Heya! So a little about myself:
I’m currently in a committed relationship with a man who I love very much. We’ve been together for two and a half years and still going strong. The road that led to this relationship however, was very rocky.
After a two year relationship ended with a guy from university ended, I let go and played the field big time. Most of my hookups were with guys I knew (some exes) with a few one night stands scattered in-between. This story starts when I first felt some form of attraction to my current boyfriend.
I was 24 at the time and he was 33. We both worked in the same company and started a month apart. At first, we worked on different projects and never spoke a word to each other. We noticed each other, but that’s as far as it went. At the time we were both in relationships.
A few months in, I break up with my then boyfriend. I was emotional for weeks afterwards, until I got a message from an old friend. I was an emotional mess and craved comfort; though this story isn’t that important, so long story short, he fucked me the next day. This continued on for a week or so, until I moved onto the next friend, and so on. Two months go by and on my 5th guy (Tinder, eugh…). These sex sessions were nothing more than void filling (no pun intended), feeling a few moments of bliss when cumming, then feeling like utter shit afterwards, but that all changed at the company Christmas party.
I dress myself up; Some subtle makeup, a modest black dress, heels and just a touch of cleavage. I’m ready to go get completely fucking wasted (Gotta love a free bar!).
The evening starts slowly. Everyone is just mingling and stuffing their faces at the fancy buffet. Two hours in and a good few of us, myself included, are clearly drunk. My manager (35 at the time) and I have been chatting for a while and the conversation turns to subtle flirting. He’s not all that attractive, but hey, I was drunk, still craving male attention and he was an older authority figure and I found that insanely hot.
He picks up on my subtle flirting and begins to flirt back. It becomes inappropriate very quickly, which instantly turns me off.
I said something like,
“You look very handsome in that suit.” Feeling his arms and giving his muscles a light squeeze. “If you weren’t so much older than me, I’d definitely ask you out on a date.”
To which he responded,
“That’s a shame. I’d love to loosen that tight pussy and ass of yours.” He said while brushing my hair aside with a finger (douche chills).
I stood there, stunned and replied,
“Oh.”
I walked away.
Now, I know what you’re thinking. I started the flirting hoping for it to go a certain way; Yes. However, I do like a build up and this was a complete turn off. If this was said after a nice, slow build, I’d have been back at his place letting him do exactly that. Anyway….
So now I’m drunk and I’m pissed off and rambling on to people how he’s an asshole without actually telling them what had happened because, you know, I didn’t want to be outed at a slut. Then I notice him, my now boyfriend, Paolo.
I approach him and begin babbling away like a drunken fool, giving him hugs, saying “MERRY CHRISTMAS!” Obnoxiously loud because of the music currently playing which wasn’t all that loud. Never in my life have I seen someone slow blink at me before and I just start laughing incessantly. I calm down and we actually have a pleasant conversation. He had a girlfriend at the time, which made him a no go, but god fucking damn did the idea of him cheating on her with me made me noticeably wet.
I find out he’s 33 and that was it. The seed was planted and it was growing fast. Throughout the night we got very comfortable in each others company (alcohol, baby!). We danced, drank some more, danced again, drank again and again (I’m sure you all get the picture).
Some time into the evening, we have a conversation with a woman at our company who was about 6 months pregnant. Don’t worry, she wasn’t drinking alcohol. I notice Paolo staring at her very large pregnancy tits which were sitting proudly on display being hugged by a ridiculously tight dress, with a silver buckle holding the cups together for dear life. Paolo is trying his hardest to keep his eyes off them, bless the poor man, but it was just too much for him. Every 10 seconds, and his eyes were right back there. She noticed this immediately, but didn’t seem bothered in the slightest. We kept sharing looks, her smile stretched across her face every time.
Now it was time to put an end to this because I needed him focused on me.
“They’re lovely, aren’t they? I said.
Paolo’s eyes widened.
“Huh? What?” He replied.
“Lana’s breasts. They’re lovely, yes?” I said grinning.
Lana giggled while Paolo shifted awkwardly.
“No, what you mean? No, I mean they’re great.” He stammered.
Lana and I erupted into laughter while Paolo laughed, completely embarrassed. Lana adjusts the buckle tucked underneath, her tits jiggling as she did it. Paolo’s eyes go straight back down.
“Just give them a squeeze and get it over with!” Lana teased.
“Ok then!” I replied. I cupped them and gave them an jiggle and Paolo looked like he wanted to cum in his pants.
We grab some shots, down them and head to the dancefloor.
We casually dance for a little while and then it gets sexual real fast. I’m swaying my hips and rubbing my ass lightly against his hip. I run my hands through my hair, looking over my shoulder at him seductively. I keep checking my surroundings and everyone is so drunk they’re all dancing away.
I start to body roll, pushing my ass into him each time. He starts to run his hands up and down my waist and hips, lightly gripping my soft parts. I begin to slut drop, running my hands in between my thighs each time. I make sure to keep looking over my shoulder at him, he’d look right into my eyes intensely. His hands moved onto my ass, rubbing my cheeks gently. Goosebumps covered my arms ang legs and I felt him fingers caress me. I pushed my ass into his crotch and felt his erect cock digging into my cheeks. He pulled me in hard, his hands wrapped around my waist. I reach around, planting my hand on the back of his head and pull him in.
I speak directly into his ear over the loud music,
“How would you like to come back to mine for some more drinks? I have a bottle of rum waiting to be opened.”
“I’m supposed to be going home. My girlfriend will be expecting me.” He responded, loosening his grip and dancing casually, looking around to see if anyone had noticed us.
“You’ve already cheated on her. Your cock has been pressed into my ass for the past 5 minutes. What’s a few drinks with a colleague?” I replied.
My heart was pounding. I knew what I was doing was wrong, but if he was more than willing to reciprocate, it was worth going for.
“Just tell her you’re gonna be out late and you’ll stay at a friend’s. You’re having fun!” I suggested eagerly, sliding my fingers across his hard cock that was bulging in his trousers.
He left the room to make the call.
I saw Lana sitting by herself so I went over to chat.
“Heya! How’s it going ‘Lovely tits!'” I joked.
She grinned and raised her eyebrows up and down.
“I chose the right dress then!” She giggled. “He’s a lovely guy. I eat lunch with him every day. He’s really sweet; he’s always checking I’m ok, helping me up from my seat, treating me to lunches now and again.” She pats her big pregnant belly.
We chat a little bit about her pregnancy and I shift the conversation back to Paolo.
“You looked like you were both having a good time on the dancefloor.” She probed playfully.
“Oh god.. I was checking constantly to see if anyone had noticed.” I replied, face palming.
“Oh no no, please don’t be embarrassed! I wasn’t judging. I’m glad you both had a good time, Paolo especially. He deserves it.” She said.
“What do you mean?” I queried.
“He’s been having some relationship issues. He’s been with his girlfriend for 14 years and it’s fizzled out basically. We’ve been talking for a few weeks about it and it sounds like it’s gonna be over.” She said.
“Oh, that’s makes sense..” I responded.
“Yeah. They’ve just existed with each other for the last 6 years and they never have sex. Last time was three months ago when we last spoke about it.” She paused, “Don’t tell him I said that.” She asked.
“Don’t worry, I won’t say a thing.” I said reassuringly.
Paolo returns some time later.
“It’s all sorted out.” He announced.
The night goes on for another two hours, with subtle flirting as we weren’t as private as I first thought. The evening simmers down and people are beginning to leave. We say goodbye to Lana, exchanging hugs and kisses. She whispers something in Paolo’s ear before he leaves.
“Let’s get a taxi away from the club. We don’t want anyone seeing us getting in together. Just to be safe.” I suggested.
Paolo agrees and we get a cab a few minutes away from the club.
On our way back to my place, we waste no time getting to know each other a bit more. His hand is running up and down my leg, inching ever further up my dress.
“So, what did Lana whisper to you before we left?” I asked.
“She said to have fun.” He replied.
I leaned in and whispered,
“I’ll make sure you do.” Licking his ear lobe right after.
He cupped his hand on the side of my face and began to kiss me gently; his tongue lightly brushing my bottom lip. Within seconds, my tongue was in his mouth and our hands were all over each other. I could see his dick running along his leg, struggling to escape. I rubbed it firmly and felt it twitching. The heat radiating from it was intense. He teased my inner thigh with his finger tips and worked his way up my dress. They explored my region, a finger lightly tugging at the lace of my thong. I squirmed, breath escaping my mouth in between each pass of his tongue. He never made contact with my clit and it drove me wild.
Finally we arrive at my place. We hurry inside and head straight to my bedroom. He lifts me up and throws me on the bed. We hastily throw our clothes across the room, stumbling about like the drunkards we were. Finally, my dress is off and his tongue is all over my. He flicks the tip over my nipples, squeezing them firmly between his finger and thumbs. Waves of heat rushed through my body as all my senses went wild. He works his way down my body and to my inner thigh, still licking and kissing my tingling skin. His fingers hook around my thong and begins to slide them down achingly slow. I shift my hips to encourage him, but he just slows even more.
“Lick my pussy now!” I begged. “Please, lick my pussy!” I growled fiercely, pulling his head into my vagina. He planted his lips on my clit and held them there, gently sucking it in and holding it between his lips. A gasp escaped my lungs and shook from head to toe. My back ached and I’m grasping the sheets with all my strength.
“Please please please PLEASE!” I whimpered.
He began to suck my clit, flicking it with the tip of his tongue each time. My hips dropped and I came; back arching and mouth agape, my thong hanging from one knee. I lay there, panting for a few moments while he kissed my inner thigh and stomach.
I sat up and pulled him towards me. His dick was standing to attention, peering up at me and then I noticed. I sat there slowly stroking it, the long shaft twitching as my fingers did their thing. He’s a 7 and a half incher. I’m used to guys who are average or just above, 6 being about the biggest.
“Oh wow… I’m a bit afraid!” I joked.
He looked concerned.
“Umm, we don’t have to if you don’t want to.” He responded.
“Oh shut up and just fuck me!” I demanded.
I reached into my drawer and pulled out a condom. I opened it and placed the condom on the head of his dick. I rolled it down about half way. He took over and managed to squeeze himself in. He lay me back and spread my legs apart. I pulled him in and he slid inside me.
“Take it slow..” I whimpered.
He inched his way in until he was fully inside me. I let out a sigh of relief and started grinding with his slow, steady pumps. Whilst I was riding the waves of bliss, I felt him start to lose his rhythm and go soft. The condom, plus the alcohol was taking it’s toll.
He slipped out of me and started to work his dick. To keep up the pace, I took over and slid the condom off and took him in my mouth. That did the trick. His cock swelled in my mouth as I took long, hard strokes.
Rock hard again, I kept my rhythm going until he stopped me.
“I’m going to cum, please don’t let me cum yet.” He pleaded.
I obliged. He reached into my drawer and took another condom. I was so fucking drunk and so god damned horny I just thought “Fuck it” and told him to “Just fuck me.”
I lay back down and he slipped inside me again and began thrusting. I was close.
“Fuck me harder. Just fuck me, please fuck me!”
He started thrusting harder and faster until I came. He slowed down.
“Don’t you fucking dare stop! Don’t stop!” I demanded.
He continued to thrust hard until I went floppy. I braced myself and awkwardly spun around. I felt him slip out of me, precum sticking to my inner thigh. I spread my legs and pushed my ass up and presented myself to him.
“Take me.”
He slid in again and bam; he hit a spot I’d never felt before.
“Oh fuuuuuck.. Right there, right there right there!” I screamed.
I could feel him begin to swell.
“I’m gonna cum, oh fuck I’m going to cum!” He panted weakly.
And just like that, I came. HARD. My body quivered and my legs gave way, shaking violently. I collapsed and his cock slipped out, slapping my ass cheek on the way out. His dick quickly found it’s way between my ass cheeks accompanied by a warmth running between them and onto the small of my back. I felt a spurt hit my asshole, another skimmed my cheeks and another hit my pussy lips. It pretty much glazed my ass like a Krispy Kreme doughnut.
I lay there, my legs quivering still from the explosive orgasm and they felt weak for about half an hour later. We lay there, covered in each others cum.
The next morning, went woke up pretty late and went out for a late breakfast. We talked about the night before and how much fun it was, but decided it would be best to leave it at that.
At the time, I didn’t have any strong emotions towards him as I was still very much in my sleeping around phase. But that sure was a lovely Christmas present.
Source: reddit.com/r/gonewildstories/comments/p1wy5i/a_breakup_between_me_f_and_an_ex_m_partner_leads
Did you ever get Lana anything for being an awesome wing woman?
Fucking hot story. Hoping for some more.
Very hot well told story, thank you!