(M)y lovely night with the shy (f)emale waitress.

Hi all, here's a little background on myself so you can picture what I look like. I'm a 6'1 205lb shaved head white male. More on the side of stocky//muscular but slightly chubby still ( broad shoulders and big arms/chest from weekly lifting session at the gym the past 4 years ) but also have a good bit of fat ( okay well 20% isn't probably good ).

Last year I got a job helping manage a small hotel up north in the United States. I had been working there about 4 months and the GM//owner decided to open up a restaurant in it – waitresses galore! Right!?

As started our round of interviews, myself , the GM and assistant GM interviewed this one girl – Erica. She was your average white girl – 5'5, average face, blue eyes, probably 140-150lbs ( not a flat stomach but just enough padding there to look attract myself ) , and in her mid-20's. The thing that stood out most to me was her long sunny blonde beautiful straight hair. You could tell it was natural and very straight, it came down to her upper back. Usually women's type of hairstyle doesn't do much for me – but this woman's hair gave her like 3 or 4 more points on the attractive scale.

She was well articulated, and educated during the interview, had just graduated from a local college with a degree as an English major. She was hired on the spot.

As the restaurant opened and I got to know her and all the other waitresses , she stood out differently in a few ways. She was very quiet and shy, but on the other hand very smiley and polite. She would never start conversations or hardly speak very much, very introverted – but was the best worker we had by far.

Fast forward a few months, the GM//owner decided to throw a staff party for all 8 of us in his huge summer vacation house an hour away. Everybody had their own room assigned for them for the night so no one would drive drunk. Little did we all know the GM//owner loved to drink and partied very , very crazily for a dude in his 50s.

Everybody arrives at the staff party. There's two couples, myself, Erica, and two other attractive single waitresses. Throughout the night, after everyone was drunk out of their mind we all hit the hot tub. This is where I start my flirt game and see which waitress I could hook.

I start off by tickling the cute older brunettes feet in the hot tub, which she is laughing hysterically and sitting on my lap in the hot tub. I didn't want this one though – I wanted the gorgeous blonde Erica – so the whole time I'm making eye contact with Erica. I eventually push the brunette off me and motion Erica over to me. I start to escalate with Erica and give her a nice massage on the shoulders. She's in this tight , maybe too small blue polka dot bikini. As the hot tub fun goes on, I start cupping her beautiful smaller B cup breasts under the water – but very stealthy and no one could see me doing it. I could tell she was liking it but she didn't want to get caught and smacked my hands away after a few seconds every time.

As everyone got tired and more progressively drunk, the partiers started going upstairs to their respective rooms. I had a room that was two down from Erica's. I made it up to my room before hers and was just kind of just hanging outside of my door. As soon as she made it up the stairs I called out her name and she gave me the bedroom eyes.

" Erica come to my room and lets watch some TV " , casually slipped off my tongue. " Okay but I'm going to go change first , I'll be there in a second ". A few minutes go by and I hear a knock and open to see this gorgeous blonde standing outside of my door in some short pajama shorts and a large college T-shirt. I take her hand and lead her to my bed. I have the TV on just for comfort, because her and I both know what's happening next. As she lay next to me I start to caress her thighs and I see the pent-up horniness in her eyes coming out. Before we start making out all of my 5.5 inches is already rock hard from months of no sex.

I quickly take off her pajama shorts and get no resistance. So I continue and remove her big college sweatshirt all the while trying to hide my eagerness to fuck this lovely woman. Underneath she had a matching black bra and panties – it looked like she had planned for this night.

As I take off my shorts and my cock bounces out she lets loose a fucking bomb. " I hope you don't mind that I'm this easy " Erica let out. I go blank and ignore it – she didn't at all seem like a party-type slutty girl. Whatever I think, I'm not passing this one up.

I put her in missionary and grab her legs at mid-thigh, admiring her beautiful pussy with it being bare all but a small line of blonde that matched the hair on her head, and entered my raw cock. In my horny state of mind that night I forgot to buy condoms….

Erica's pussy gripped my cock and it felt amazing – I hadn't been laid in probably 6 months at this time. She had her eyes closed and would bite the side of lip lightly and would give off these quiet soft whimpers the whole time I fucked her. I continued to pump away for a few minutes and then decided to take off her bra. She had small, but nice lovely round very perky B cups. I sucked on her nipples for a few minutes then went back to fucking her.

After about 20 minutes of pounding her out in missionary and kissing her simultaneously I pulled out and let loose a stream of cum on her cute stomach. Erica got up and the whole time my eyes were transfixed on her lovely round ass as she femininely strutted to the bathroom to wash off my cum.

We talked for a bit and then decided to go to sleep. About three AM I woke up and turned over and saw her sexy ass in her panties and bra just quietly sleeping. " Hey Erica wake up for a sec " I poked at her gently. " Whaaaatttt " she groggily asked. I started to make-out with her and quickly started tugging at her panties to fuck her again, and was met with no resistance. I ended up fucking her missionary again for about 20 minutes this time before I came on her stomach but I missed a little and got some cum on her black bra. " You asshole! " she exclaimed. I laughed it off and got her a towel from the bathroom and rolled over and went to sleep.

We ended up sleeping together about 2-3 times a week from this point on for about 6 months until she moved and the sex was pretty mediocre. She was very vanilla in bed, and actually turned out to be quite the prude. The greatest thing was every time we hooked up after the first night she let me give her a creampie when I had to finish. Then I'd watch her clench and strut while her cute ass jiggled to the bathroom to get rid of my load. I can't help but find this insanely attractive and it drives me nuts – on the other hand I'm sure the woman in her shoes is pretty grossed out. Thank god for birth control….

We lost contact a few months ago after I started hooking up with another girl and she just fell off the face of the earth. I hope everyone enjoyed it , this was my grand story of how I fucked the quiet, shy introverted waitress.

Source: reddit.com/r/gonewildstories/comments/34awla/my_lovely_night_with_the_shy_female_waitress