Surrogate Boyfriend

Waiting for my order in Armin's Lebanese deli, I got to thinking that one really nice thing about working as an escort was that the money I was making let me eat a whole lot better. Working at below minimum wage and doing odd jobs, I'd eaten lots of oatmeal, bought day-old bread and carried a bag lunch to work. Now I could just bike over to a deli and order a pastrami sandwich and salad -- no sweat. After the session that morning with Maureen, I'd worked up a pretty good appetite for lunch and Armin's generous portions were welcome.

Eating lunch alone is a good chance to people watch. But today, my mind was going over too much stuff to concentrate on folks coming in and out of the deli. First there was reminiscing over the morning's fun with Maureen in the break room at the J&B office. Other stuff though wasn't quite so pleasant -- mainly the thing with Fatim and what the hell was Wasim up to. I'd have to come to grips with that if another date came my way.

Intending to go on a couple-hour bike ride that afternoon, I biked back towards home to change into shorts. Passing the J&B office, something seemed amiss, but I couldn't figure out what the hell it was. Jolene's Mercedes was there as usual because she would have to be back from her meeting. Maureen's Chevy was there and some other cars as well. I rode on a little further and it came to me: The black BMW sedan and a gray Chevy Suburban didn't belong there. I turned around and from across the street watched the J&B office for 15 or 20 minutes and snapped a few shots with my cell phone camera. Nothing seemed out of the ordinary, but I still wasn't satisfied. Somehow those cars had the look of trouble. I rang the office on the pretense of not being sure about the time to meet my Friday client who I was to escort to a party. Maureen answered. From the tone of her voice I knew that at least nobody was getting beaten up so I decided to let things go and write off my near panic to nerves.

Friday

There was no convenient bus line going anywhere near the TGI Fridays where I was supposed to meet the client named Kay, so I ended up taking a taxi. Kind of high class for me but what the hell, the $30 taxi was small change compared to what I'd get as a 'tip'. I walked in shortly before six and scanned around for a brown haired woman wearing black slacks and a white blouse and sitting alone. Maureen hadn't told me the client's age or if she had long or short hair or if she was thin, fat or in between.

Beyond that pretty basic description and that the client's name was 'Kay', Maureen had told me I was supposed to be her date for a party and to dress smart casual -- jacket but no tie.

Walking in, I told the hostess I was meeting someone and proceeded to scan around. Not seeing anyone likely, I swallowed my male-never-ask-for-help pride and went back out to the hostess. Based on the sketchy description of the client, the hostess, after asking my name, pointed out a booth occupied by a brown haired woman who appeared to be around 30. Apparently Kay had told the hostess she was expecting a guy named Ralph.

With good looking clients, like Audrey and Marilyn, it takes a while to find out why they'd ever need or want to hire an escort. Audrey, the Silicon Valley executive was an alpha type who loved having power over men, at work and at play. At the same time, she had a big need to let off steam. Marilyn, married to a gay senator, just needed a man to appreciate her lovely body.

With others, it's no surprise that they go the escort route. Like my first client, Denise, late 50's and carrying some extra pounds, her cardiologist husband preferred the juicy pussy of a young nurse. He couldn't service both and Denise had to do without. The bottom line is, there are women who just can't bop into a disco and get picked up. So when they really want to get serviced, they have to go to outfits like J&B.

Kay fell into the second group, but not for reason of age or fat. No, when I got closer, my initial impression of her age - 30ish -- was confirmed and she wasn't overweight. No way. Big boned for a girl perhaps, but not fat. She was one of those women who aren't ugly, but still wouldn't make many men turn their heads either.

Her long brown hair was pulled back severely to end in a pony tail, her complexion, while not blemished was on the ruddy side and her eyebrows were almost non-existent. Some women overdo the makeup business. Not Kay, she was just the opposite. She was dressed in a white long sleeved blouse and black slacks. The black matching jacket lay on the bench beside her. It looked to me like she had come directly from work. All in all, a plain Jane who wouldn't have a bunch of guys buzzing around her at a party.

Her blouse showed protrusions, not big, just big enough that they might get the attention of some really horny engineering student. Trouble is, for plain Janes like Kay, in a city like Baltimore, there's plenty of real classy looking stuff around and plenty of that classy looking stuff has nice tits too.

I introduced myself as Ralph, gave her the J&B card and asked if she were Kay.

She put on her dark rimmed glasses (that too) and turned to look at me and the card. "Yes," and after an awkward pause, "Please sit down," and with her hand indicated the seat opposite her.

I tried making some small talk -- like how crowded the place was, the traffic, weather, etc. but didn't get much more than a 'yes' or 'no', only occasionally a whole sentence. For me things were getting awkward and I pretty quickly realized that aside from her poor grooming, there were other reasons why she needed to hire an escort if she wanted to go to a party with a date. I was reminded of the story about Larry King trying to interview Robert Mitchum.

Patience and ideas running out, I decided to ask Kay that old favorite American opening line question: "What is it that you do for a living?" This question is frowned upon in polite society and really turns some folks off, but not Kay. Just the opposite, that's what made her finally open up.

A senior associate with a big law firm (I'll call it 'ABC Partners' for convenience.) in Baltimore, she specialized in defending corporations against health and personal injury claims. Having read lots of John Grisham novels, her being a senior associate in big law told me a couple things: Kay was indeed around 30 and she put in a 60+ hour workweek.

After she started opening up about herself, I hardly got in a word and mostly nodded my head and did my best to look sympathetic and admiring. In a nutshell, she had graduated 14th in her law class at Columbia and had passed the bar exam in New York and in Maryland -- on the first try in both states. She was hoping to become a junior partner before the year was out. It didn't surprise me when she said that her work week was generally over 70 hours.

With that kind of work load, her appearance no longer surprised me -- hell she wouldn't have time to work on that too. And of course, even if she were pretty, she wouldn't have much time to meet men. The time factor alone would just about explain why she needed to hire an escort to accompany her to a party.

I finally got in my sympathy line: "Gee, you don't have much free time for hobbies, socializing with friends and such."

Then the dam broke. Like some clients, she felt the need to explain in depth why Kay had ended up needing to engage an escort.

"No I don't have much free time, not since high school. Well actually, I didn't have that much of a social life in high school either. At University and then at Columbia Law School, I did nothing but study, never had dates. My last real date was in high school. The long hours really got long after I started at ABC, work and more work, then studying for the bar exams. Well I just haven't had time to meet anyone. But even with all the work stress, there is social pressure at work, like people ask if you're with someone. I always had to say 'no' because there was no one. Then I got the feeling, actually even heard from other associates, that the partners thought I might be lesbian. ABC has company social events, you know, picnics, barbecues, that kind of thing. I've always had to go alone."

"Kay, so what if you were lesbian? Good grief, this isn't the 1950's. And it seems like you've worked like hell and billed lots of hours."

"Look, I'm 36 and still haven't been made a junior partner and I haven't been let go either. That means there's some strange reason why I don't get promoted even though the partners like my work." Then the flood started. Choking back sobs, she went on: "It suddenly occurred to me that I wasn't getting promoted because they thought I was lesbian."

That's when I started understanding why she needed a date for this particular party. "So this party we're going to, there'll be people from your office there and I'm going to be like an alibi boy friend, someone you just met and fell for?"

"There'll only be people from the office there. With their spouses or partners of course, and no same sex couples. And by the way, you won't be someone I just met."

To myself: "Oh fuck!" Out loud to Kay: "Oh, you mean we've been dating for some time?"

"For almost a year."

The evening was getting to be disappointing. For one thing, it was looking like there wouldn't be any big 'tip' for my special services and secondly, I wouldn't get to put it to a woman who must be just plain starved for a good fuck. Covering up my disappointment and hoping to allay my concerns about having to play the part of her long term boy friend. I asked her what she'd told her colleagues about me -- like where we met, how long ago, what I was, hobbies -- all the kinds of shit that comes up at a social engagement.

Kay ignored my question and went on with her story. "As soon as I realized why I wasn't getting promoted, I made up a story about meeting someone from out of town and whom I didn't see too often. That took some pressure off and seemed to put me on track to partnership at ABC. Unfortunately, colleagues and even my boss started asking when they would be meeting 'Randall' -- that's the name I invented for my phantom boyfriend. At company events, I always said you were out of town, but someone can be out of town only so many times. I've run out of out-of-towns, so Ralph, you're just going to have to be 'Randall' tonight."

I'm used to using aliases and at least my J&B name 'Ralph' and Kay's 'Randall' both started with an 'R'. More of a problem was fitting in and making conversation at a party. "And what does Randall do for a living? Just in case somebody asks."

"Randall is an independent real estate broker, whom I met last fall while shopping. He works mostly in Florida and the Gulf coast of Georgia and Alabama and is away from Baltimore a lot of the time. Ralph, I think it would be best if I start calling you 'Randall' right now, okay Randall?"

Given my history of being at large, using an alias was about the least likely way I could screw up while acting the part of her phantom boy friend. I quickly agreed to be 'Randall'.

More troublesome was that someone might trip me up with some detail about the business I was supposed to be in or just some simple inconsistency. Kay must have given this all lots of thought because she quickly came back with a few lines to say like how I couldn't say much about what I do because of the confidential nature of various clients and the sensitive nature of the negotiations. She also said that it shouldn't matter much because talking about work at these social functions was frowned upon anyway.

It got me to wondering what I could talk about. I read newspapers and sort of keep up with current events, but I don't do any of the yuppie sports like golf, tennis, squash and such. True, I bicycle, but for that I ride whatever Marvin lets me use. If any of these lawyers are into biking, they're going to be riding $5000 marvels of machinery. And I don't know shit about music -- old or new. Come to think of it, I don't even follow any pro sports. I didn't let on to Kay about any of the possible traps because by now it was pretty clear that based on the time we were going to be together, there was a good chance there'd be a 'tip' in it for me.

Then she gave me some rudimentary background information on Randall -- age, birthplace, where I'd grown up, education, etc.. By that time we'd been in the TGI Fridays for well over an hour and I told her that with the party, we'd probably run over the 4 hours that her deal with J&B covered.

"Of course I know that, Randall. I also realize that the arrangement with J&B doesn't cover all activities that a couple might engage in. Look, if we've been seeing each other on a regular basis for 8 months like I've been saying at work, well that means we're intimate on a regular basis. Now we can't make up for the past 8 months, but I think we should have sex at least once before we go to the party."

A half pint of blood must have surged into my pecker and my earlier disappointment evaporated. I recommended that she take the all night plan and told her about the few things I wouldn't do -- like anal and man on man.

Her answer was very straightforward: "Let's go to my apartment and I'll give you the $600 there." Outside she led me to her white BMW. I declined her offer for me to drive (without mentioning that I didn't have a driving license).

In the luxurious white leather seat of her BMW, I managed to get my hard-on somewhat under control and was able to walk normally by the time we got to her place. Inside her pricey upmarket apartment, she gave me the $600 and then there was an awkward moment - both of us knew what was going to take place but neither knew how to initiate it.

It was Kay who broke the awkward silence. "I have some condoms in my bedroom." Then after a short hesitation, "And some lube too." Seeing my look of surprise, she went on. "Look you do have a really big one, don't you? I mean seven and three quarter inches is pretty darn big."

My jaw must have hit the floor. Of course people expect that a male escort is going to be well hung, but she knew my length exactly as it was entered in Dr. Henley's medical report!

Seeing my surprise, she continued, "Randall, it's on the J&B website." Seeing my still open mouth, she went on. "At the lower left corner of the page with your photo -- in small type 'UC-LH734LS514'. What else could 'LH' mean but 'length hard'?"

That was a real surprise. I had looked at my web page, but mostly at the photo with my face blurred and the description with stuff like 'mature, physically fit, comfortable in sophisticated environments, etc.'. Everything else on the page, like that line of small type, I'd thought was just IT gibberish.

I just had to ask the big question. "So you picked me because of my size?"

"No. I picked you because all the rest of the escorts were too young. Look, part of the story I've made up about Randall is that he is older, like over 50, and divorced. The first time I saw your photo on the website, your hair was all gray and you wouldn't have passed for 50. Now with the brown on top and frosting on the sides, well you're perfect. Look Randall, for my purposes, size isn't much of an issue. Besides some of the younger escorts were almost as big. And for your information, the fact that you're not circumcised didn't matter either."

Again seeing my surprise, she explained: "You see Randall, 'UC' has to mean 'uncut'. You're not circumcised, are you?"

By then I'd recovered my cool and told her she'd just have to discover my penile condition by observation.

"Well Randall, let's get on with it, shall we?"

Young lawyers with big law firms really rake it in and her apartment looked like it. Not being a home decorating expert, it's pretty hard for me to describe but what really struck me was that even with a big king size bed, there was still lots of room in her bedroom. Kay turned back the covers and then turned back to me, "I once read there was a time when young married couples who'd never done it before would, for that first time, undress themselves in private and then meet face to face. I'd like to start that way. You go in the bathroom and undress while I undress here. Oh, and please bring one of the big bath towels. There's no use messing up the sheets."

And so it was, Kay was standing by the bed naked when I walked back into the bedroom with a pretty good hard-on for her to admire. She continued staring at my crotch as we got closer together and then said, "Oh Randall, you really are big!" Then grasping my shaft and working my foreskin back and forth, "And you really are uncut too."

By this time I'd taken in her appearance too. She must have noticed me staring at her breasts. "I keep them locked up under a sports bra. In law school, guys who asked me out always turned out to be more interested in my titties than in me so I got in the habit of hiding them."

It wasn't hard to see why a guys might be interested in her tits. Not being an expert, I couldn't judge whether they were C or D cups -- all I knew for sure was that they were generous enough for some real pleasant tit fucking. Looking further down, I could see she wasn't into shaving either. In fact she wasn't into trimming either -- her dark brown pubic hair extended out to where she'd not want to wear a normal swim suit.

In a way, we were like two eight year olds playing 'If you show me yours, I'll show you mine'. Kay obviously wasn't getting much sex but she knew enough to know my pubic hair had been trimmed and she was self conscious about her un-groomed twat. Looking down, she stammered: "I can't get it right doing it myself and I somehow never get to a salon to have it done. Oh Randall, I hope you don't mind too much."

I knew I had to give her mood a boost so I just said it looked like a nice cozy place to be and then I rubbed my dick all over her hairy crotch. That seemed to give her the boost she needed and she came right back with her next proposal.

"Randall, after we do it, do you think you could trim me a little?"

I told her it'd definitely have to be after because as she could see, I couldn't wait much longer.

Kay spread the bath towel on the bed and pushed the covers further out of the way. "I think I'd like it if we do it pretty much the normal way, I mean me on my back and you on top." Now over her earlier lapse into feminine weakness, she said it more like an order than a suggestion.

I was right behind her as she lay down and she barely had her legs apart and I was between them on my knees and putting on the condom. I thought she might be ready but when I tried, the head of my dick encountered a slit that was barely moist. "Kay, it's not going to work very well this way. We need to slow down a little."

"You mean like foreplay?"

I moved away and lay down beside her. "Yeah, that and maybe some mood making. Music. Lights down a little." I knew I'd need some lube too but I didn't want to tell her that right then.

She got up and went to the living room where her radio and CD player was. By the time she came back in the bedroom, some kind of soft classical piece was playing -- and playing very nicely -- she had dough and she didn't mind spending it on good electronics. After switching off all the lights except a little bedside lamp, she lay down again on the towel. I put a hand on one of her generous breasts and fondled it lightly before moving to the other one. That seemed to put her more at ease so I played with one of her nipples and suckled the other. It was pretty obvious that her equipment hadn't seen much action for some time. I wondered what I'd be hearing when she started talking about her sex background as all clients eventually do.

When Kay seemed more at ease, I reached down and found a slit that was much more receptive than before. Going in to the labia brought the first real response from her -- shorter breaths and more moisture. I started wandering around with my finger, working my way up. Circling her clitoris brought sharp breaths and even more moisture. Continuing to suck and kiss her nipples, I went for her vagina and put a finger in. That brought a shudder and a nice "Uhhhh-ahhh" from her so I proceeded to fuck her with the one finger. This got her hips rocking nicely but before I could move up to two fingers, she interrupted with "Randall, I'm ready!" and she spread her legs wide apart. I wasn't sure she was really ready but the customer is always right so I backed off and again got on my knees between her legs. After putting a little YES on the condom that was still in place, I entered her. This time I was able to slide in without too much resistance, first halfway and then after lots of in and out action somewhat further. Normally I like to have a woman go off first, at least once and more if it's in the cards. Unfortunately an orgasm on Kay's part just wasn't in the cards and I finally accepted that and let go. Even though she didn't get off, she did act as if she enjoyed having my dick jerk as I filled up the condom's receptacle.