From Escort to Altar
By: Date: 2021.08.19. Categories: Sex Stories Tags: , , ,

OK I admit it, the first time she went out with me I had to pay for it. Although not a hooker she was close to it, she is what she called a paid escort. I had another big company dinner I had to go to and again no date. I actually saw her ad on (escorts ads site) as I waited for the bus and with nothing to do as I bided my time; I read and reread her ad a hundred times. “Escorts by Nancy, need an escort call now and book a lovely friendly escort to accompany you to that function you dread. Don’t go alone pick up the phone.” It seemed to be talking just to me, so as the bus pulled up I jotted the number down and while I rode downtown I fantasized about the lovely Nancy.

The more I thought on it the more the idea intrigued me, after lunch, I called, getting an answer machine telling me to leave a number, and they’d get back to me. I left my cell and then tried to get it out of my mind so I could get some work done. By the time they returned my call I was already home from work and had almost given up hope. I found myself nervous as I talked to the woman on the phone yet she was very pleasant and did her best to calm me down. I told her what I was looking for and that my escort had to fit in with the parameters of a black tie business dinner. Once I paid with my credit card, I was instructed where I could pick up my ‘date’ for the evening.

I hate to put myself down but to be honest I would have to be called homely by anybody’s standards and I realize this is the main reason I have so much trouble with women. It’s not that I don’t think there are women who could love an ugly man it’s just I couldn’t seem to find them. So here I was picking up a date I’d bought and paid for and I was still so nervous I could feel the sweat running down my spine. I met her at a bar downtown and I felt like a stupid school k**, I just hoped she couldn’t hear my knees knocking.

I was the only guy wearing a tuxedo in the bar so she had no problem picking me out of the crowd. She came up to me with the nicest smile anyone had ever given me. I introduced myself and put out my hand; she wrapped my arm around her waist and reached up to kiss my cheek. She therefore took my awkward move and turned it into a romantic gesture just as graceful as a swan. She told me to call her Melinda and I figured it must be alias, it wasn’t until later I found that was her real name. She was not beautiful but not plain either and then there was that smile, it was the kind that could brighten a room. She did look handsome in her gown and I was very happy with what I had arranged.

We stayed for a drink and to get a chance to know one another, I was surprised how easy she could draw conversation out of me. I guess she was so at ease she had a way of relaxing me as well. It wasn’t until we were at the dinner that I realized our talking had put together a database for us to use for dinner conversation with the other guests. Melinda took a night of rubber chicken and stale speeches and turned it into a night of magic and mystery. As it turned out the night I had been dreading for weeks was now ending too soon thanks to her, I had enjoyed myself and I know she had impressed my co-workers.

After dinner, they had a ballroom set up with a live band for dancing and cocktails for all. I hadn’t planned to attend that part of the evening but Melinda said it sounded like fun so off we went to the ballroom. You can add dancing to the list of things I’m socially inept at but with Melinda in my arms, I felt like I was gliding on the dance floor. If we weren’t dancing and someone would ask her to dance she would refuse as if being away from me for just the length of a song would be too long. We stayed until the band shut down and I heard ‘last call’ just as they do in the movies.

Once in the car I asked her where I could take her, she hesitated leaned over, kissed me, and then asked me if I would take her to my place. At first, I was in complete shock and then I remembered I was with a professional and if she was coming home with me for sex, it just meant more money for her. I’m sure it wasn’t my first faux pas of the night but I do know it was my biggest as I asked her how much it would cost me. When I looked over and saw her crying I knew I had really messed up. I told her how sorry I was that I wasn’t insensitive just ignorant. I was so surprised when she reached over and kissed me again. She said she deserved what I asked but that the escort part of our date was over and now it was just a date.

Once in my apartment she took the lead, as she knew she must. Although this was not my first time with a woman I was still too shy so while I sat on my bed she undressed in front of me. Not a strip teases but still slow and sensuous and as I looked at her nakedness I became greatly arroused. Once down to her dainty panties and bra she started on me, kissing me as she undressed me. I was in total humiliation as I ejaculated as soon as she grasped my penis but she seemed at ease with this and as she cleaned my issue with a Kleenex, she told me to relax; I would be hard again soon. She then took her under things off and we lay together kissing and rubbing our bodies against one another. It didn’t take long for me to be erect again and once she put a condom on my member, she mounted me, sliding me inside her with ease. With her hands on my shoulders holding her up, she stared into my eyes as she slowly rode me. She anticipated my climax and smiled at my satisfaction as she offered me her breast as I came again. Melinda spent the night and we made love many more times each one better that the previous.

In the morning as she showered, I made us a simple breakfast and as we ate, she told me her story. I simply came out and asked her why she was here with the likes of me. Melinda told me I reminded her of her first boyfriend, shy and somewhat awkward but with a good heart. It seems that was not enough for her back then and she left him with a broken heart to find someone better. She said she found better looking and more suave but none with a heart as pure. After searching, she realized what she really wanted was her first love but now he had someone else and was happy again. It seemed to her that love was currently lost to her and as she ambled from romance to romance, somehow she just ended up in the escort business. Melinda said as soon as she saw me standing in the bar nervous as a boy at his first prom; she could tell my heart was pure.

It is so hard to believe that night was over a year ago and how much my life has changed since then. Melinda and I are now engaged; just being with her has given me so such more confidence that I’ve had two promotions since we’ve been together. As for Melinda, she quit the escort business and is now in PR work and with her social skills; she is just skyrocketing in her company. When I think that I owe all this to just glancing up to notice an advert on a lamppost it somehow makes me believe in fate.

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