Exactly What I Want

When my wife and I had split some years earlier, we remained pretty close. Then the cancer came, and when it was all said and done, she was gone for good, I was really upset, and quite a bit more wealthy. Those first two pushed me to do something for myself - it had been a hard year and I wanted ... something easy to take my mind off the pain.

So I did what anybody with money, a broken heart, and a hard cock would have done: I found an escort in Vegas, negotiated exactly what I wanted from her, down to a specific set of text instructions I wanted followed, and set a date for an extended several day trip out to take my mind off things.

I'm in my 40s. I'm not fit, though I'm reasonably attractive. Back home, I've got a lot of very supportive friends and, while I'm not attached to a specific partner, some of those "very supportive" friends were casual sexual relationships. I have a pet theory that people who don't get married and make it to their 40s are too set in their ways to want to be tied down, so the loose sexual arrangement and commitment work out pretty well. Maybe I'll write about that someday.

Despite the options I had at home, I was a little stuck. Having the conversations about some of the things I explicitly wanted from was hard and embarrassing, so I didn't have them. Don't get me wrong - the sex was great. But everyone's got that specific thing they like to have done and I'm kind of a coward when it comes to confrontation and vulnerability, so the "anonymity" of meeting up with an escort really appealed to me. Instead of worrying about the give and take of equity in my friendship/relationships, I was able to just dictate what I wanted dispassionately. And, mostly over text.

My millennial heart couldn't be fuller, and if I'm being honest with you dear reader, my cock couldn't be harder. This was somewhat of a relief. The danger of erectile function is always one of those boogeymen floating around in the back of your mind as you get older, and gone were the days of my rock hard cock that could go for 3 rounds a session. I could still get hard and fuck for sure, but I had to be careful that I didn't lose it midway through. The viagra helped, but condoms are real tight.

I'd chosen the spring for my trip and when I stepped off the plane, it was just showing signs of the sun setting through the huge airport windows. Moving to the carousel to grab my bag, I saw her for the first time in person. I'd seen pictures, obviously, as we'd chatted about the various logistics.

She stood a bit shorter than me, and I was average height. Shoulder-length dark hair curled a bit to her shoulders. Large dark eyes set in a smooth, pretty symmetrical face scanned the crowd looking for me. It was a gorgeous face. Her breasts were on the smaller side, held back by a tight white shirt with a good view of her cleavage. She wore a mid-length miniskirt (as requested) and low-heeled, open-toed shoes at the bottom of her long, smooth legs.

I'd popped a pill on the plane and could feel just a little movement in my pants when I saw her. When I approached and she recognized me, her face lit up in a smile. She walked forward and pulled me into a tight embrace. This isn't something I'd asked her for, actually, and it gave me the intense feeling that it wasn't necessarily about the weekend, but more a tender gesture of sympathy for the hard year I'd had. The contact flooded my cock with blood - and when she felt it through my pants, she ground a little into me and made a soft noise in the back of her throat.

We separated just in time for my bag to slide by and I grabbed it. She looked down at my pants and the slight bulge that had was just barely noticeable there. Her head moved up and she met my eyes and she smiled again.

"Nice to meet you in person", she said. Her voice was low and slinky. "From your erection, it seems like you like what you see. Good. I'm Maria. Let's go, James." Her mention of my erection, something I'd specifically asked for, kept me hard as we walked away.

I liked when women talked about my cock, and specifically, when they talked about my cock being hard. There's something about the scenario when a woman has to deal with my hard cock that turns me on, so casual conversation mentions about the pure physicality of the arousal, being treated almost like an animal with sexual urges, was immensely erotic to me.

She turned and led me through the concourse and I followed behind stealing glances as her tight ass as we moved. Her skirt, through some magic I didn't quite understand, bounced high as she stepped, revealing the back of her thighs. We arrived at an escalator heading up to the next level in the parking garage, and when we were both on, she took three more stairs ahead of me, so that from my angle, I could see the white panties she was wearing as they peeked out from the bottom hem of her skirt.

I loved seeing up a woman's skirt. Or up their small nylon shorts. Stealing those glances, imagining what lay beneath. Pointing at something through the window, she widened her stance slightly so that the smooth fabric of her crotch was visible, laying tight against her pussy.

This, also, was requested. Maria knew her business.

We reached her car, or her rental car, I wasn't sure how that worked exactly, and after stowing my luggage, she took us from the garage toward the hotel we'd be staying at. We chatted lightly about the city as we drove, and while stopped at a light, she asked "Do you still have an erection?" I told her I did. "Let me see the bulge in your pants." And I spread my legs slightly for her to see the bulge. "Good."

Maria parked at the hotel parking, using some pass she had. We moved to the lobby, I checked in, and while getting keys and signing papers, she made sure to move back into me, pressing into my groin with her ass. My cock had been hard since I saw her in the airport and she was still checking. It throbbed.

In the elevator, she played with her skirt a little bit, raising it an inch or two to expose more of her thighs. "There's something freeing about wearing a skirt", she purred to me. "There's just so little fabric between your pussy and the world. It's just so... available. How is your erection? You've been hard for a long time now, I bet you need to ejaculate and get some relief. This teasing is going to make it a big load, I bet." I shyly agreed.

With a chime, the elevator doors opened and we walked the few doors down the hall to our room. Pushing our luggage in, the door closed behind us. While I was parking my suitcase, she came up behind me and put her arms around my chest.

"I think it's time I see this erection and what I'm working with. I'm going to make you ejaculate and I want to see how big the load is." Her hands drifted down and she unbuttoned my pants. She slid them down my legs and I kicked off my shoes as she guided them over my feet. My cock strained against my boxers.

She reached around and caressed it. "Is this as hard as it gets?", she asked. And when I nodded, she made another sultry noise in the back of her throat. She slipped a hand into my boxers and rubbed my cock gently, getting a feel for it. "I want to see", she murmured suddenly, and spun me around. Her hands lifted my shirt above my head and when it was free, hooked into the waistband of my boxers, pulled it away from my straining hardon, and pulled them down as she had with my pants, squatting in front of me. Her skirt had ridden up and I could see her panties.

When she was finished undressing me, she came back up slowly. Running the tips of her fingers across my thighs as she did so. My cock was leaking precum. My balls were high and tight against my body, and when she laid eyes on them, she tutted. "We'll need to make it a little warmer in here for these guys. I want to see them relaxed when I empty them. I love to see them jump when men cum." My cock involuntarily flexed.

"Oh, do you like that?" She hadn't stood all the way, and she was about level with my cock now, though she hadn't looked directly at it. Her attention had moved from my balls to meeting my eyes. When I looked down at her, I saw her face framed on one side by my penis, which was slowly throbbing in time with my heartbeat.

Her eyes drifted down my chest, stomach, and then finally to my dick. "Oh my my, look at this hard, pretty thing. He looks so angry." Her fingers brushed the shaft lightly. "This is a good erection. Average size, average thickness." She licked her lips. "I can't wait to feel it ejaculate." She stood fully then and gripped my cock hard, pulling me toward the bed. "Wait here. Don't move."

I heard her step behind me, into the tiled bathroom floor, and rustle with something. She came back a moment later, unfolded a towel onto the bed, and gripped me again. Guiding me by my cock once again, she lined me up to stand in front of the towel she had just unfolded there. When we were in place, her grip switched from pulling to a slow jerking motion.

"Mm. Circumsized. I prefer my men cut, you know. When they're hard, I like looking at the head of their cocks." She smeared some of my precum around the head and started rubbing in. I groaned.

"I bet that feels good after having this stuffed in your pants that whole flight." Her other hand reached between my legs, flitting across my taint briefly, and rubbed my tight scrotum. She pinched a little to pull it down feeling the skin reform in her hand. "And I like this hairless scrotum. You missed a few hairs, but I'll touch them up later."

She worked me that way, hand sliding down from my glans to the shaft as she jerked slowly for minutes. It didn't take long. When she sensed the oncoming orgasm, she increased her jerking speed and let go of the pinched skin of my scrotum, but palmed my balls gently. The first pulse came and I sprayed cum all over the towel, shooting further than I had in years. She cooed in delight as the rest shot out in a series of mind-numbing pleasure.

My legs thrust me forward into her hand and she kept pace with her jerking, getting everything out. When my orgasm was spent, she continued to rub my penis as it softened.

"That's a good boy. Judging by the quantity of cum, you definitely needed that." She still hadn't let go of my cock, though she rubbed it more gently as it deflated back to its resting size. I panted and caught my breath, and sighed.

She pushed me down to the bed, laying me down perpendicular to the bed's normal sleeping orientation, and she scooted down to look at the towel.

"Wow, that was a lot of cum. Is it always like that?" I shook my head slowly, still trying to recover fully. "Well, I guess I'll see next time if I can get more." She wadded the towel up and tossed it to one of the chairs in the room. Moving to one of the walls in the room, she added a few degrees to the thermostat and then joined me on the bed, propping herself up on one arm, looking at my soft cock.

"It's not very big when it's soft, is it? You probably couldn't even guess the size it is when it's hard by how soft it is now." She was right - soft, it was pretty small, and even hard it was probably a little below average. "But, I kind of love it."

Her hands drifted down and started massaging the entire area - my pubic bone, the sides of my thighs, my balls. As the room warmed, by sack got looser, and she became more focused on my balls, again, by request. They rolled in her hand, she pressed into the sack and felt the tubes inside, mapping them with her fingers. "Your balls are pretty big, especially compared to your cock. I bet they make a lot of sperm."

I lay back and just closed my eyes as she massaged my genitals. She scooted back a little bit and put her back to the headboard, draping her legs across me. When I turned to look at her, I could see up her skirt, and to the panties there. My cock started hardening at the sight.

She grinned, nodded to my crotch, and asked: "Do you like what you see?" and she widened her legs slightly. My erection bloomed again. "I guess you do, judging by your erection. She motioned for me to scoot slightly diagonal to bring my cock in reach of her hands, which wrapped around my cock again and started to jerk. "I want to see it from this angle this time. I want to see the cum fly out of your pulsing cock, watch it spray all over your stomach when you ejaculate. I want to see your balls pull up and unload that sperm into your vas deferens and you try and instinctually mate."

This is exactly what I wanted. She didn't even look at my face - she was fascinated by the whole sexual mechanics of my penis. Shifting, she moved closer to my cock to get a better view. Holding the base, her hand slid up the length with a strong grip.

"Think about me simulating a pussy with my hands. Your cock doesn't know the difference - it just knows you need to ejaculate. I want to see it. I want to see your cock try and impregnate something - show it to me." I was in heaven. She wanted to see what I could do, and in a few moments more, I obliged.

My orgasm came at the top of her stroke and I could feel more than see, the long stream of cum that shot out of the head. She giggled and kept stroking, milking the splashing cum onto my lower stomach. Being the second orgasm in so many minutes, it wasn't nearly the volume, but I'd learned that my body loved cumming and my second orgasm (and subsequent throughout a day) was better than the first. Again, as the moments ticked by and my orgasm ebbed, she didn't stop stroking until I was completely soft.

"I love seeing the ejaculate fly out of the head. Watching it pulse, seeing the pleasure there and the shooting cum. And, look at you. Covered." A hand cupped my balls. "And these guys feel a little lighter. Are they sore yet?" I shook my head.

"Well, let's get you cleaned up and see what else we can get out of them."