James, Anal Exploration Ch. 01byMalone_Thomas©
It was getting warm. The garage is usually a cool place but our make out session made it seem like a closet. The more I tasted her peach lip gloss on my tongue and her hands all over me the more the stagnant air receded into the background. The beads of sweat were starting to form on forehead, and my back, and my thighs. We were in the garage attached to Jessica's parent's house. We had come home for Thanksgiving, but even in our late 20s felt strange about having sex just down the hall from her parents. The garage had been our retreat for at least a couple of visits, and we didn't hold back on our exploration even there. Jessica and I had been together for about four years. A size 14, so not small, and five foot ten, with shoulder length curly brown hair. She had good size but worked it well. I loved her large breasts and the way her ass gave me just enough to hold on during sex. But tonight I wouldn't have much time for grabbing it.
The couch was old. Brown leather and it felt warm and sticky against my forearms. Jessie was on her knees behind me, caressing my inner thighs. l looked down between my legs and watched her French manicured nails as her hands went up and down my thighs and covered my hardening cock. She moved my thong to one side and I felt as the lace stretched across my cheek. She ran one solitary finger down the crack of my ass. I arched my back. The pleasure was almost too great. I was still ashamed to show how much I enjoyed it. We began this experimentation with my ass innocent enough, during a random session of sex after a night of drinking. Then, her finger, finding her way to my hole during head . . . and I immediately loved the sensation of being penetrated. We experimented more. And the toys got bigger until the inevitable introduction of a strap-on. Though I didn't want to consider myself gay, I could not resist the urge of having her soft body on top of me and attached to a dildo I had already found so intensely gratifying.
She opened the tube of KY and squirted for what seemed like forever into the top of my ass crack. I felt it run warm and gooey down my slit. First, one finger . . . two fingers . . . and both pass the knuckle. I loved it and grinded back on her fingers. I worked my feet back to rub her nylon covered legs. I couldn't get enough of her fingers . . .
Jessica stood up. "Turn around." I did as I was told. She looked down on me perched on glittering silver four inch heels. "Come closer baby," she said. And I inched my way over to her. She took her cock in her hand and rubbed it on cheeks and across my lips. Although I had never had any discomfort from our strap-on play, this was new. "Put your mouth on it." "Put me in your mouth." I hesitantly put my lips on her cock and felt the taste of the silicone in my mouth. She grabbed my head and forced me down on her rod. I felt it fill my mouth and ram the back of my throat. I was so hard and I felt my own precum leaking on my thigh. I grabbed her stocking covered thigh and felt the lace of her thigh hi tops as she fucked my mouth. I rubbed my hands up and down the smooth nylon and felt the back seem. I looked up at her sizeable tits as they swayed with her thrusts. She pulled the shaft in and out of my mouth. I knew that she couldn't "feel" anything but she looked to be enjoying it just the same. "You have such a velvet mouth cunt." Her dirty talk made my mouth water and the blow job got sloppier. Spit ran down the shaft and down my chin as I did my best to suck her dry.
She pulled out for the last time. She swung me back around to the couch. Dropping to her knees again and placing the head of her cock at my still wet asshole. I felt her enter and leave the head at the entrance of my ass. It felt too large and my ass felt completely full. She ran her hand up the shaft of my cock and gave my head a firm squeeze. My precum leaked onto her finger. She laughed.
"You little bitch." "Did enjoy that mouth fucking I gave you?" "I actually didn't think sucking cock would make you cum." "You are such a good whore. Tell me you are."
I didn't know what to say. I leaked even more as she smeared cum on lips. "I'm a good whore." "Take my ass, hard." I'd given up any inhibitions and any desire to hold back from this fucking.
"Swallow it." "Swallow your cum."
I did and she thrust hard into me. She gave a hard thrust and put all 8 inches in my ass. She held it there. And there I was. Naked with Jessica's strap on buried in my ass and my mouth coated with my own semen. I loved every minute and wanted more. I began rocking backing on her cock and she began fucking me hard. She grabbed me by my thong and pumped into me over, and over, and over again. I loved the feeling of her nylons on my bare legs. The dildo as it felt like it was splitting me in half. The submissive fucking on my knees in a dark garage. She leaned hard and leveraged all of herself into me. I felt her soft breasts and hard nipples as they swayed against my back.
I worked my gaping asshole back on her cock. Taking deep breaths to open wider and wider so that she could slide in and out of me with ease. But I wanted more. Her cock felt as if it were exploring every inch of my insides. A hard steel rod resting in the warm meat of my ass. I whimpered as she pulled herself out of me. Overwhelmed at my sadness at having her cock vacate my asshole.
She sat down and I climbed on top. Holding her cock and guiding it into my ass. Riding her was what I wanted and Jessica knew it. She grabbed my ass hard and pulled me over and over again on her cock. Two handfuls of my ass as she manipulated it around and down her cock. Harder than I wanted because it hurt, but I still wanted it harder. I loved crying out and moaning like a common whore. She moved me in circles and I felt now like a complete slut as she took complete control of my body's motion. "Give me that dick," I whispered, unable to contain my pleasure. I could feel the head of her cock as it went up and down my insides. She started to rub me and I was close to cuming.
And so was she. Her thrusts came harder and harder and I thought that my asshole would explode. The couch squeaked with our fucking. Her back almost stuck to the leather because of our sweat. She relaxed and leaned back. Sinking into the couch. She flipped her hair out of her face as she held me at my hips and ground into my increasingly raw ass. I felt her body begin to tense and I knew she was cuming. She gripped me tighter and cried out as she finished, thrusting the full length into me. I came, and I came hard. As I squirted on her chest and stomach she wiped it up with her finger and put in her mouth. She leaned down for a kiss. But as she had scooped up my semen she hadn't swallowed, and as we kissed she slowly spit a load of cum into my eager mouth. And our tongues wrapped around each other our mouths filled with my cum and saliva. What wasn't spilling out of the sides of my mouth I swallowed down hard.
"You've been a good slut tonight."
She slowly slipped out of stretched asshole and collapsed on the couch beside me. We returned to our traditional roles almost immediately. The only evidence remaining being my red lace thong and her cock. I crossed my legs, wanting to savor the last seconds of fem. But I was no longer the Sub, and she no longer the Dom.
She leaned over and kissed my shoulder. She smiled, and was beautiful. But I needed more.
I knew I couldn't be satisfied with her cock for much longer. I would need to be more submissive than her cock and my thong could provide. I needed to wear the stockings. I wanted to stand perched on top of the heels. I wanted to grab a cock between my hands and bury it deep in my throat. Cum smeared on my lips again, but this time mixed with my lip gloss. I wanted to ride a throbbing cock that Jessica could never provide. To feel that skin against my insides, holding my sphincter wide open. To feel that explosion deep inside and have an ass full of cum. To be bent over and feel a cream pie . . .
I wanted it all.