Sophia Teaches Me How to Love a Woman

Before I begin to tell the story, this is my first ever story on Literotica. I welcome any feedback as long as it is constructive and will make me a better writer. This is totally a work of fiction but it is something that I wanted to happen when I was in my twenties but it never did.

I hope you enjoy my story.

Chapter 1

My name is Jack, I am 20 years old, and I have never been sporty so I don't turn heads like some guys do. As a result I have not had much attention from women and have only ever had a quick feel over clothes before.

I still live with my mum and spend most of my time in my room where I have a television and a laptop so I have everything I need really. I like the way that if I get disturbed unexpectedly I can just shut the laptop or change the channel and I don't get busted. I love to look at porn on my laptop and for a while now I have started to look more and more at MILF sites. There is something about a more mature woman that gets me going and I end up masturbating to the images I see. I particularly like the woman with normal panties on and a full bush of pubes. Totally shaved to me is wrong on a MILF but that is just my taste.

I have a particular site that I go on and I am in heaven every time I visit it. It is full of women in conservative dress, not overly made up and looking hot. The photosets start with them fully dressed and end up with them playing with themselves and naked by the last one. As soon as their panties come into view I am as hard as a rock and I start to play with myself until I come into a tissue. I have dreams about the women that I see on the site, they tease me by lifting their skirts up, exposing a bit of thigh, opening their legs a bit too much so I see up between them but when I ask for more they say no and just keep teasing me until I wake up with a hard on. I grab a towel to hide my erection in case I meet my mum and rush to the bathroom. Once in the shower I think about my dreams and what I have seen on the laptop and start to play with myself, slowly at first until I can feel the start of my orgasm and then I speed up until I come on the floor in the shower and watch it get washed away down the plug hole so there is no evidence of what I have done.

I decided one night to go to the local bar for a drink and to watch the football. My team were playing and so I thought it would be good to do. I should have stayed at home though because my team were useless and at half time we were 3 goals down and didn't look like we were going to score even if we played for the next week. I considered going home to my laptop and my MILF sites but I decided to stay where I was.

As I was sat there drinking my pint I felt a tap on my shoulder and looked up and stood there was a woman, "Do you mind if I sit here, all the other seats are taken?" she said.

"Not at all, there is no one sat here, feel free." I said and turned back to my drink. My visitor struck up a conversation with me.

" I have been watching you for a while and you look really sad, is everything okay?" she asked. I told her that I supported the team that were losing so I was not having a good night. "Why are you here all alone, where is your girlfriend?" she quizzed.

"I don't have one, I haven't had one for a long time" I said rather sadly.

" A good looking guy like you and you are single, there is something wrong there." She said cheekily.

" Are you having a laugh or trying to make me feel better, women are not interested in me", I carried on "My last girlfriend was 2 years ago and it was a total disaster, I misread the signals and when we were getting fresh one night I got carried away, copped a feel and received a slap around the face and that was that, I was dumped." "Why am I telling you this, I don't even know you?" I said

"Because it is good to get things off your chest, by the way my name is Sophia, What is yours?" she asked.

"Jack",

"Pleased to meet you Jack, now what were you saying now we have been introduced".

"I wasn't saying anything really as I am really embarrassed about it. Apart from a slap around the face I have never got passed first base with a girl or woman."

"You mean to tell me you are a virgin?" she asked with a strange look on her face, one that I had not seen before.

"Yes, I am" I said looking down at the floor embarrassed and blushing.

"There is nothing wrong with that, it is just that you have never met the right person yet. Don't be in a rush, it is okay, honestly" she said and laid a hand on my hand. "Jack, how old are you, if you don't mind me asking?"

"I am 20 years old, can I ask how old you are, you don't have to tell me if you don't want to, and I know you are not supposed to ask a lady her age." I quickly added.

"How old do you think I am?" Sophia asked. Shit I thought, if I get this wrong I could be in trouble.

"Erm.... I think you are about 35" I said with my fingers crossed. A smile broke on her face "Is it your turn to have laugh and make me feel better. I am 43 next week" she said and laughed.

"I honestly thought that you are about 35, can I say you are very nice. I like the way that when you smile you have little dimples in your cheeks and your eyes seem to shine when the light catches them in the right way."

"Thanks, I don't get many compliments anymore" Sophia said and it was her turn to blush. "Do you want a drink?" I asked.

"Vodka and tonic please" she said. In a minute or so I was back with another pint and a v&t.

"Can I ask you a question Sophia, why are you here alone, you must be spoken for because you are lovely?" It was her turn to look sad,

" I have been single for 4 years since my last partner left me for another woman."

"Is he mad" I said before I realised I had said anything, "sorry for that but I just think he is nuts, I can't understand why he would leave you for someone else"

Again Sophia put her hand on mine and said," you are sweet but I can't compete with a woman 10 years younger than me. She had it all in the right places whereas I am starting to head south if you know what I mean."

"You should never put yourself down; you are a knockout as far as I am concerned." I said, "I would never look elsewhere if you were my partner, why go for a burger when you have steak at home."

"Bless you" was all Sophia said but looked at me in that way again.

I looked at the screen and we were now 4 down so I said," I am sorry but I have to leave now, but could I see you again, if you are not embarrassed to have a 20 year old with you?"

"I would love that; will you walk me to my car in the car park?" Sophia asked.

"My pleasure" and we got up and walked out of the pub into the dark outside. No sooner had we got outside and Sophia took hold of my hand and held it as we walked to the car.

" I have had a really good time tonight, I nearly didn't come out but I am glad that I did because I would never have met you." Sophia said and squeezed my hand. When we got to the car Sophia pulled me to her and said," would you like a kiss"

"Absolutely as long as I don't get a slap in the face afterwards, I laughed"

"It depends what you do doesn't it" Sophia said with a little giggle and with that she offered me her mouth and I tentatively kissed her before getting a bit bolder and breaking into a full blown kiss." You are not a bad kisser, Jack" Sophia said before kissing me again but this time opening her mouth a little. I let my hand slip down her body and put them on her waist before moving down just a bit and laid them on her bottom which was lovely and soft" That is nice, keep going" she said between kisses and grabbed my bottom as well. I pulled her to me again and made sure that she knew I was turned on; I ground my erection against her stomach as she was smaller than me. Again she groaned and kissed me more until I thought that I would pass out from the sensations. Finally we ended the kiss and just looked into each other's eyes drinking in the look of lust on each other's faces.

"Where do you live, can I drop you off." Sophia asked.

"About ½ mile down the road, I would love a lift, I am not sure these jelly legs would get me there."

"Well get in" she said. I opened the door for her and watched her get in. From where I was stood I could see her straight on and as she got in I innocently got a look between her legs but not high enough to see anything really but enough to get my imagination going into overdrive.

About 5 minutes later we were parked outside my house and exchanging numbers before another one of those toe curling kisses and that was it. For tonight anyway, I arranged to ring her the next day to sort out meeting up again.

I quickly spoke to mum who was in the living room before excusing myself and going to bed to relive the events of the night and play with myself before falling asleep.

Chapter 2

I woke at 8am with a smile on my face, had last night really happened? Had I got together with a real life MILF? I couldn't wait to ring her but I thought I had better wait a bit and started to remember last night and before long I had a raging hard on and started to slowly stroke my cock reliving the sensational kissing and the feel of her body against mine. It didn't take more than 30 seconds until I was shooting spurt after spurt of cum on my stomach. I laid there happy with a softening cock still leaking cum on to me but I couldn't care less. Finally 9 o'clock arrived and after a tidy up I rang Sophia, she answered in a couple of rings and my mouth went dry and my heart rate shot up." Hi Sophia, how are you this morning" I almost squeaked before clearing my throat.

"Fine Jack, it's good to hear from you, I wasn't sure if you were going to call. I was thinking to myself why would a good looking guy like you be interested in an older woman like me." She said

"I told you last night that you are beautiful and to be honest I don't feel anything different today, if anything I like you more." I said reassuringly, "So let's not have anymore of that talk. What you up to today?" I asked.

"Nothing, just hanging around the house, would you like to meet up?" She asked with a sexy sound to her voice.

" When and where" I blurted out, I wasn't bothered about sounding desperate I just wanted to see her.

"I'll come over and pick you up in an hour and then we can decide what to do then." Sophia said sexily.

" I can't wait, see you soon" and I blew her a kiss down the phone before hanging up. I rifled through the wardrobe and found my best trousers, shirt and shoes and got ready. I have never been one for aftershave but I put on some that my mum had bought me for Christmas. I checked myself in the mirror and still could not put my finger on what Sophia saw in me. That hour was the longest hour I have spent in my whole life waiting for her to turn up but eventually I saw her car pull up outside and after saying bye to mum I rushed out the door and jumped in the car. I could not believe my eyes when I looked at Sophia, she had her hair up, had on a lovely pink fitted jacket and skirt that showed off her best bits which were her breasts and legs. "Wow, you look amazing" I said almost drooling.

"Why thanks, this is just something I threw on this morning" Sophia said with a twinkle in her eye.

I leaned in for a kiss and her perfume and beauty made me light-headed. After a while kissing we set off.

"Where do you want to go? My treat", said Sophia.

"Let's go for a coffee somewhere" I said, there is one just down the street. Within minutes we were there and I quickly got out the car and went around to Sophia's side to open the door for her and after taking her hand I helped her out of the car but not before seeing all the way to her mid thigh as her skirt had rode up her legs a little way. It wasn't high enough to see if they were tights or stockings but it got my pulse going all the same with thoughts of what was hidden beneath that lovely skirt and I felt a stirring in my trousers. We walked arm in arm into the coffee shop and turned a few heads as we did. We found a booth near the back of the shop and ordered the drinks and cakes.

"I really enjoyed last night, you cheered me up and never in my wildest dreams did I think that I would meet such a beautiful woman when I went to the pub." I said as I took a sip of my coffee.

"Why thank you Jack, I haven't been called beautiful for a very long time" said Sophia and she leaned in and kissed me, I reached up and held her face in my hands and kept the kiss going, it was amazing. "Why do you think I am beautiful Jack, tell me..." Sophia said with a lovely tease in her voice.

" Where do I start? Apart from your dimples when you smile, you have a beautiful face, I love the way your hair comes down around your face, it is like the most amazing painting." "Do you prefer it up or down, my hair that is" Sophia almost purred at me looking me straight in the eyes.

I locked eyes and trying to sound as sexy as I could said," you look hot either way, you are so sexy and you turn me on so much" with that I leaned in for another kiss and this time I pushed my tongue against her lips and she opened her mouth and we French kissed for what seemed like ages. If we were cartoons there would have been steam coming out of my ears, my legs would be ramrod straight and my socks would have been blown off. As it was there was something that was ramrod straight and I shifted in my seat trying to adjust myself without being noticed but I didn't manage it.

"Am I making you hard Jack" again Sophia looked me straight in the eyes and I just nodded. "Come and sit next to me so we can be closer" she said patting the space next to her. I shuffled around and realised that we were completely hidden from peoples view because of the high back of the booth and the fact that the table had a solid middle underneath to stop people from kicking others accidentally when they were sat down.

When I got next to Sophia she took hold of my face and kissed me (I know it sounds like a cliché) like I have never been kissed before, I thought I had died and gone to heaven. She took my bottom lip in between her teeth and lightly bit on them before sucking on my tongue, I honestly thought that I would cum in my pants if this carried on but I managed to get it together. As we were kissing Sophia broke away and said" May I?"

I wasn't sure what she meant so I said "yes" so we could get back to kissing. As we continued the kiss Sophia dropped her hand down into my lap and started to run her hands across my bulge in my trousers and before long she was holding my erection through the material.

"Fairs fair" she said and took my hand and placed it on her leg and to make it easier for me parted her legs a bit. So as Sophia was playing with my cock in my trousers I started to stroke her leg, tentatively at first, just moving a little bit and then moving more and more until I was very near the top of her thigh, I could feel the heat of her panties and was longing to see them but contented myself with just stroking a thigh for the first time in my life.

I broke the kiss and with a voice that was just dripping with lust said" oh my.... I can't believe we just did that in a coffee shop. I would love to do it again."

"Later on darling" she said and lightly squeezed my cock. We finished our coffees and fed each other cake with our forks, Sophia made a big thing about sexily licking the fork clean every time I offered her some cake and it turned me on. Before we knew it we had finished and after another steamy kiss we walked back to the car arm in arm. As I walked in front of the shop I dropped my hand down on to Sophia's ass and gave it a little squeeze as we passed the window.

" Ooh that is nice darling" she said and nipped my earlobe with her teeth.

As soon as we got in the car we fell into each other's arms and kissed again, another one of those toe curling wish it would never end kind of kisses that gets your heart racing and your juices flowing. I let my hands roam and squeezed her ass as we kissed before moving them up her back and brushing the sides of her breasts before going back down to her ass again. Sophia broke the kiss and said in a sexy husky voice," I think we ought to stop before we go too far. Let's find somewhere more private to stop" and with that she trailed her finger nails over my cock through my trousers and I saw it visibly twitch as she touched me.

We drove to a secluded spot overlooking a valley; there were trees on either side of us so the only access was from behind us. "Come here" I whispered as I leaned into Sophia and before I knew it we were kissing again and this time it was Sophia who let her hands wander, within seconds she was holding my cock through my trousers again and stroking it up and down slowly, I could not believe what was happening, here I was with a knockout beautiful, sexy woman and she was playing with my cock. As I laid my hand on Sophia's thigh she opened her legs so I could reach higher. I looked down and saw my belt being pulled open and Sophia slipping her hand down the front of my trousers into my underpants before closing her fingers around my cock and resuming the stroking. I moved higher on her thighs and reached my goal, her panties. I could not believe it but they were wet and I could feel her course pubes through the material, I just held her through her panties and tried to massage her. I seemed to have some success because the next thing I heard was a deep groan and Sophia started to stroke me faster.

"Careful darling, I don't want to come in my pants" I almost panted out.

"Sorry, that would not do now would it" and with that she started to kiss down my body before opening my trousers and pulling down my zip," May I?" and to answer her question I lifted my ass off the seat and she slipped my trousers and underpants down my thighs and for the first time Sophia saw my naked cock. "Oooh that looks nice" was all she said before she stuck out her tongue and licked the end. I am not built like a stallion and my cock is only 6 inches long but she treated it like the most precious thing in the world. I was in heaven, light kiss after light kiss on my cock made my head spin before I saw her open her mouth and slip my cock inside.

I had read many times on line about this but never experienced a blow job before, it was amazing but I could feel myself about to cum within about 30 seconds and with a grunt and a thrust of my cock I exploded in her mouth. 4 spurts later I was finished and Sophia got up, licked her lips and whispered in my ear,

"You taste lovely, it is ages since I tasted any cum."

"You were amazing, that was awesome" was all I could say as I tried to get my breath. I made myself decent and turned to Sophia, "Do you mind me asking, but can I see your panties, you see I have a thing for white cotton full panties, not granny panties but not thongs."

"Your wish is my command" said Sophia, "What do you think I am wearing" she quizzed. "Well I couldn't feel a panty line when I held your ass earlier and I think from when I felt your panties earlier I am sure they are cotton." I said. "You are right" she said as she lifted her ass off the seat and did this weird wiggle dance to get her skirt up her thighs before opening them for me to see properly." Do you like what you see?" Sophia purred. Before me between Sophia's thighs under her skirt were a pair stockings and white cotton panties and I could see a patch at the front that was slightly darker than the rest. I leaned in and took a deep sniff. I have never smelt anything so beautiful in my life. The essence of a woman was right there. I could smell her musky smell which sent my head spinning again and it was my turn to say

"May I?"

"Go ahead darling" Sophia said as she guided my face to her crotch, the closer I got the stronger the smell was and I could clearly see the pattern made by her pubes. I buried my head in her panties and started to kiss and nuzzle them which brought a groan from Sophia. I stuck out my tongue and licked my first crotch and it was the nicest thing I have ever tasted in my life. I got bolder and took the edge of her panties in my fingers and lifted it so I could see underneath and saw for the first time a real pussy, the hair was all matted from her juices and I couldn't help myself I touched my tongue on her pussy lips before slipping my finger inside a little way, Sophia was so hot that my finger slipped in easily and before I knew it my knuckles were resting against her pubes. Another groan escaped her lips and she lifted her hips up to meet my fingers. I started to move my finger around but didn't really know what I was doing but I was enjoying it all the same.