I lost my virginity when I was 18 to my Mom’s friend Jill, whose family lived behind us on the same block. Over the winter Jill’s husband Dave moved out and by spring the divorce was final. To help her out Mom offered me up to help with any chores she needed done and to take care of her yard over the summer.
Saturday morning of Memorial Day Weekend I was at Jill’s mowing, trimming and taking care of any other yard work she needed done. I’d finished mowing and was in the garage cleaning the equipement and putting things away when Jill looked out and asked me to come inside before I leave. So when I finished up in the garage walked into the house, shirtless and sweaty and called out to her as I headed into the kitchen.
She came in, got a Gatorade out of the fridge and handed it to me. Leaning back against the counter she asked how I was doing, how everything was going for me. Complimented me on how great the yard looked, how great everything looked with me around. I started to sense that she was moving from being nice to flirting with me, or maybe it was me hoping she was. Then Jill asked “do you have a girlfriend Jake,” I smiled nervously “no, noone yet”. She cocked her head grinning at me and I shrugged, “a hot young man like you, surely there’s at least one girl out there willing to give it up to you anytime you want it.” I grinned shaking my head at her, ‘”nope, no one”. I was getting nervous and I could feel myself blushing, scared as fuck and totally lost not knowing what to say or do.
That’s when she walked up to me and gently slid her fingers over my chest and stomach, “not one girl, so have you ever?” she asked. Now I was lost, not sure what to do, embarrassed and nervous I muttered “no, never”. She looked up into my eyes and I could feel her loosen my belt and open my jeans. Getting on her knees she kissed my stomach then slid her hands into my jeans and pushed them down, “Dave never went comando, but I think it’s hot.” She got my cock out and I felt her tongue run from the head to the base, “you’ve got a nicer cock than he does too.” I could feel myself trembling, a little self conscious as my cock began to swell for her, and when she took each of my balls in her mouth my breath caught. She giggled “nice” and then the warmth of her mouth surrounded my cock as she started sucking and licking my cock. I was rock hard now and I put a hand on her head, running my fingers through her hair. Which one hand roaming my stomach and chest she sucking my cock nice and steady, occasionally licking my balls. It didn’t long for my load to start building up, my breathing quickened, panting and I took a hold of her head and started to fuck her mouth. But she pushed against me and took back control, eyes closed, head lolled back, I held onto the counter tight, shaking, panting and whimpering, groaning as I blew my load down her throat. I looked down at her catching my breath, “fuck” was all I could manage to say as I drained the last of my load.
She stood up and put a hand behind my neck and I tasted my cum on her kiss. Not sure what to do now or what to say, other than get my still swollen cock back into my jeans. Jill asked me if I had any plans for my Saturday night and I was fumbling for an answer when she put her hand on my chest. “I’ll text you later, you jump the fence and we’ll figure it out together.” All I could do was a nervous smile and a shakey “sure thing.”
I was in another World as I made it made my wath through her back yard and back home. My cock still stiff, still horny and my mind was fucked. Jill was 41, my Mom’s best friend, what if someone finds out? What’s going to happen now? What about tonight? It’s never going to be the same as it was. I showered, grabbed some lunch then spent the afternoon over thinking just about everything I could think of. After dinner Mom and Dad were heading out for the night so I helped clean up after dinner then chilled in my room, anxiously waiting and wondering if Jill would text.
When my phone dinged my heart hit my throat, -you wanna come over at 8?’ Taking a deep shaky breath I replied -‘sure, 8 works great.’ I felt the anxiety build and her next text was -‘back door is open just come on in.’ I grabbed a hot shower, shaved, slipped on a pair of athletic shorts, checked my fit, hair just right, cologne, and nervous as fuck. I tried my best to chill and when 5 till finally got here, I grabbed a muscle shirt and headed out the back door and jumped the fence. My heart was pounding as I opened the door, announcing myself as I kicked off my shoes. Jill called out and I found her in the kitchen, white lace panties and bra with a glass of wine. My mouth immediately went dry as soon as we started talking and I got a Gatorade from the fridge. I could tell from the small talk Jill was a bit nervous and anxious too, but clearly not as bad as I was as I stood there wondering if she could see me shaking.
When she finally led me upstairs to her she’d definiely set the scene. The lights were dimmed, bed freshy made with a sheet and pillows, scented candles and the flat screen TV on the wall was playing muted porn. I set my drink on the dresser and nervousely stripped down when she disappeared into the bathroom. When she came out of the bathroom I stood there naked, feeling like I was presenting myself to her as she walked up to me. I took a hold of her waist and her hands slid down the small of my back to my ass and pulled us together and kissing my neck. For the first time I realized how small and petite she was, maybe 5′-7 and 120 to my 5′-9 and 155. We started kissing and I managed to unsnap the front of her bra, slid the straps off of her shoulders exposing her firm perky tits. I held her and leaned down and began kissing and sucking her tits as she sighed and held my head to her, running her fingers through my hair. I kneeled in front of her, kissed her stomach and gently sliding her panties down and helping them to the floor and she held my shoulder supporting herself as she stepped out of them. My hands softly ran up her legs and took her ass in my hands as I leaned in and kissed right above her bush, only to hear a soft “not yet”.
I stood up and she took my hand and I followed her onto the bed and laid back in front of me, spreading her legs and pulling me to her. I laid in her arms and laced my fingers over her head and she caressed and held my back as we kissed and made out. I began making my way down her body, kissing her neck, her tits and stomach to her pussy. Laying on my stomach between her legs I kissed her thighs before licking and sucking her pussy and her soft moans made me want to explore and taste her more. Licking and sucking her lips, she reached down and spread her lips to expose her clit, pink and swollen and I locked on. I sucked and caressed it with my tounge while my fingers massaged and probed her, moaned and squeeled she creamed and relaxed with a sigh.
She took my face in her hands and I got up, I sat back on my ankles, her legs wide open, holding her thigh I teased her pussy with the head of my cock, caressing and pushing agianst her. I pushed the head of my cock into her then leaned over her, sighing “oh fuck” as my cock sank into her, smooth and tight as her heat flowed into me. Wrapping her arms around me, holding me tight, kissing and sucking my neck, I started to move inside her, slow and steady, afraid I’d cum too soon. As we got going it was like our bodies were in sync, the way she moved with me and against me, her rythem and reactions to my body. Getting close I picked up the pace, my balls were tightening, the sensation in my cock was intensifying, I felt like I was on the edge, now afraid I wouldn’t be able to bust. Whimpering, trembling, sweating dripping off of me, panting I let out a moan, I felt like I’d lost control of my body when I felt my load shoot into her, like my cock exploded.
She held me in her arms and we kissed, until the spasms stopped and I’d finished draining my load into her. I rolled off her onto my back catching my breath and she roll on top of me. I wrapped my arms around her and held her tight as she kissed and nuzzled my neck and whispered “very nice”. I giggled and kissed the top of her head, “shit, I was awkward, clumsy and nervous as fuck.” We laid there together for a while, it seemed like it was getting late, I kissed her on the head, “I should probably be getting home before Mom and Dad get home.” She rolled off of me giggling and patting my stomach and was going to walk me out, but I told her to stay in bed and I locked the door on my way out.
