It’s 1130 on a Friday night, I’m at the pub with my friends who I played football with. Drunk as an absolute skunk. I stood at the bar with 3 schooners of beer jammed in to my hands, I turn to my left and nearly spill the leading glass all down Tess’s front. Instead of going off at me, this beautiful woman laughed at me and helped me to carry my drinks back to my table. I offer in return to get her one. She’s older than me, much older. But I was young dumb and definitely full of cum and thought I had nothing to lose. To my absolute surprise she said sure and asked for a glass of Sauv Blanc.
Tess and her sister Rosie come over to our table and join us. I sit opposite to Tess in the booth. We introduce ourselves with a handshake, and at that moment the sparks started flying. Her piercing brown eyes lit up, as mine more than likely did too. She was my exact height, five feet and six inches, a beautifully trim body for 3 kids, shoulder length short hair, B cup breasts and a slight English accent from a stint living there.
We couldn’t stop talking, it was like a match made in heaven. I got up to go to the bathroom and as I exited the loo she was standing there waiting. I froze with fear and excitement, she grabbed my arm and pulled herself towards me and began to entwine our mouths and bodies together for what seemed like an eternity. This was rudely interrupted by the bartender telling us to “fuck off you two the pubs shut”. And sadly, her sister and her had to go back to Tess’s place and relieve the babysitter looking after her 3 kids and her sisters 2 kids. Numbers were exchanged with much more kissing and groping before she jumped in to a cab and I caught the last train back to my mums house.
The next two weeks was torture waiting for our next meeting, but fuck was it worth it. We met up again on a Friday night, Tess was stunning. The tightest jeans I’d ever seen, a cleavage exposing green top and fuck me boots. We had dinner, and I asked her if we should catch a cab to her place. Tess protested cunningly from behind her glass of wine with a wry smile “It will be so much better if we tease each other for a bit more, won’t it?” Holy fuck this woman is a Goddess.
Tease she did. We got drunk and talked so much. The level that we were on with each other for such a big age gap was out of this world. You could cut the sexual tension with a knife, it was going to be so good. Eventually neither of us could stand it much more. In the smoking area, we started to kiss again as she straddled my thigh and used the zip from her jeans to grind her clit. My penis was the hardest It had ever been. I pulled away, grabbed her hand and lead her to the taxi rank to get back to her place. She said to me “make sure you sit behind the driver”. I duly did so, and she unzipped my fly and placed my stupidly hard cock in her left hand, whispering to me “My god you’re beautiful” before giving me to this day the most sensual and incredible head job I’ve ever had. I pulled her head away softly just before I was about to cum. At that point of my life no one had been able to make me cum from head.
I went to unzip her fly to reciprocate the favour, but again she stopped me and teased me saying “I want your tongue to be the first thing that touches it”. Thankfully we were by that point only 5 minutes from her place. We walked down the dimly lit path hand in hand. When we got inside there was no instant stripping of clothes like the movies, we walked to the entrance of her bedroom door turned the light on and stared deeply at each other. “What the fuck was happening?” I thought to myself. It was an inexplicably palpable moment, here we were about to spend the next several hours exploring each other’s bodies, finally. After weeks of sexting and photo swapping, phone conversations etc.
Tess pulled my T shirt of slowly, dumping it on the ground and running her hands through my chest hair. She breathed heavily, I could see her bottom lip trembling as she exhaled. I reached over and slowly unbuttoned her jeans and pulled her French cut purple lace undies down with them in one slow downward movement. As I rose up from my knees she said “My body isn’t what it used to be after 3 kids, please be kind”. There was definitely no need to worry about that, she was beautiful. I pulled her shirt up leaving only her bra on as she unbuttoned my jeans, leaving me exposed in all my nudity with my ragingly hard cock. I put my hands on her stomach, showing the scars of 2 Caesarean sections and stretch marks. “You hate them don’t you?” She quivered. “Nothing could be further from the truth” I replied, and that was the truth indeed. Tess was beautiful. I ran my hands all over this wonderful woman’s body, her inner thighs, he slim little arse and after she took her bra off finally her wonderfully dark and pointy nipples. Her breasts were such pert and rounded ones for a mum of 3.
I laid her down on the bed in front of me, spread her legs apart, knelt on the floor and wrapped my tongue around her absolutely soaking and engorged labia. I’d never seen a vagina with so much grool on it as a 19 year old. It tasted so warm, I was in heaven. Tess let out these little sharp gasps of pleasure as I sucked on her clit, interspersed with these amazing, deep groans of pleasure. It sounded like she was in labour, if that helps to imagine with sound. I didn’t get the chance to make her cum before she grabbed my hair and pulled me up towards her mouth and kissed me with every inch of passion she could muster.
I then didn’t fuck about, and slid my 19 year old cock in to her tight and soaking 37 year old slit. I nearly blew my load there and then, she saw this and asked “if you blow can you go again?” “Of course I can babe” was my response. “Good, let’s fuck till you cum then you can shoot it down my throat” just hearing that nearly finished me. We did missionary for about 10 minutes until I could take it anymore, and I pulled out and straddled her face, with Tess taking my cum by frenetically rubbing my cock as I cried out in pleasure.
We got up after she swallowed and got in to the shower. My dick still ragingly hard, we lathered each other and teased, kissed and spoke dirty. She asked if I was ready to go again after I’d got out and dried myself off, noting my still hard penis. Tess ordered me to lie down on the bed, she clambered on to me and started grinding like a woman possessed. She ordered me to thrust my hips hard towards her pelvic bone as she leant back and rested her hands on my thighs and went nuts until she came. I’d never felt a woman cum around my penis before, and I was probably like a deer in the headlights when she did but I’ve never felt the clenching screaming like that before, and to top it off as she climbed off not only could I see her creamy girl cum running down the front of my cock, she sat on my face for me to experience the taste of her. Never had I been so ravishingly horny.
I was close to coming again, so I asked to fuck her from behind and Tess told me to play with her arsehole while I was at it. For the next 10-15 minutes I fucked her slow, I fucked her hard “your balls are slapping my clit!” She screamed in what sounded like agony to a 19 year old naive lad. All the while I had my thumb in and out of her wonderfully tight arsehole. “I can’t get pregnant again babe, cum on my chest!” As soon as she said that I pulled out, rolled her over on to her back and she finished me off, dumping what little I had left in my balls on to her nipples. We talked and embraces until just before the sun came up and went for another round in the morning and afternoon, but that can wait for next time.
Tess taught me what it was like to make screeching, hot, intimate love. She showed me how sex should be: wet, fast, hot, messy and full of passion. She was my first REAL sexual partner and I still wish we’d ended up together. As above though, our heartbreak will have to wait till next time.
Source: reddit.com/r/gonewildstories/comments/9jsu7t/mf_my_first_real_sex_she_was_37_i_was_19