501 - A Night With Jenny

She seemed so at ease but then again she was on her home ground and I must admit as she sat herself down next to me on the little sofa I could feel the warmth of her body and it didn’t take long for the first glass of wine to disappear which seemed to calm us down..
Jenny: “Shall we have a top up, I certainly need it, I’d usually sit over there but we’re not on the bus now and this is much more comfortable, don’t you agree Frankie” she said softly as she reached forward to fill up the glasses and I did notice that she glanced down to see if I’d avoided any spillage however my chubby was perfectly noticeable, we raised our glasses..
Jenny: “Here’s to my knight in shining armour, thanks for getting me home safely, a perfect gentleman” she said turning towards me and clinking glasses..
Me: “Aww it was nothing Jen, it was nothing and you remind me so much of my mother, I’d hope that someone would do the same for her” I replied which opened up a whole new topic of conversation..

Jenny: “I see, and do you often make conversation with the older, more mature types on the bus or was it my striking good looks and blonde hair that attracted you.. or maybe it was my legs hehe.. I am a typical blonde you know” she said as we sat back glass in hand and she noticed me looking down at her legs which with her top riding up a bit gave me a slight glimpse of the white underwear she was wearing, I decided to keep the topic of conversation moving..
Me: “Well Jen, I rarely ride the bus to be honest but your striking beauty and blonde hair is definitely a plus point and you do have lovely eyes, yes I am attracted to the more mature woman and you can certainly blame my mother for that and I would certainly agree that your legs are rather nice too, sorry for staring” I replied as I felt something stirring in my pants and being a snug fit there was no way of hiding my pending arousal.. she seemed to appreciate my compliments even if she was fishing for them..

Jenny: “Aww you’re so sweet Frankie and of course I don’t mind you staring, it’s what guys do hehe.. I don’t get many compliments really as I seem to be stereotyped which is ok, I don’t mind.. blondes have more fun anyway so I’m told” she said as she widened her legs a bit pressing her thigh against mine..
Jenny: “Well I know for sure you weren’t attracted by my tits, unfortunately I wasn’t blessed in that area” she added as she pushed her small chest out in a rather seductive way, I couldn’t help but look..
Me: “Oh I don’t know.. it’s difficult to tell really” I replied with a cheeky grin as I surveyed her chest but then to prove the point she pulled her tee shirt outwards..
Jenny: “See.. I told you there’s nothing there” she said as I leant forward to get a perfect view of her small but perfectly shaped boobs, the good thing was she allowed me a rather long look down her top..
Me: “Hmm.. I see but you know Jen, personally I think they’re pretty good” I said winning another brownie point and enjoying the moment and feeling myself getting harder by the second..

Jenny: “Aww that’s nice Frankie” she said as she let go of her shirt and taking another gulp of her wine..
Me: “So what other imperfections do you think you have Jen, I’d be happy to offer my personal opinion” I asked seeing as we were in the mood and with the wine flowing all inhibitions were starting to fly out of the window.. she looked at me deep in thought like she was almost too scared to mention any other flaws, I waited patiently sipping my wine for her to answer..
Jenny: “Well Frankie, you might find this a bit weird but I think my arse is too big” she said with a giggle and if I’m honest most women have this problem, they all seem to want the perfect physique which unless you’re a catwalk model or something then we all have to play the hand we’re dealt..
Me: “Oh really, that’s an interesting comment Jen and not having seen your arse I find it hard to comment, maybe if you allow me to see it I’ll be able to give you a better answer” I said with a hopeful look on my face and I was only speaking the truth..
She looked at me as she contemplated my suggestion..
Jenny: “But if I show you Frankie you’ll think I’m a bit of a slapper won’t you” she said backing down a little and reaching forward for her drink which she finished off in one fail swoop.. I felt I needed to appease her a little..
Me: “Oh of course I won’t think that Jen and trust me, I have many imperfections myself too which I’d like your honest opinion on while we’re on this topic” I said which took her a little by surprise..
Jenny: “Oh really.. well in that case I guess I could show you.. and of course I’ll be happy to talk about yours too” she said feeling much better about it all..

She slowly stood up and turned her back on me as she moved right in front of me and then as she tentatively lifted up her shirt to expose her beautiful arse cheeks clad in a tiny white thong I could think of only perfection, yes her cheeks did stand out from the small of her back but in a delightful way and the tightness of her panties between her legs enhanced her lovely thigh gap, there was a moments silence as I surveyed her curvy cheeks seeing her thong string disappearing between her bulbous cheeks, I could tell she was getting impatient for me to comment..
Jenny: “Well, what do you think.. is it big or not.. come on mate, don’t keep me hanging” she said but I think that secretly she was enjoying her exposure..
Me: “Wow Jen, I see no problems with your arse at all, I like it so much I feel the urge to kiss it.. it’s perfect” I said excitedly which not only made her let out a sigh of relief but also made her giggle..
Jenny: “Kiss it.. Eww that sounds naughty.. but thanks for the kind words, they make me feel good.. I suppose a quick kiss won’t hurt” she added as she stood her ground waiting for that quick kiss I’d promised her, I reached out my arms and grabbed her hips extending my thumbs across her soft flesh just enough to ease her cheeks apart a little showing the thin string partially hiding her darkened hole and leant forward giving her a gentle kiss on each cheek and then quickly flicking my tongue into her exposed hole very briefly which did make her whole body shudder..
Jenny: “Oooh that’s naughty, you weren’t supposed to do that Frankie” she gasped making no attempt to move away.. making me wonder if I should do it again..
Me: “Oops my bad Jen.. I can only apologise or even do it again if you want” I said excitedly as I rubbed my thumbs across her cheeks widening her crack further.. she took a big intake of breath still holding her position as I pulled her a little more towards me..

I didn’t want to over do it and gave her just a few little licks just to plant the seed before she eased herself away..
Jenny: “Oooh you are naughty Frankie, so tell me what imperfections you have, I’d love to know” she asked as she poured more wine which I think was beginning to affect her, me too for that matter and while I was quite happy with my body I thought I would at least make something up just to give her peace of mind..
Me: “Well interestingly enough I too feel that my bottom is a little on the large side and from what I’ve seen in the school showers I think my penis is an underdeveloped..” I said embarrassingly and she immediately looked down at my bulging lap with a look of concern on her face, of course it was utter rubbish as I was quite happy with my bottom and my penis, is anything, was well over developed for a lad of my age but she did take my concerns seriously, typical blonde..
Jenny: “Oh really, that must play havoc with your self esteem and confidence.. would you mind if I take a look” she asked quite seriously as she took another gulp of wine preparing herself for the big reveal and because of her seriousness I decided to add another important point..
Me: “Oh and one more thing Jen, my sister thinks my penis tastes funny too, not sure if I should mention that to you though” I added as I stood up in front of her clearly showing my bulging pants.. the look of concern clearly increased as she admired my hidden boner with the wet patch seemingly growing.. I could see the excitement growing in her pretty little eyes..
Jenny: “I think it would be better if you took your shirt off too so I can get a better idea of your concerns, no need to be shy Frankie, I did see a naked man once before” she mumbled which was a surprising comment but being the exhibitionist that I am I was more than happy to oblige and quickly pulled my shirt off while her eyes scanned my upper body..

I reached down to the waistband of my sweats and undid the bow that fastened them, she took another inhale of breath in anticipation of what was about to happen and even bit her bottom lip as I slowly eased them down my hips taking care not to trap my boner inside and as more of myself became revealed her eyes widened and her eyebrows raised, she brought her hand up to cover her open mouth..
Jenny: “Oh my fucking god.. babe, there is absolutely nothing underdeveloped about that!!” she gasped as her eyes focused on the veiny shaft standing loud and proud with the tip covering my belly button.. my balls hanging down like to worn walnuts; I had to smile at her comment..
Me: “Really Jen, that’s so sweet of you to say.. you’re not just saying that because I complimented you are you?” I said as she looked closely at me with her hands on her lap fiddling nervously with the hem of her tee shirt.. she cleared her throat..
Jenny: “Oh god no, really Frankie, that’s is a wonderful specimen of male manhood.. do you think it’s possible for me to maybe touch it, I mean, just a little maybe.. Wow!!” she gasped in total disbelief that a lad of my age would’ve in possession of such a wonderful tool, how could I refuse such a sweet request..

Me: “I guess it’ll be alright Jen, we’re friends now aren’t we but be careful though, I’d hate to make a mess” I said humorously as I widened my stance for balance purposes and to allow for easier access, she nervously reached her hand forward and gently ran her fingertips lightly up and down the shaft which made my whole body tingle and eased herself to the edge of the sofa and reached out her other hand cupping my balls giving them a gentle squeeze, her fingers lightly encased my throbbing shaft and she eased the foreskin back to expose my somewhat wet and shiny head realising straight away what the wet stains were on my pants as a bit more precum oozed out the tip..
Jenny: “Wow Frankie, this is amazing.. now what was it your sister said.. did she say it tasted funny.. really!!” she said softly totally engrossed in my rock hard manhood..
Me: “Yeah, how weird is that right” I replied as I looked down at her twisting her head getting ever closer to me..

Jenny: “Well I’ve come this far and already dispelled your fears of underdevelopment so I guess I’d better have a quick taste, is that alright Frankie.. I don’t want you having that fear” she said as she pulled my dick down towards her face and gently licked around the head savouring the taste of my precum in her mouth..
She looked up at me unsure of her decision..
Jenny: “Well I’m no expert Frankie but it appears to taste ok to me, do you think she was mistaken or just winding you up.. or was it your cum that she didn’t like there of” she said showing a little concern for my problem.. I looked down at her..
Me: “Yeah Jen, it could’ve been that, maybe you could carry on for a bit and be certain” I suggested and she gave me a warm smile as she opened her legs to pull me closer..
Jenny: “Well I guess I could I suppose” she said with a hint of excitement in her voice as she bowed her head down taking my penis into her mouth…

With one hand on the base of my cock she pulled the other out from under my balls and placed it around my arse as she went to town on me, the warmth of her saliva running down my shaft with her head slowly bobbing up and down made my legs tremble, I put my hands on her head fiddling with her golden ponytail and started to gently thrust back and forth pushing me deeper into her mouth almost making her eyes pop out as I hit the tight spot of her throat and it was plain to see that my new blonde friend was getting into her task, her murmurs and mumblings echoing around the small room..
Me: “Oh yes, that’s really good Jen, keep going baby you’re doing great.. go on.. take it baby” I mumbled excitedly as we got into a sweet rhythm and I soon felt the pressure building up inside of me, she was very attentive and was certainly enjoying is as she continued to wank me into her mouth and with her other hand exploring my crack I was soon at the point of no return..

I held her head tightly as I didn’t want her to pull away and have to do it all again and soon felt my cock starting to pulsate shooting my load deep into her mouth, I needn’t have worried as she clasped her lips around my shaft forming a seal obviously not wanting to waste any of the goodness being fired down her throat, her mumbles of appreciation were pleasing to hear and she did a great job sucking every last drop out of me, my cock started to soften and I waited patiently for the verdict.. finally she pulled back and looked up licking her lips savouring the taste..
Jenny: “Mmm, was that good Frankie, personally I don’t think it tastes bad at all, I think it was nice and your sister is an idiot.. oh and from what I felt of your arse that is perfect too.. I don’t think you have anything to worry about, now where’s my wine” she said enthusiastically and as I stepped aside I had to look between her open legs seeing how wet she’d become in the crotch, her panties had almost become see through and a clear outline of her hairy labia could easily be seen and it was obvious that her little panties couldn’t hold her unkempt pubic mass, she leant forward to pick up her glass and with her shirt opening up I could clearly see down the front at her little boobies with rather stiff nipples, And I think Jenny had certainly enjoyed her experience..

I could see that the last glass of wine had tipped her over the edge as I saw her eyes glazing over and her head started to wobble a bit, I stood there still naked taking in the wonderful view between her legs..
Jenny: “I’m done.. I need my bed” she announced slightly slurring her words and I figured the best thing to do would be to help her get settled, it’s t
he least I could do and as I helped her to her feet she put her arm around my shoulder which helped hold her up..
Me: “Come on girl, let’s get you to bed” I said and to be honest I wasn’t feeling too sober either and it was quite comical as we both staggered to the bedroom..
Jenny: “Oooh now there’s an offer I can’t refuse.. I hope you’re not running home to mummy, your too drunk to drive hehe” she said giggling trying to focus her tired eyes and as we got to the bedroom which I will add wasn’t the tidiest bedroom I’d ever seen she sat herself on the edge of the bed struggling to keep her balance, at least I wasn’t rushing off having been given a drunken invitation to stay, plus I didn’t drive anyway..
I had no idea how she usually sleeps but figured if I was naked then so should she be, I raised her arms up which was a task in itself and finally managed to pull her tee shirt up and over her head however the whole manoeuvre unsteadied her balance and she fell backwards onto the bed with her legs hanging over the side but the sight of her semi naked body was a delight to see, her little boobies flattened but her nipples remained stiff and pert, now I had the job of getting her knickers off amidst the giggling fit that we both seemed to be suffering from..

I reached forward hooking my fingers into the tiny waistband and with her being a dead weight it wasn’t easy to pull them down but eventually amidst all the laughter I managed it and was so tempted at the sight of her somewhat hair bush with her glistening lips poking through the mass, it didn’t take long for my cock to start to stiffen and I wondered if she really knew what was going on..
Jenny: “Oooh Frankie, have you just undressed me, that’s so…” she mumbled before her speech cut out and her eyes closed.. I was in two minds what to do now, do I take a sneaky advantage or do I get her into bed and see what the sober morning brings, a very difficult dilemma I was in and being told by my father that a standing prick has no conscience I was seriously erring on the former, I mean.. what harm could it do..
I picked up her well soiled panties and took a deep sniff like that would help me make up my mind but the opportunity was there and I have to admit that the wetness and the rather pungent aroma did fill my head and enhance my erection, maybe just a little lick of those succulent lips wouldn’t hurt, she’d probably never know anyway, my mind was made up..

I got down on my knees pushing her legs a bit wider and as I leant forward I eased my hands up and under her thighs in order to squeeze her arse cheeks as my head neared its target, as my tongue swirled around her wet and puffy beef curtains I could see her growing little nubbin had come out to play and with my fingers searching into her crack I flicked my tongue across the swelling membrane, she jolted violently as she felt the tremors of my actions running through her body and even pushed her hips up forcing my face harder into her hairy groin..
Jenny: “What the fuck are you doing.. OMG that’s so fucking good” she said alarmed at my actions and as her hands came across I thought she was going to push me away but she just gripped onto my head applying enough pressure to keep me in place, she started to gyrate her hips rubbing her wetness all over my face and I could feel her now not so little clit starting to expand through the masses of light coloured pubic hair, I could feel her juices running down into her crack which was a welcome lubricant to allow my finger to push into her darkened back door which seemed to give her extra pleasure as I worked on her slightly deformed clitoris, she was soon shaking to a very intense orgasm and not even letting me up for air but as she squirted her juices all over my face it was a burden I was prepared to accept..

After her third orgasm in very quick succession something really weird happened, she released her grip on my head grabbing my hair and pulling it up, her head raised and her eyes opened like something out of a horror movie..
Jenny: “I think you should fuck me now” she said in a voice so strange it was like she’d been possessed, no laughter like before and a dead pan look which kinda scared me and I certainly wasn’t going to disobey such a strange and scary request.. I quickly pulled my finger out of her arse and grabbing the backs of her thighs I lifted her legs up as I climbed on the bed between them looking directly into her eyes which showed absolutely no emotion or excitement for what was about to happen..
With her being so wet I entered her very easily and quickly felt her cunt muscles taking a grip on me and her legs came around my back in some kind of leg lock forcing me in deeper, her eyes remained blank and as I got into my stride she pulled my head closer forcing our open mouths together, her tongue came out immediately and started to vigorously explore my mouth in some kind of frenzied way, as amazing as it was it was certainly freaky to say the least as I continued to pump away at her speeding myself up to try and finish quickly, it was my only chance of survival I felt…

She was so wet from her orgasms that I was actually finding it difficult but her kissing was rather passionate if in a robotic way, the way she searched my mouth and sucked on my tongue was quite exciting but I did wonder what was wrong with her and I could break away because of her leg lock around my back..
I increased the speed and my balls were banging against her arse cheeks and with the squelching sounds echoing around her little bedroom I had to use all my powers of concentration to just maintain an erection, this was all kinds of weird but I eventually did the business and filled her with my seed, it wasn’t an intense orgasm by any stretch of the imagination but it was an orgasm nonetheless and as she felt my seed pumping into her she finally released her grip..
I gave her a peck on the forehead as I finally slipped out of her and stood up looking down at her naked body wondering what the hell to do now, do I stay with this somewhat crazy and unpredictable woman to make sure she’s alright or do I cut and run, my heart was saying I should stay and ensure her safety because deep down I’m not a bad person but my head was saying get the fuck out of there because this woman was all kinds of crazy and it did go a long way to explaining the lack of relationships in her life and as I watched her distant eyes suddenly close I was still nowhere near making a decision..

To Be Continued…