulders for dear life, her legs quivering and straining as she convulsed in pleasure, slamming her hot steamy pussy against my face.
I sucked and sucked hungrily at her quivering mound, alternating between sucking at her clit and tongue fucking her deeply. As she started her two-minute orgasm, I pulled my fingers out so I could gulp at her gushing wetness. My thumbs forced her ass cheeks apart and I let her pussy juice, along with the drooling wetness from my mouth, run down in a warm stream into her asshole.
I began probing both her…
