So, back to the tale of my first pay-for-play session...
I forgot to mention earlier that I actually made my initial call to Susan from my workplace, and that our appointment was during my lunch hour.
Lunch hour arrived and I swung by an ATM, then made my way to Susan's "office" (she'd answered the phone saying "Tenth Street Counseling"), situated in what appeared to be an old-ass Victorian house located in the SOMA district of San Francisco. Not a posh neighborhood by any means, but not a combat zone either. I quickly scanned the immediate area in front of the house for undercover vice cops on stakeout (like I'd recognize them) and went up to the door. During this entire time I was hot and flushed like a guilty schoolboy. Two trains of thought careened through my head; one was an absolute conviction that everyone on the street knew I WAS GOING TO SEE A PROSTITUTE. The second was something like "OhmyGod I'm gonna get laid get laid get laid..."
I pressed the buzzer and after a moment the door opened slightly; a tall blonde woman in her (I'm guessing) early 30s with a half-asleep expression peeked around it. "Hell-o," she said in a singsong lilt. Only her face was visible; I'm guessing this was a protective measure on her part; she'd be able to slam the door on me if I did anything crazy.
"Hi, how you doin'?" I said. Looking back, I know I didn't exactly come across as friendly, but that's because I was scared. Was someone else waiting just inside the door with a knife/gun/lead pipe? Were vice cops moving in to bust me the second money was mentioned? And most importantly, was "Susan" a guy? (Yes, I'd seen RISKY BUSINESS)
Susan opened the door wider and let me in. We were at the bottom of a staircase. "It's nice to meet you," she said, and closed the door behind me. "Come on up." She headed up the stairs and I could see that she was about 5' 9" with generous healthy curves in the right places. Not a supermodel, but not bad either. She looked like an office worker in a long-sleeved blouse and sensible skirt and shoes. As I followed her up I got a perfect view of her ass, which swayed with each step and was nice and round. I thought about reaching out and grabbing it, but refrained. That might not be cool, I thought. From my viewing of WORKING GIRLS, I knew that these ladies didn't appreciate being treated like meat.
We ended up in a thinly carpeted room that was empty except for a futon on the floor, an electric clock, small easy chair, and a music box that had one of those jointed cutout clowns in a window that danced when a drawer was opened (I'm not sure what that was for). The shades were drawn and the room was dimly lit thanks to a small lamp next to the futon.
I sat down on the futon. Susan slipped her shoes off and sat on the floor next to me. I got a better view of her body and could definitely tell she wasn't a guy. And her ad hadn't been lying about her being busty. Through her blouse, I could tell her tits were generous...not massive, but still an ample size.
We made small talk. About what, I don't recall. Susan then told me, in a polite but all-business tone, that I could either pay her now or afterward. Wanting to demonstrate my good faith, I handed her my five 20s. She put the cash away while I confessed my fears about being busted or attacked. She smiled and put a reassuring hand on my thigh. "There's nothing here that's going to hurt you," she purred, "shall we get comfortable?"
I knew that was the cue to undress, and did so without hesitation. Even though I was getting more excited with every passing second, I was still nervous. This was, after all, my FIRST TIME. Susan took off her clothes and at last I got to see those tits of hers. They were full, pendulant, and topped with large, yummy-looking nipples and aureolae. She sat down next to me on the futon.
But there was still more business to take care of. "Do you mind if I check you out?" she asked. I consented, a little confused, but then she took my cock in one hand and the small floor lamp in the other. Training the light on my schlong, Susan examined my little soldier with a clinical eye. She even squeezed the head gently so my peehole opened slightly. She was examining me for signs of STDs. What a smart, careful girl.
"Everything okay?" I asked.
She released me and put the lamp aside. "Yeah, you look great," she said. Susan sighed a porno star's faux sigh of pleasure, took one of my hands and put it on one of her tits.
Game ON!
I practically lunged forward and started kissing and fondling her tits, savoring the feel of them, like firm balloons, in my mouth. After 25 years of drought, I was getting TITS AT LAST! I kissed her neck, working my way upward.
"Do you mind if I kiss you?" I asked.
"Maybe when I get to know you better," she replied matter-of-factly. I was disappointed but knew that kissing was considered off-limits in this arena, so I resumed feasting on her boobs and sliding my hot little hands all over her body.
After a few minutes, Susan asked, "Do you want me to give you a treat?"
I KNEW what she meant. I was going to get a BLOWJOB! "Yes," I panted.
Susan then picked up a condom from next to the clock and opened it. With practiced movements I would go on to see demonstrated by many more escorts to come, she slipped the condom over my cock with her fingers and mouth. She then started bobbing her head up and down as I grew bigger. Her mouth felt warm.
I couldn't believe it. A woman was sucking MY COCK. Wow.
Several more minutes went by, and then Susan lifted her head and asked, "Do you want to try something else?"
I answered in the affirmative. She lay back and parted her thighs, using two fingers to spread her pussy lips open. I awkwardly got on top of her and she helped me insert my semi-hard penis into her.
Because I wasn't fully erect, I didn't get the full effect, so to speak, but it was enough. I slid onto her and slid my hands under her arms, grasping her shoulders as I humped her, panting hungrily.
"I want you to come," she gasped, "I want you to come now."
I'd like to say that I lasted a long time, but I didn't. I came in about a minute. But I didn't care. I was now officially NO LONGER A VIRGIN!!!!!
We uncoupled, I pulled off the condom, and Susan lit a cigarette. "Is this the first time you've had intercourse?" she asked.
"Yes," I replied, still glowing in the triumph of having gotten laid at last.
We chatted a little more until I noticed my hour was just about up. We both got dressed and she gave me a hug. "Come see me again," she invited. I said I would, then practically floated down the stairs, out the door, and back to work. I was sure everyone could tell by my face that I'd finally FUCKED A GIRL. I remembered the movie DEAD POETS SOCIETY where Robin Williams tells his students about something called "Yawp!", which represented a feeling of overwhelming exhilaration.
Well, that's how I felt. YAWP!!!!
I would go on to see Susan several more times over the next couple of years. She would introduce me to the joys of eating pussy and tit-fucking. Although we never did make out and I never got to do things with her (or to her) that I'd do with other escorts, she was an excellent first step on my sexual journey. Last I heard, she'd left the business and had finally realized her goal of becoming a therapist. I'll always remember her with fondness...and a big hard-on.
November 14, 2007
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