Getting with the Waitress (M/F)

EDIT: HOLY SHIT thank you for all the positive feedback and the well wishes for the fate of this relationship.

My friends and I had been drinking at our go-to spot, a mellow bar to play pool and watch a game. One had just broken up with his girlfriend and the rest of us were on “Don’t let him make an ass out of himself” patrol.

A little back story, we have been regulars at this spot for a couple years now, most of us work within walking distance and, as such, Friday night we all meet up. This bar has a waitress that takes care of the pool table area and after at least 100 Friday nights together her, Amy, and I have developed a little rapport. She is not my type but undeniably attractive. She stands all of 4’11”, blonde hair, super petite, her breasts barely fill your hand (more on that later), each cheek of her ass is a handful, but both look quite full on her small frame. She has a very thin gauge ring in her nose on the right side. We are always friendly with each other hugs when I walk in and leave, we talk about each other’s lives etc, it is safe to say that we are friends.

I’m an ok looking guy, all-around average, I was a swimmer in high school and I still have some residual muscle definition after college and re-upping my time in the gym. I’m about 6″1′ with dark hair, and am 24.

Back to Friday night, it had gotten late, far later than my group usually stays. We were trying to coax my friend to leave but he wasn’t having it and we got stuck there until last call. The others all lived the same direction and I lived the opposite, I was in the process of getting an Uber when Amy offered to give me a ride. We made our way to my apartment, there was a spot in front and she pulled into it and shut the car off, “You know, after a night of serving people drinks, I could use one myself!” I invited her up. All I had to offer was beer and whiskey, she opted for a cold beer. We sat on the couch and she scooted up close to me. “I’ve wondered about you”

“Not much to wonder about I’m afraid.”

“No, I mean, I’ve seen you in my bar with a couple different women in the past…”

“Exes… now at least”

“You guys just keep to yourselves, you don’t really try to meet anyone, not that my bar is known for single women our age”

“Well, I have learned that I am not the best at “picking up” women… I found that all my relationships come from knowing her for a couple months and getting to know one-another before we date.” The glass of whiskey I poured myself was making me talkative, “We ended up at your place because it is a nice mellow bar, the drinks are good, the prices are cheap… I mean the service is terrible, but we suffer through.”

“Oh, its that bad uh?” She said shifting herself so she was kneeling on the couch, looking right at me. She wrapped her arm around my neck.

I moved in for a kiss, we started to make out on the couch, I tugged her tank top up, reveling a pair of pierced nipples. She let me take it off but said, “I’ve been at work since 6, do you think I could, maybe, rinse off in your shower before we…?”

“Only if I can join you!” To be honest, I needed a rinse too.

We left a trail of clothes to the shower. Suds covered our bodies, I played with her small breasts and pierced nipples as I washed her body. She rubbed my cock with the suds, I got hard rather quickly despite all the alcohol. “Wow, that’s pretty nice” she complemented, I am just under 7 inches (but since this is GWstories we’ll round it up to 14 inches and thick as an eggplant). She knelt down and began sucking the head and stroking me after rinsing the soap away. I cradled her head in my hands as she did, she reached down and rubbed herself.

“Let me take care of that,” I said as I guided her up. I ran my hands down her sides, and seeing the height difference I suggested we go to the bed. We dried off and I lifted her up, gripping her cute little butt. I lowered her so she was easier to carry, but she gasped

“Don’t not yet, I am soo not ready.”

“I wasn’t going to sweetheart” I said giving her a reaffirming kiss as I carried her to my bed. I kissed my way down her body. Giving her nipples and stomach all the attention they deserved. I kissed and flicked her skin with my tongue all the way down to her moist lips, and teased around them. I kissed and licked until she reached down and pulled my head into her and made me work my tongue into her depths. She was already soaked so I worked a finger into her then another, I moved my tongue to her clit.

“No don’t make me come yet, I’ll tighten up and we can’t fuck then.”

I moved back down away from her clit and focused on loosening her up with my fingers. I did this for a few minutes before she pulled me up and said she was ready.

I kissed my way back up to her nipples and tugged on the little barbells through them. I propped myself against the headboard, spread my legs so her hips would land between them and let her mount me, facing me but we were in a very wide V shape. She was far enough back that her G-spot was riding along my cock but close enough that I could run my hands along her body and she could hold herself on my arms. She slid down onto me, very slowly, I could feel pressure on my tip as it reached depths that my fingers had not. Her hips hit mine and she sighed, “Holy shit, I am full.”

“Good baby, is it to much? This is a deep position”

She began riding me slowly, gently, she was focusing on her own pleasure, which was fine by me, her rhythm was perfect, she was riding the full length of me. Her hips moved her entire body as she rode. I didn’t focus on any one part of her body, giving affection to her cute tits and sides, and stomach and arms and hips and legs. Her paced increased, she began breathing more sharply, I saw her abs clench and feel her box tighten around me. She dug her nails into my biceps as she rode her way through her orgasm. She sat on me for a minute before the orgasm subsided then lifted off of me and laid down on my chest.

“Oh my god baby, that was incredible.”

“Good sweetheart, that’s what I wanted to hear.”

“I know you didn’t come, give me a minute and we can go again,” she said before kissing me and stroking me.

“I’m ready whenever you are.”

After sometime of making out and jerking me off, she rolled onto her back and pulled me onto her. We got into missionary, I slowly pushed into her. She let out a deep breath, then wrapped my hips in her legs. I slowly worked into her. She began to moan and rub her body, she leaned her head back to kiss me. We were wrapped in a passionate embrace, I could feel her start to come again, she grabbed my head and bit my lip as she rode out another orgasm.

I pinned her down full depth as she madly kissed my neck and chest. “On your back, its time for you to come.” She mounted me in cowgirl and rode me, slowly at first but she picked up the intensity very quickly. I gabbed her little butt with both hands, she leaned in grabbed my chest. She started talking dirty, begging me to fill her with cum. I grabbed her breast with one hand and kept a tight grip on her ass with the other. I started pumping into her and almost instantly felt my load leak out. She hopped off and cuddled up with me.

“Do you think I can have one more orgasm? Can you just rub my clit with your load in me, pweeeeeaaaase?”

How could I resist. I rubbed her while kissing her and she had one final orgasm. We made out for a while before falling asleep.

The next morning we cleaned up and went to breakfast, after a shuffle of her giving me a ride back to my car, then her going to her place to change, then coming back to my place, then breakfast. After breakfast she spent most of the day at my place talking. About sex, what we like what we don’t. (She likes anal, jackpot, in like 3 months after she “gets ready” but jackpot). We 69ed our way to one more orgasm each before she had to work at the bar. We met up for dinner Monday night, and had a real date.

That’s everything up to this point. I really hope I’m not shitting where I eat on this one, literally I eat at this bar, their boneless hotwings are killer.

Source: reddit.com/r/gonewildstories/comments/4zauuk/getting_with_the_waitress_mf