In my mind this started at a wedding. Two of my friends from high school were getting married and had a big outdoor wedding. That meant that everyone was going to be there and the party was going to be insane — which it absolutely was. One of the highlights was late that night after 95% of the guests had left and just the wedding party and a few really close friends / stragglers stayed behind. There was a lot of flirting and general sexual tension between just about everyone. We were in our early 20s, most of us drunk, and all having known each other when we were awkward kids seeing each other for the first time in ages in the heat of our respective “glow-ups.”
One of the friends that remained, lets call her Penny, was someone I had been off-and-on friends with for years. She had moved away at some point and we had lost touch. She was really good friends with the groom though — he had the biggest crush on her throughout high school and… well, still did to that day — despite that he had just gotten married. She was really cute, 5’5”, curly dark hair, big blue eyes, genuine smile, and lovable personality. In high school she had been incredibly skinny with a firm backside and small breasts. In the years that followed she had put on some weight but in all the right places. He B cups had filled out to Cs and her hips were a little wider and very inviting.
Sitting around the fire that night we all joked around and told old stories and tried to show off for one another. Penny’s boob size increase was a main topic of conversation as they kept nearly slipping out of her too-small shirt. Someone made a joke at my expense about my “big mouth” and I turned that around to let them know my mouth was big and very skilled. I even suggested that I could open it so wide that I could fit a tennis ball in there — I proceeded to open my mouth as wide as I could. No one believed me — which is fair, because it probably wasn’t true — and I continued on and said that I could fit one of Penny’s entire breasts in my mouth. They didn’t believe me, which is fair, because I couldn’t.
Penny did let me try though. She whipped out her tits and said “prove it!” I smiled, crawled over to her, and began to suck on her nipple. I could feel it harden in my mouth. I then slowly began to take as much of her breast into my mouth as I could while everyone around the campfire watched, laughed, or encouraged me on. I continued to flick at her nipple with my tongue, but no matter how hard I tried I couldn’t get the whole tit into my mouth. The group made fun of me for failing, but as far as I was concerned I had won. Nothing else came of it that night, I was doing a “one year abstinence challenge” so that was that. I never thought anything would come of it, just a goofy “me being me” over-the-top-bold joke. Well I was wrong.
A few months later I got a phone call from Penny on a random Wednesday night. “Do you want to go to Mardi Gras with me?” she asked excitedly.
“What? Like to New Orleans?”
“Yes! I’m planning the trip now and seeing who wants to go!”
“Uhm, well, uh, fuck it. Yeah. Why not?”
“Yeah! Really? Awesome! I’ll email you the details.”
My roommate, a friend from high school, walked by and asked what that had been about. I told him I was going to Mardis Gras with Penny and some of her friends.
“You’re going to fuck her.” He said matter-of-factly.
“No, no way. She has a boyfriend.” I replied.
“Yeah, that doesn’t matter. You’re going to fuck her.”
“Nah, I’m not into her like that.”
“You’re going to fuck her. Guaranteed.”
“You think?” I asked one last time. He nodded his head definitively and walked away singing “He’s going to fuck Penny. He’s going to fuck Penny.”
Fast forward a few months and the trip rolled-up on us. I had gotten my time off request approved, booked my flights, packed my bags, and bought a brand new digital camera for documenting the experience. I was told that in years-past the group that she went with was pretty significant; 5 – 10 of her friends all set to party for seven days in a rental right off of Burbon St. This year, it was only three of us. Penny; her brother, we will call him Richard; and me. That meant the cost of the hotel went up, but the freedom to do what we wanted was also significantly increased.
I met the siblings at the airport, we flew down to Nawlins, and the fun began right away. For those of you that have never had the experience of going to Mardi Gras I highly recommend doing it at least once — assuming the world returns to normal post-pandemic. It is a wild, alcohol fueled, hormone thumping adventure. Our trip mostly involved walking through throngs of random screaming people, stopping to get some new alcoholic beverage any time our current drink ran out, and taking photos of nude people on balconies or walking around the street. Penny was constantly flashing her tits to anyone who made eye contact with her and her brother and I earned our own fair share of beads with various flashes of our own.
The real fun began at whatever time it is we finally went to bed that first night; 4 am? 6 am? I don’t know. Richard took the couch and Penny and I shared the single bed in the room we had rented. I was horny — sure — who wouldn’t be in a situation like that, but I wasn’t horny FOR Penny, per se. She had been a friend for years and aside from having had a crush on her for three weeks in the 12th grade, sucked on her tit once at a wedding as a joke, and one random night where I told her that I had always wanted to eat her pussy after we got a cup of coffee together… aside from THAT, we didn’t have any real chemistry and I didn’t see anything happening.
In bed, drunk, horny, and dumb, however, we had a moment. We were laughing about all the craziness of the night so far and then one of her breasts found it’s way free from her shirt. She didn’t notice — or she pretended not to — and I looked at it and licked my lips. She moved her shirt slightly to cover her nipple and then the other breast was suddenly free.
“Oops.” I said almost innocently.
“Oh no!” She smiled so playfully and invitingly. “What’s a girl to do?”
“It’s too bad you have a boyfriend.”
“Why is that?” She asked knowing full well what I meant.
“Why didn’t he come?”
“He isn’t fun.” She said with a tone of seriousness.
“Well he is missing out.” I was starting to get hard thinking about taking her nipple into my mouth again. “I’m glad you invited me and think I am fun.”
“You are fun.” I think she pulled on her shirt a little and suddenly both of her breasts were exposed.
“I wish you were single.” I whispered back so that her brother wouldn’t hear me. The thought of holding her amazing breasts in my hands and getting my mouth on them working me up even more.
“What if we just pretend I’m single while we are here?” She asked with a mix of innocence and lust. My mind raced. I had hooked up with a married woman once and I still felt occasionally guilty about it; but she had been the aggressor. Likewise, I had once seduced a married woman at a bar, but realized I would feel bad going through with it and instead just fucked with the poor woman’s head. Now I was with a an old friend and wondering if I would be comfortable being the cause of her cheating. I had been cheated on once (probably more than once) and it had really devastated me. Did I want to be that guy?
She eye-fucked me while she pulled off her loose-fitting gray shorts revealing her bare naked pussy. My cock was throbbing. I reached my hand out and took one of her breasts into my hands and squeezed it gently. It was incredibly soft and smooth. I hadn’t been with a woman in over a year — more or less — and this was fantastic.
She moved in to kiss me, but I moved out of the way. “No… no kissing. You have a boyfriend.” She whimpered a little in disappointment. I took her face in one hand and gently turned her away from me as I moved in to kiss her neck. She gasped and squirmed a little and I watched as she reached down between her legs. She started to rub her clit as I kissed from her neck down to her breasts and finally slipped her nipple into my mouth. I flicked at it with my tongue as she increased the pace of her masturbation. I kissed across her chest to get to the other nipple and did the same. Kissed back up to the other side of her neck. Then ran my hand up and down her inner thigh.
She was letting out little moans throughout. They would intensify at the opposite ends of my strokes. When I would reach her knee I would increase the speed of my tongue which was gently flicking her nipple against my two front teeth and she would moan. Then, as I approached her vagina, I would let my fingers linger momentarily at the crease of her leg teasing that I might touch her soon.
She had waited long enough and finally her free hand reached out and grabbed mine, guiding it to her pussy. As soon as my fingertips felt her wetness I knew I was in deep trouble. My inhibitions and insecurity about what was right or wrong crumbled away as I felt the magic of her sex on me. “Oh fuck, you feel so good.” I whispered in her ear.
Her hand reached out and began to rub my erection through my shorts. I was so hard and so turned on that I was worried I might cum in my pants. In order to avoid that, I decided that I just didn’t need them on any more and pulled them down to my knees. She wrapped her hand around my thick member and gave it a firm squeeze. I watched as she looked down at it for the first time and her eyes got wide and her mouth hit the floor. She looked back into my eyes with a look of surprise and I was ecstatic. I’ve always loved the moment when a woman realizes that my cock is bigger than they thought it would be.
She quickly got on her knees and wrapped her lips around me and started to suck. The last time a girl had put my cock in her mouth it had been a nightmare; this was a dream come true. I pulled off her top while she moved rhythmically up and down on my penis so that I could see her big tits swaying back and forth. She reached one hand down between my legs and began to fondle my balls while the other held my cock still so she could find her stroke. She frequently looked up into my eyes to check in on me and make sure that I was enjoying it as much as she was.
It was my turn. I wanted to taste her pussy and see if what I had fantasized about occasionally over the years was actually worth the wait. I pulled her on top of me into a 69 and then touched the tip of my tongue to her pussy and flicked. She moaned and I licked again and again. I grabbed her ass and pulled the cheeks apart then shoved my tongue as deep into her slit as I could. She responded in kind by trying to take my entire cock into her mouth and throat.
We continued like that for several minutes; licking, sucking, rubbing one another. She jumped off of me and lay next to me on the bed like a little spoon to my big spoon and Penny presented her ass. “Fuck me. I want you to fuck me.” She begged and demanded in equal measure. I didn’t have a condom with me so I asked if she did.
“No, I didn’t bring any. Just fuck me. I’m on the pill.”
‘Oh my god,’ I remember thinking, ‘is this a good idea?’ The answer was obviously ‘no’ but I moved into position, rubbed the head of my erection against her incredibly wet pussy until I was good and lubricated, then I pushed myself into her.
“Oh my god!” She yelled out loud as my girthy cock slipped further and further into her. I put my hand over her mouth and shushed her, trying to remind her that her brother was on the couch less than 10 feet away. She nodded in understanding, I took my hand away from her mouth and kissed her neck, then started to thrust my hips into her. I’m obviously biased in my memory when I say this — knowing that it had been 13 — almost 14 months since I had lest been inside a woman, but her pussy was the greatest thing I had ever felt.
I was trying to fuck her slowly so that the bed wouldn’t make any noise. Similarly, I wasn’t trying to rush into cumming early. I wanted to impress my old friend with my stamina and skill. Well the best laid plans of someone who hasn’t fucked in a year were doomed from the start. As soon as I heard her moaning my name and whispering to me about how big my cock was I was done for. I started to hump faster and faster. The bed began to squeak, she began to moan, and I started to unload my balls. I pulled out just in time to roll her onto her back and cum all over her stomach.
It had to have been the biggest, stickiest, load I had made in years and it went everywhere. I hadn’t made her cum yet, so she returned her fingers to her pussy immediately and began to frantically rub one out. She got close to the edge and I started to get turned on again. My cock hadn’t ever gone fully soft after busting my nut, and now watching her about to cum I was fully hard again. I took her nipple in my mouth and licked while she finally climaxed and let out a deep moan, muffled into her pillow.
I spread her legs open and pushed myself into her again. She tossed the pillow away and looked at me in shock. I had cum less than a minute before and was already rock hard. I don’t think she had ever experienced that before. I pinned her down and started to give her my best. The longest, deepest, thrusts I could muster while I stared into her eyes. She came again almost immediately, then again a minute or two later. She kept her head covered with the pillow as she cried out my name in between orgasmic moans of delight and I was elated. This was the kind of sex I wanted — that I needed — after so long away from it.
The bed was going crazy and I was so thankful that her brother was too drunk to hear us. I wanted to cum again and I wasn’t going to stop for anything. When I had enough I pulled out again and emptied whatever was left in my balls onto her tits. I looked down at her, naked, sweaty, and satisfied. She went to clean up and I pulled on my shorts and sat there amazed at what had just transpired. My roommate had been right. I fucked Penny; hard.
Every night for the rest of the trip she and I would find a way to fuck. One night she was in the shower before we went out. I knocked on the door and asked if I could come in “just to pee” as a cover for her brothers benefit. She agreed, I went in, then pulled her ass out of the shower and fucked her while I remained dry on the other side of the curtain. One day while roaming the streets she made out with a girl who she showed her tits to us. Then I made out with that girl. Then Penny and I made out. Then we snuck off and fucked in an alley while people walked by. Most nights we just waited until her brother fell asleep and then would attempt to quietly fuck in the bed so as not to disturb him.
The last night we were going to be there we were at an Irish pub having a conversation about sex. He was lamenting about how horny he was to me and how he really wanted to fuck the girl at the end of the bar. I empathized and told him that I was super horny too and really wanted to hook up with someone. That is when he looked me dead in the eyes and told me to cut the shit.
“Come on, you and Penny have been fucking every single night.”
I am sure my eyes got wide and I bet I turned red in embarrassment. “Oh man, uh, sorry about that.”
“I don’t care, man, you’re awesome. She is awesome. Do your thing.”
“For real?”
“Yeah, just… I dunno. Warn me first or something so I can put in some head phones.”
“Yeah, I will, thanks. Wow.” I bought him his drinks for the rest of the night as a sign of deep appreciation. I told Penny that he knew, that he was cool with it, and that he’d put head phones in to give us some privacy that night. I’m amazed we didn’t rush back to the room right then and there to get started, but we waited and true to his word Richard put in head phones.
Penny and I took that as a free pass to be as loud as we wanted so we didn’t hold back that night. We went full force into loud, nasty, verbal, hard fucking. About half-way through we heard Richard yell out “Jesus-Fucking-Christ, you don’t have to be as loud as you can. I can still hear everything. Fuck!”
We laughed, quieted down a bit, then finished up. It had been an amazing week of drinking, eating, laughing, and fucking. The best possible way to come off of a long intentional dry spell.
When we got home the next afternoon we parted ways and I thought for sure that was going to be that. She had a live-in boyfriend who she had been with for a few years. They lived an hour or so away. We had agreed that it was a “Mardi Gras only” situation.
That night, around 9 pm, she texted me and asked for my address. I gave it to her and she told me she’d be there by 11. 10:59 pm and I hear a knocking at my door; its Penny. She smiles at me, gives herself a brief tour of the kitchen. Then says “Where is your room?” I walk her up to my room, she closes the door, then strips down immediately. She was showered, freshly shaved, and she looked incredible.
“Oh yeah?” I asked with a sheepish grin.
“Oh yeah. You’re going to fuck me again right now. I can’t stop thinking about your cock.”
I was nude a moment later and we climbed into bed. Now, fully unrestrained, I learned what she was all about and it was amazing. We had sex for at least two hours that night and finally finished up with our activities around 4 am when we just passed out. In the morning I woke up with her hands running all over my body while her mouth swallowed my cock. At one point she stopped and looked at me, my cock dripping wet from her saliva, and she said “I wish I had known you had such a big cock. I would have been fucking you all these years. Can we send a picture to Melissa? I want her to see it.” Melissa was a mutual friend from high school who I had also had a crush on at one point and — as I understood it — she had, had a crush on me too.
“Sure.” I laughed as I pulled out my phone. We snapped a picture of her holding my cock alongside her face while she gave a big thumbs up accompanied by an adorable smile. I sent Penny the picture and she immediately sent it to Melissa, then to about a dozen other girls she knew. I was already turned on, but her bragging about my dick to girls I knew in high school was the hottest thing ever. I told her as much and she giggled, then jumped up and sat on me one last time. We fucked until we had both cum and then she got dressed and went to work; I did the same. I was about an hour late to the office, but it was worth it.
She came over every night for the next two weeks after she got off work. As you might guess she ended up breaking up with her boyfriend a few weeks later and then moving to the city where I lived. We entered into a very complex friends with benefits situation which lasted for the next three years. She and I had a lot, lot, lot of sex. I won’t try to recount it all, but I have about a dozen more remarkable stories from my time with her that I will tell over the next month or so. I hope you enjoyed this one and all the stories to follow!
Source: reddit.com/r/gonewildstories/comments/mqvrb7/mardi_gras_aka_the_start_of_the_best_sex_of_my
Hot AF. Looking forward to hearing more about this fun with Penny