I was 19. Living out of home for the first time following my dream career, 250km from my home town and loving life. One not so great aspect unfortunately was being a shiftworker, I didn’t have a lot of opportunity to go and meet women. Which was a bit of a shame because I had a voracious sexual appetite. I’d been with a few women/girls but I was pretty inexperienced. Looking back at it I was not a good shag and neither were the girls I was with to that point.
That changed the night Tess and I met. I had travelled back to my mums place to have beers with a few friends and was relatively fully loaded on ok said beers when I noticed two much older ladies than I standing next to me at the bar looking at me and giggling like school girls. Full of Dutch courage, I asked them if I could buy them a drink. To my surprise they agreed and went and sat back down laughing and looking at me with wry smiles on their face. I was fucking nervous as all shit and tried to keep it as cool as I can as I bought their beers over to the table and introduced myself.
The blonde, Rosie, was 43, married with 4 kids and a little rough around the edges. Sun tanned leathery skin and some badly faded tattoos on her breast plate and forearms but a great set of fake boobs on display. Her sister, Tess, was the polar opposite. About 5’7”, dark brunette, dressed in a black tank top with white cardigan and stupidly tight jeans on and great big black leather Fuck Me boots. I’ve always been an arse man and Tess definitely ticked that box. Single, a mum of 3, stupidly well spoken and smart. The chemistry was real, we reacted violently with each other in the best possible way. We couldn’t shut each other up.
We both ended up going outside for smoke and before I’d even taken my packet out of my back pocket Tess had grabbed my hips, pulled her towards me planted her tongue in my mouth. I’d never been with anyone who knew how to kiss like *this*. I squeezed her arse tightly as the kissing became more volatile and passionate. Tess rubbed the zipper of her jeans on my leg, moaning intermittently with each little movement we made together.
Alas, the pub was closing and both her and Rosie needed to get back to their kids being babysat. After the bouncer kicked us out, Tess and I exchanged numbers and started our texting marathons for the next two weeks when she had a child free weekend. Tess was classy as anything but a fucking nymphomaniac if I’ve ever seen one. She would often send closeups of her breasts and pussy, like from behind standing up with her feet shoulder width apart with with a rather large dildo firmly mounted in her cunt with the caption “I love to practice squeezing my vaginal muscles with this. It makes me cum so hard”. I wasn’t entirely sure what to say back, some 19 year old bullshit no doubt. But it must’ve been ok because 3 weeks later when my work roster allowed me to I was able to get her to myself for the weekend with no kids.
I drove to meet her in my home town (where she also lived) and as I walked in to the restaurant and saw her I’ll never forget the look. I was nervous as shit but so was she, so much so that as we locked eyes I could feel her heart skip in tandem with mine. There was a huge hug like two lovers who’d been separated for years. much desire and lust evidently existed between us. It was beautiful looking back 12 years later to see how perfect that moment was for two people who were so different yet so well suited. We talked about her kids, her relationship breakdown, politics, history, life goals and fuck knows how many other things.
But the look in her striking light brown eyes as more and more wine was consumed told me the moment to leave was presently upon us. We paid the bill and got a taxi the 20 minutes to her place. No sooner had we jumped in the cab we started the same brand of passionate kissing we had 3 weeks prior. I was behind the driver and Tess was in the middle, she unzipped my rock hard penis from its cotton cocoon of my underwear and just looked at it with her left index finger and thumb wrapped around the base of it and whispered in my ear “Oh my god Robert, you’re beautiful”. For a 19 year old to hear that from a 37 year old who’d always been worried about size (4 1/2” erect) that did my confidence an immeasurable amount of good. She then without pausing enveloped that entire 4 1/2” of 19 year old penis in her mouth. She mainly focused on my glans with an evident knowledge of how to make a man blow. My first proper head job was an absolute cracker. I tried unzipping Tess’s tight jeans but she protested telling me “the first thing to touch me is going to be your tongue”. I wanted to chow down on her there and then in the cab.
I could feel myself getting close to orgasm, so I gently pushed her head away from me. Although disappointed I couldn’t cum down this beautiful woman’s throat, by this time we were at her place. “Don’t fuck this up Rob” I kept saying to myself. We walked down the garden steps, hand in hand. My cock was still raging hard, the butterflies were flying in my stomach, my mouth dry and I couldn’t be more excited. This was going to be fucking good.
Tess let me in first, her house was stone floor tiled, open living area with a huge bookcase of different literature. I walked a few steps in and she shut the door behind me. I turned around and we stood there in the dim lights looking at each other. She walked over to me and held both my hands. Her next words somewhat surprised me “I need you to be very kind to me, I’ve had 2 Caesarians and my last pregnancy gave me bad stretch marks”. I didn’t say a word and just smiled, kissed her and held her close.
She led me in to her room with her huge bed that felt like the size of a football field. Tess and I slowly undressed each other on the left hand side of her bed until we were naked. She was the most beautiful woman I’d ever laid eyes on. Her C cup breasts were pert with lightly coloured pink nipples and her bum was a perfect “mum bum” not taught and trimmed but quite large and wonderful to lay my hands all over.
I felt the two distinct horizontal scars from her births as I caressed her belly, which for 3 kids was quite flat with some ever so faint stretch marks down either side. This was a real woman, she had battle scars of life and I was in love with her body. She nervously quavered with her breathing. I must’ve been doing the same but don’t recall it.
The glans of my cock and some of the top of the shaft had been touching her pussy whilst this was happening. As a pulled away slightly to allow her to lie down on the bed, it was glistening with wetness. Tess lay down on the side of the bed with her legs at the knees hanging perpendicular over the side, her legs wide open with her absolutely stunning labia staring at me. As I got down to kiss the inside of her thighs and tease her she quipped again “please be kind to my love”. I ignored her as I lay my tongue on the outer edges of her labia, feeling around for her clit. Although relatively inexperienced I was pretty competent at cunnilingus for my age.
Tess moaned at me “put your tongue inside me love” and I buried my tongue as deep inside her grool soaked vagina as I could, my face being covered in it in the process. She’d obviously shaved that afternoon, a new experience for me at the time. She was just fucking amazing. I knew though I needed to make her climax, so I went back to burying my tongue in to her clit. It was slow, passionate oral. Deliberate swirls around her enforced clitoris. Her moans were deep, drawn out and not particularly loud. Tess came very quickly, and squeezed my head between her thighs that hard that I couldn’t breathe.
I stuck my tongue back inside to taste her and it was blissful. Her hot girl cum cut through my saliva like nothing I’d ever felt before. She told me beforehand she loves to taste herself post orgasm so I preserved as much as I could on my tongue and kissed her. Hottest thing ever to see how turned on she got. I couldn’t stand it any longer, I reached down to my penis and manoeuvred it inside her.
As I moved my cock back and forth out of her, making deep deliberate strokes as if I was reaching for her womb, she moved her legs back to get it in deeper and she and I moaned together. She not too soon after she pulled out, lay me on my back and climbed on top of me, where like a machine gun she ground our public bones together straddling me. I held her breasts as tight as I could as she came again, collapsing in a heap on top of me.
I had to go to the toilet by this stage thanks to the copious amounts of alcohol so I tell her my plan and that I’ll have a quick shower so we can continue. Plus I was about to blow my load and I wanted it to last a bit longer.
After the quickest leak/shower of my life I come back out to her with that dildo I mentioned previously quite convincingly jammed inside her. I tell Tess to leave it in and get on all fours. She does as I bury my tongue into her ass and that sent her wild. She held the dildo deep inside her and let out this long, gutturally loud scream of pleasure as she orgasmed. Taking her dildo out covered in glistening girl cum she begged me to fuck her from behind, which I did for what felt like ages. I didn’t want this to end but the feeling in my glans and prostate told me it was close.
She asked if I was close and I said I was. Knowing she was still very capable of becoming pregnant and neither of us needed that, Tess lay on her back again and said “let’s fuck nice and slow till you’re ready then cum on my chest so I can watch it”.
I did so accordingly, however between watching her breasts jiggle as I slowly but forcefully made love to her, watching my cock slide in and out of her with her legs over my shoulders and and her facial expressions of pleasure it didn’t take long. I pulled out and with my right hand made three slow strokes of my cock and unloaded on to Tess’s breasts with what was (and still is to this day) the thickest and most forcefully expelled load of cum I’ve ever had. Tess moaned with me as she held my balls, her left index finger feeling my prostate contract incessantly.
I still had man juice leaking out of me as she pulled me towards her and we kissed, my cum getting tangled in my chest hair without cleaning anything up we fell asleep where we lay. Tomorrow morning is part 2….
Source: reddit.com/r/eroticliterature/comments/bxr3ex/mf_tess_the_woman_who_taught_me_what_sex_is_all
lovely read… very hot!