In the fall semester of my junior year of college, I had a short 3 month affair with Jill. Jill was a basketball player for the neighboring university. She was a foot taller than I and absolutely stunning. Blonde wavy hair, big blue eyes and beautifully athletic body. While I was her first woman lover, she was definitely adventurous and very dominant. Most of our play was led by her desires and things she wanted to try. Some of the hottest lady sex I’ve ever had was with Jill. The story I’m about to share is one of the few times that our play focused more on her.
Jill had come over on a Saturday night after practice. She came with a bag of food for snacks and a rented movie from Blockbuster. Settling onto the couch, she laid out snacks and some beers on my trunk which doubled as my coffee table in my dorm room. We munched while catching up about our weeks, not really watching the movie. Eventually, I started to pack up some of her snacks and went to put them back in the bag she brought. At the bottom of the bag was a very large cucumber. I smirked to myself because Jill was very adventurous and loved fucking me with toys in both my pussy and ass. I pulled the vegetable out, holding it in my small hand. That thing was HUGE. It was at least 10″ long and 2″ thick. There was NO way I was taking that thing.
I held it up to Jill with a questioning look; she laughed hard replying, “No babe, that’s not for you. I want you to fuck me with it.” Whew was my first thought followed quickly by surprise. Jill generally didn’t allow me to use my toys on her. They were smaller and she preferred me to eat her pussy and ass or finger fuck her. I was excited at this new twist.
Jill pulled me onto her lap and we started to kiss. She was a very assertive lover. The mix of femininity and dominance was intoxicating. I straddled her legs and pulled my shirt off allowing my ample tits to drop into her face. She latched on immediately, suckling my nipples into hard points. I pulled her face back up to kiss again, pushing my tongue into her mouth. She grabbed my ass pulling me to grind down on her. We continued to kiss and caress for a long time before I climbed off of her and pulled her to my bed.
We both quickly undressed and slid under the covers together, the cucumber laying on the nightstand next to us. I kissed her again and then asked what she wanted me to do to her. “Fuck my ass with it.” Jill whispered. Holy. Fuck. I thought. I asked her if she was sure and she nodded her head firmly.
Pulling away from her, I told her to get on all fours and put that beautiful tight ass up in the air. Settling myself between her calves, I dug in with my mouth and tongue. I started eating her pussy, slowly at first. Teasing her open, licking her lips and sucking them into my mouth. She was getting so wet as I ate her. I sucked her clit and tongue fucked her over and over causing her to cum for me just from that. Jill was so fucking beautiful when she orgasmed. Her body would tremble and shake, her long legs would get tense. It was amazing. I moved my way up to her ass, and began to eat it. Her little hole was so tight and puckered. I lapped at it, poking my tongue inside to loosen her up for that giant cuke. When she was very wet and soft, I asked her if she was ready and she nodded yes from the pillow.
I grabbed the vegetable from the nightstand, I couldn’t get my hand around the middle. Good god was all I could think. I asked if she had washed it and she said yes. I wrapped my lips around it to get it slick and then pressed the tip to her ass. I had to push firmly for her to open to it. I was seriously frightened I would hurt her and I said so. But she said, “keep going, it’s fine.” I pushed a bit more, watching with a sick fascination as her asshole spread more to accommodate the thickness. She moaned loudly into the pillow as I worked it into her. Pushing in a bit and then sliding it out. I was spitting on it to keep it lubricated, along with her asshole.
Once I had worked about 2″ into her, I let go of the hip I had been holding and reached under to rub her clit. Jill cried out when I found that little button and said to keep fucking her. I held onto the cucumber and pushed more. She was so wet now, along with the cucumber. As I pushed, I felt her push back as well and suddenly, thing slid in another 4″ or so. Jill screamed into my pillow, scaring the shit out of me. I went to pull it out and she whipped around and quickly told me, “NO”! “Leave it.”
I held very still, giving her time to adjust to the intrusion. She breathed slowly and deeply, relaxing her body and mind. I planted soft gentle kisses on her ass, and lightly used my nails to rake over her thighs.
Jill began to rock slowly, her body moving gently against the cucumber I was holding still. I watched as her ass would stretch open at the thicker parts and shrink smaller as she pulled away. Her movement was slow to start but gradually built to longer, deeper strokes as she fucked herself on it. Fuck it was hot. Gently, I spun around and lay under her so I could lap her pussy as she fucked the vegetable. I licked her slowly and gently, occasionally glancing up to see her face.
Jill was in a trance is the only was I can describe it. Her body was there but her mind was gone as she fucked it and I ate her. Her pussy was drenching, dripping into my face. I slid my tongue up and down as she rode me face and that cucumber. I began to slide my tongue into her cunt, slowly fucking her. I could feel her body trembling, I knew she would cum soon. I moved to her clit and started to gently suck her. I could feel her movement on that cucumber. She was taking more and more of it with each stroke. I dug my nails into the last two inches of it, holding it steady as she stretched her ass around it.
Jill began to moan loudly and I knew her orgasm was coming. When it hit, her body convulsed, her pussy flooded my face and mouth, her ass clinched down so tight most of the cucumber pushed out. She cried out into the pillow, her body trembling above mine. I stopped sucking and fucking her, allowing her to ride it out. She collapsed on top of me, the cucumber sliding out. I dropped it to the floor and then started to stroke her body as she rolled off of me and to her side. I moved up the bed to hold her, pulling a blanket over us. We slept that way that night, just snuggled together. I loved pleasing her. She rarely allowed herself to let go that way and I adored when she did.
Source: reddit.com/r/gonewildstories/comments/y9vmzm/mf_a_cucumber_ass_fucking
Good god the only thing you used for lube was spit!!
Really hot story though.