Okay. So if you’ve already read my other two posts you already know that I was in the Marine Corps. This story fits in between the two stories already posted to my profile.
After I worked at the 7-Eleven (and the Chi-Chi’s Mexican Restaurant, and the American Airlines counter) in my college town, I ran out of money and joined the military. After a few years in the Marines and taking an early out to go back to school, I took a job as a waiter at a local sports bar/restaurant. During the daylight hours and up until about 10pm the place operated as a sports themed family restaurant with a full bar and menu. At 10pm however, the DJ got to spinning and the place turned into a dance club.
I worked about 6 months before I started to gain a list of regular customers. Being that I worked both the day and evening shifts, my frequent flyers ranged from older couples to young families, to a number of single women. As a single guy myself, I certainly took no issue with the ladies, and there was one in particular that I had developed quite a flirty friendship with.
She was a pretty blonde local girl born in the army town that was the town I went to high school and my first year of college in. Her daddy was a Colonel and she exclusively dated officers. As a veteran Marine Sergeant I was not in her dating pool of qualified male applicants, and I knew this. It was what it was and I accepted the fact that she was just a cool, fun chic who tipped really well.
One Friday night I waited on a party of 8 ladies and she was the party planner. Their table was right up against the dance floor, so I knew that they planned to stay longer than the dinner hour. This could go two ways; lots of tipsy flirty girls who would tip well, or lots of drunk sloppy girls who might just forget to pay their tab. A tactic that we servers would use to ensure we didn’t get stuck with a bill was to close out the dinner tab when the music started, then transition to a cash bar ensuring that the customer paid as they drank. Not great for tips, but at least you got the dinner tab settled and received your money from that service before everyone got silly drunk.
The dinner went well and I made a healthy tip from each of the ladies, especially the blonde. She rounded her tab up to the nearest hundred which in turn ‘no balls’d’ the other girls to be generous as well. No sooner had the dinner bill been settled, the ladies ordered their first round of drinks. All high-end multiple liquor cocktails. $Cha-Ching$
The blonde had first ordered a couple of Long Island Iced Teas, which in 1993 were $5.00 drinks that were served in a tall hurricane glass. For the first two rounds she paid with a ten spot and told me to keep the change, but with the third round the mood shifted. She asked me for a recommendation and I offered her a ‘Sex on the Beach’, another $5.00 cocktail in the same tall hurricane glass. She made eye contact and held it for a few seconds and then agreed. When I brought her the drink she put a $20 in my hand and kind of held it there for a few seconds before taking the vessel and in a flirty way sipped the straw, still keeping the eye contact.
*** Always with the eye contact. If a pretty woman wants me to rob a bank, all she needs to do is look me in the eye, giggle, and in a flirty voice ask. ***
She had two more SexOs before the party was over. On the last round she again paid with a $20 and said, “Call me!’ I looked at the paper in my hand snd she had written her number on it. I kind of laughed and thought to myself,, “No way. She only dates lieutenants.” Yet the tips that she had been giving me all night, the flirty quips, and her locking eyes at every opportunity told me otherwise.
After we closed the restaurant I decided to give her a call. 1993 was just before cell phones became mainstream, so I used the phone at the hostess stand. It was about 1:30am and I didn’t expect her to answer, but she did and she was wide awake. We chatted for a few minutes and she got my attention by describing what she was wearing. She gave details about a pale blue lace teddy. That definitely caught my attention, but unfortunately I was still wearing my work clothes that reeked of chickwn, burgers and spilt beer. She suggested I grab a shower, change and come to her apartment.
I sped home!!! Normally it took eleven minutes to get from work to my house, but I think I made it in five. I ship-showered in two minutes and was out the door by 2:00am. She lived about 15 minutes away and as luck would have it I parked right in front of her place. I knocked on her door and she answered wearing exactly what I imagined based on her very accurate description. She pulled me inside and with no small talk whatsoever she kissed me. I remember grabbing her ass with my left hand and with my right cupped her left breast. Both her hands were holding my face as she started walking backwards into her bedroom. She fell backward onto her bed and pulled me down on top of her, legs hanging over the side with her toes on the floor. After a few more minutes of making out I moved down to her breasts and started sucking her left nipple while she pulled my shirt up over my head and tossed it aside. I reached down and popped the snap on her teddy so I could play with her pussy. After a few minutes of sliding my finger up and down her folds I and lowered my face down to her soaked crotch and licked her freshly shaven pussy while inserting two fingers and massaging her g-spot, alternating my thumb and tongue gently on her clit. In no time she was having her first orgasm and I was still half dressed.
She reached up and undid my pants and my cock sprung forward. As soon as my 501s hit the floor she pulled my body back down on top of hers and I thrust myself deep into her pussy until I hit bottom. She first let out a long moan as I entered her, followed by a slight yelp when I could go no deeper. I remember holding it there for quite a few seconds keeping the pressure on her cervix with the head of my cock. After those few long seconds I started pumping her pussy rhythmically, building up the pressure in my balls. Her hands were laced around the back of my head pulling my face down into her neck. I remember kissing, nibbling and biting her gently, driving her wild while trying to kick my pants off of my feet. 😄 She was moaning and talking into my ear telling me to fuck her harder. After three or four minutesvof constabtvstroking I couldn’t control myself any longer and just when I knew I was about to cum I pulled out and shot a hot stream up and onto her upper belly and boobs. After four or five good pumps of cum she pulled me back down onto her chest where I could feel my hot wetness between the two of us, making her firm tits slippery as we kissed and made out again before I pulled my kegs up around her hips and covered her body in mine
We laid there on her bed, her teddy pushed up and down into a pale blue roll around her waist, my pants on the floor at the foot of her bed. Exhausted, we drifted off to the sounds of each other’s heavy breath and and didn’t awake until the birds started chirping. When we woke up, things became awkward. Her tone kind of changed from sexy and flirty to ashamed and businesslike. I took the cue and got dressed. When I was ready to leave she walked me to the door and with a gentle kiss she pressed an envelope into my hand and whispered, “This is for cab fare.” I told her that I drove my car, but she shrugged it off and said to keep it anyway. We kissed again and I slipped out the door. I suspect that she wanted me gone before the neighbors were awake to see me leave. When I got to the car I backed out of the parking spot and left her lot to head home. At the first light I thought to look in the envelope and inside there were two $100 bills.
She just paid me $200, plus all the tips at the restaurant the night prior, to have sex with her.
So, in an effort to wrap this up I’ll say that this turned into a once a month thing. I think that she was too stuck-up and wrapped-up into being an officer’s kid that she wouldn’t commit to actually dating an enlisted man. Instead, every few weeks she’d come to the restaurant and drink a lot, tip heavy, and in one way or another tell me to call her. Most of the time we’d meet back at her apartment, other times we’d meet at my place, and a couple times she’d gotten a nice room in one of the better hotels in a town that was not well-known for having nice hotels. We actually connected a little bit and had sone great conversations and really got to know one another. Unfortunately (for me) she never wanted ro meet during the week, or even go out on a real date. This “relationship” lasted about 18 months and always ended in the same way, an envelope by the door with two $100 bills inside.
Our connection ended after one particular erotic meeting where we actually spent a whole weekend in an old stone cabin by a river in the Wichita Mountains. After we cleaned up and packed up on Sunday she told me that weekend was to be our last meeting. She had been dating an army lieutenant for about a year and he’d asked her to marry him and she said Yes. And with that, it was all over. She cried a little bit and hugged me tightly and apologized for whatever it was that we had developed. We kissed goodbye and parted ways and never saw each other again.
I don’t know if it was irony or forgetfulness, or what; but she forgot to pay for my cab fare for that last meeting.
Source: reddit.com/r/gonewildstories/comments/sfg9mu/did_i_tell_you_about_the_time_i_was_a_male_hooker