***It's been a while since I’ve written one of these stories and I kind of rushed this one so please bare with me. However contructive criticism and PMs are very welcome :) Cheers
Jenny could tell by the way that I moaned deeply into the pillow and pushed my ass further back that I liked having my asshole penetrated by her tongue.
Never before had a girl done this kind of thing to me and I'll admit, I was sceptical at first as to whether or not I’d like it but, now I was in heaven...
I was supporting myself with one hand and my knees as my head pressed into a pillow, my other hand was wrapped firmly around my 5 inch cock, jerking it in rhythm with Jenny's soft tongue.
Just a quick back-story, Jenny and I were both 18 and soon to graduate high school. We never really talked until grade 12 physics class when we sat beside each other and helped each other with the homework or I borrowed a pen whenever I forgot mine in another class.
Jenny had invited me over to study. And study we did for about 20 minutes, then ... we started kissing, my clothes came off and next thing I know I’m bent over on her bed and this cute blond is pulling my ass cheeks apart and licking my asshole; expertly, I might add...
"Jesus, Jenny that feels so good!"
"One thing you'll learn about me James; I love boy's assholes" she said in between licks
Without warning she stopped. "Hey James, I’m kind of into...being in control...would you mind if I used these?" From between the bed and the wall she pulled out 2 pairs of red furry handcuffs.
"ummmm, well I’ve never had a girl in charge before" I said looking over my shoulder.
Jenny looked into my eyes and pulled her shirt over her head, her beautiful C cup tits bounced out from under her shirt. She was wearing a stunning black lace bra that covered barely enough to be even called a bra...
"Now listen, young man..." Jenny said as she massaged her nipples with her palms through her bra "...you let me use these and I’ll lose these" she said raising the handcuffs with one hand and undoing the button of her jeans.
"Oh my god yes, do what you want" I was hypnotized! I would have emptied my bank account for this girl at this point!
As I motioned to roll over she stopped me with her hand. "no no, James, stay bent over like that". She used one handcuff to attach my hand to the corner of her bed and the other to attach my other hand to the other corner. Now that my hands were too spread out to support myself I was completely flat on the bed and feeling rather more vulnerable than was normal to me...
"Babe, how will you be able to get to my cock if I can't roll over?"
"To be honest James, it's not your penis I want right now..." she spread my ass cheeks and continued to lick, this time more aggressively than last.
My eyes rolled to the back of my head as I drifted off into another world.
For 15 minutes I was completely lost in this new sensation when out of nowhere I felt a chillingly cold substance being rubbed around the edge of my asshole. I flinched violently at the shock.
"What the hell was that" I managed trying to look over my shoulder.
"Lube, you'll want it" Jenny said
"What are you going to..." I didn't finish my sentence before a finger was pushed all the way into my virgin asshole. "fuckk Jenny!" I moaned as I was overcome by fear, then confusion, then pure ecstasy...
Jenny slowly slid her finger in and out of my ass for the next little bit, at some point reapplying more lube and transitioning to two fingers moving in and out...
"Do you want something else now James?" Jenny said as she slowly removed her fingers from me.
"Yes please" I smiled as I looked over my shoulder at her.
She unlocked one of the handcuffs and allowed me to roll over before she reattached the handcuff to the bed post. Locking me onto my back now.
Jenny smiled, took off her bra and took my 5 inch dick into her mouth. Working her tongue around the entire shaft and head as her hands massaged my balls.
I moaned deeply as she worked my cock over with more vigour. She moaned as well as she took all of me down her throat. My legs were spreading as I was pushing my hips up to meet her sweet mouth as she went down on me.
She slowly reinserted her index finger into my tight asshole as every muscle in my body tensed up and I exploded. Rope after rope of cum spraying into her mouth.
After a couple seconds my muscles relaxed and I came back out of that stupor that always follows a good finish. Jenny rose up my body opened her mouth to show me a mouthful of me. Then closed her mouth and eyes and swallowed deeply.
She then leaned down and kissed me. Sharing with me for the first time the taste of my cum off her tongue. I was a little weirded out, but just for a second before I realized that it wasn't so bad and if she was going to swallow me, I could at least taste myself. And what could I do anyways. I was restrained pretty well...
"What do you want now?" Jenny cooed as she slid forward even more so that she was now seated on my chest.
"I want your pants off" I said, wanting to see her pussy and at the same time hoping that I could get myself hard again real soon...
"Are you sure you pant my pants off? I’m not wearing any underwear..."
Jenny knew what she was doing to me and she loved it. More than I'd ever know...
She got up off me and walked to her dresser and pulled out what looked like a blind fold and pair of full butted panties.
"I hope you're not going to wear those panties..."
"Oh neither of these are for me baby" Jenny said with a mischievous smile.
She sauntered over and put the blindfold around my head. When I protested she reassured me that it was all going to be worth it.
With my blindfold on my other senses went into over drive. I heard her take off her pants, I felt her get onto the bed, again between my legs, I felt her tits brush against my chest as she stuffed her panties into my mouth and when she removed the blindfold the first thing I saw was her beautiful smile, then her gorgeous tits, then her hour glass shaped waist, then her cock.
I was in utter shock! I started to yell but with her panties stuffed deeply into my mouth it all just came out in muffled cries.
She slapped my face, real hard. My ears were ringing and my screaming was replaced by silence. She had my full attention.
"Baby, I know this is a shock to you. And I know that you may not agree to this, but it's going to happen. You may not think so, but you're going to enjoy it a lot. It's quite a bit bigger than yours (and at at least 7 inches, it was) but soon you'll be moaning in delight" and she leaned down and kissed my gagged mouth and whispered "I promise".
The look on my face was no doubt terror as she brought out the lube again and this time was applying it generously to her rock hard cock. I wasn't gay...but I wasn't homophobic...and when she was fingering me it did feel amazing...then again two fingers was nothing compared to this...
"Take a deep breath James, this might hurt at first"
She pulled my legs up over her shoulders and aligned herself with my asshole. I screamed and squeezed my eyes shut as I felt the head of her cock slip into my butt. I felt the rim of her circumcised head slip into my asshole and more stretching as her smooth cock was pushed deeper and deeper into me...
My screams turned into gasps for air as I thought that her cock was never going to stop penetrating me... "A couple more inches, my little boy" Jenny breathed. After what seemed like hours (but was actually only a few seconds) she stopped pushing in. Leaned forward, pulled her panties out of my mouth and kissed me deeply and more passionately than anyone has ever kissed me. Now more than ever I was aware of not only her soft lips, delicious tasting tongue and her sweet smelling perfume but now I was feeling the distinct throbbing of her dick nestled deep between my butt-cheeks...