Paying For It

Sat, 08/03/2013 - 20:06 -- jcartwright

As I alluded to in my earlier stories, although I have had a lot of good luck in the swinging lifestyle, I've also on more than one occasion pursued encounters with sex workers. Moving in this world is fraught with moral contradictions and I'm not entirely proud that I have so much experience in it, but it is what it is (I'd be glad to take questions / criticism in the comments...dialogue's what O.org is all about, no?). For the most part these liaisons have been fairly routine...not really worth relating as a story, but there are a few exceptions....

About three years ago I spent a significant amount of time travelling for work over the summer. I was stuck in the same hotel in the same suburban area, with nothing within walking distance (not even a hotel bar) and nothing to do. My ads on swingers sites and Craigslist just weren't getting any bites, and so I started trawling through the local escort ads on Backpage to see if anyone caught my eye. One ad really stuck out - an African-American woman, mid-20s, with a slightly Asian cast to her features. She had beautiful perky breasts (this was before Backpage started cracking down on ad photo content) tipped huge brown nipples, and a nice curvy figure - soft but not fat, with a killer ass. I picked up the phone and was greeted by a sexy voice, "Hi, this is Angel..." We agreed on a time and and a price, and she told me to call back right before I left to get directions. Soon enough I was showered and heading out with directions to the motel. Another call once I got there to get the room number and I was heading up the elevator...No matter how many times I do this that trip from the car to the room is always such a rush. Is it a sting? Were her photos real? Will she be clean? God I'm so hard...damn I need this...

I arrive at her door...it's open a crack and I walk in, closing it quietly behind me. Angel lives up to her name...if anything she looks even better than the photos, and she's freshly showered, wearing a sexy blue teddy that reveals as much as it covers. She's short (maybe 5'3") but gorgeous and everything about her screams sex. Her breasts swell under the sheer fabric, and her matching lacy thong peeks out below its bottom edge. I walk up and give her a hug, pressing into her, so she can feel my erection, and without a word give her a kiss...it always puts folks at ease, cops don't touch. I pull away and ask if I can wash up - "Sure honey, feel free" - she smiles and points me to the bathroom and I drop my envelope on her dresser as I go to wash my hands. When I return it's gone, and she's laying on the bed, waiting, gorgeous...mine for the hour.

My clothes are on the floor by the time I make it to her...no point in being coy, we both know why I'm here. I stand next to the bed and she rolls over and takes my cock in her mouth, her lips surrounding me, taking me in. I notice that the wall behind the bed is fully mirrored...it's a thrill to see her sucking me from all angles, her mocha skin such a contrast with mine...I lightly rub her back with my fingertips, pulling up her teddy to expose that gorgeous ass....she arches her back, languorously responding to my touch. I'm now rock hard between her lips, and she stares up into my eyes as she envelops me in her soft, wet mouth. I'm so close but I don't want to cum yet...I pull out..."Can I return the favor?" I don't know what she'll say...most women in this business like to keep things under control, but some enjoy a little reciprocation.

Angel rolls over pulls down that sexy little thong and spreads her legs for me, exposing a neatly trimmed landing strip over bare pussy lips. "Yes honey...I want you to taste me..." I kneel between her legs and start to tease...when I give oral I love to take it slow...I kiss the hollow of the inside of her thigh...lightly glaze her clit as I move to the other side...nibbling, licking, taking in her clean musky scent...I slowly part her lips with a finger, waiting for her to say no, but she just moans a little as I slide into her wetness...I move my tongue to her clit now, teasing still, but serious now...I can tell she's enjoying this, he clit is swollen, and she's wet...so wet...she bucks against my finger as I tease her clit with my tongue, up and down...suck it lightly between my lips...varying the pressure, then slowly, steadily side to side, as I finger her. She starts to moan...a deep, throaty sound...I can feel her pussy contracting as she presses against my face, her hips up off the bed...she bucks up once, twice, three times....then collapses back into the bed, pressing me away from her with her hands. I pull away, my mouth covered in her juices....

I grab a condom from the nightstand and slide it on...it's my turn now. She pulls off the teddy..."How do you want me?" I tell her to turn around and put her ass in the air...I've wanted this since I saw the mirror...I watch us as I position myself behind her....her breasts hang down, she's gorgeous...I can see the look in her eyes as I position my cock between her lips, and slide into her wetness...she looks a little sad, but needy...she presses back into me and I don't care anymore...I grab that amazing ass in both hands and start to pump...her breasts sway with each stroke, and we get into a rhythm...I'm not holding back, I need my release...with a grunt I thrust in again...she knows I'm cumming and she's a pro...she moans and milks me with her pussy, pressing hard back against me, taking me as deep inside as I can be....my cock throbs again and again, shooting into the condom...a last twitch and I'm spent. I grab the base of the condom and pull out...the tip is filled with my cream, the outside covered with hers...I toss it in the trash and we make small talk as I clean up...she slips into sweats and a t-shirt, domestic now, and turns the channel to MTV - "True Life" is on. We hug, and I head out, back to my empty room.

jcartwright's picture
James Cartwright

Just like to write about sex and relationships!