Back when I was about twenty years old I was more or less living in a bar around the corner. I hung out there nearly everyday. I had a couple of beers with some friends, we played darts, we played pool or we watched sports together. And from time to time, I successfully hit on women that were hanging out in my bar too. But the only thing that came out of it was a never ending series of one night stands.
Every time some new female face showed up in the bar all single men, some of the taken ones too, jumped onto her. Everyone tried to impress her, to get her into their beds. To fuck them and maybe to fall in love afterwards.
One Friday evening an about forty four year old woman entered the bar. Everyone inside was preparing to make their move. But as soon as they saw that she was good friends with the man behind the bar, the owner of the bar himself was serving drinks that evening, they all pulled back. Better not messing around with the guy that serves you drinks and owns your living room.
Everyone blew off their attack. Everyone except me. Because the woman had caught my eye the second she had entered the bar. I was barely able to keep my eyes off her. I was undressing her with my horny eyes all the time. I wasn’t able to focus, to concentrate on everything else except her. I had developed a more than just serious crush on her. Within the blink of an eye.
It didn’t took long and my state of mind, my behavior came to her attention. She caught me staring at her. She caught me checking out her ass. She had already sent a set of encouraging smiles towards me. But the coward I was, I needed a couple of drinks first before I was able to walk over to her, to initiate a conversation.
After I was drunk and brave enough I walked over to the bar. Then I pulled a classic: “Is this chair next to you already taken?”
The forty four year old woman shook her head: “Not yet, but I fear it soon will be.”
Not getting the hint I looked around, hen I asked her a next question: “Are you waiting for someone?”
A smile appeared on her face. She even was laughing out loud a little bit: “Yes, I am waiting for you.”
Boom, it hit me hard. I felt embarrassed. How could someone be that stupid. Then I sat down, she ordered something to drink for the two of us and then a conversation came up. An interesting one, one that showed that the two people that were talking had some common interests and seemed to get along with each other.
While sitting next to each other, talking, getting a little bit touchy more and more sexual tension built up. It came to a point were the two of us were practically undressing each other with our eyes. We wanted nothing but to tear the other’s clothes of their bodies. We wanted to fuck each others brains out.
To my surprise it was her who made the move. She invited me over to her place. I gladly accepted the invite, I didn’t even had to think a second about it, and then I called a cab towards destination unknown, but in town, as she had told me earlier.
After paying the tab the two of us left the bar. While leaving the bar I noticed for the first time that she was actually taller than me. Not that it was a problem, it just was a first time. I never ever before had been with a taller woman. On my way out of the bar the remaining guys inside, even the owner himself gave me a thumbs up: “Go and get her.”
Over at her place it didn’t took long and our clothes were flying through the air. We wanted each other. We took each other. We didn’t even made it onto her sofa or into her bed. We had our first time on the carpet in her hallway: She on top, I down below on the floor. Our first time gave us an awesome orgasm and a few bloody scratches on my back.
After we came together, we spent the night together. We cuddled, we spooned before falling asleep: She was the big spoon, I was the small spoon. We enjoyed being that close to each other for some time. She gave me a few gentle kisses on my neck before we both drifted off into dreamland.
On the following morning, it was a Saturday, we both didn’t needed to go to work she climbed on top of me as soon as she realized the perfect piece of morning wood between my legs. Again, it came good.
Then we dragged our sweat covered hung over bodies into the shower before we had some breakfast together. During breakfast we decided to spent the rest of the day together. Just hanging out, chilling in front of the TV and fuck as much as anyhow possible.
We kept on going that way until Monday morning. I had to go to work, so had she. But we staid in contact throughout the day. Because that weekend was enough to make us fall for each other. And from that Friday in the bar on, there wasn’t a single day when we weren’t in contact with each other.
In the upcoming weeks we had more than just one date. We went out and had a blast. We went to the movies, we had dinner together, we went into a theater, we ended up dancing at a concert, it was a nothing but awesome time back then. We were falling hard for each other. We became a loving couple. And we didn’t gave a damn on the fact that she was twenty four years older than me.
Time flew by back then. My girlfriend and I were more than just happy with each other. About six months after meeting each other I moved in with her. And to our surprise, living together worked out great. We got along. I was the one that took care of the place, that did most of the cooking while she was the one bringing home the groceries and doing the minor repairs.
But one thing unfortunately had already worn off after six months. Our sex life wasn’t the best anymore. We still were fucking, but the fire was already out. It happened by far too fast for the two of us. We both hated it, but we both were also unable to really talk about it back then. My girlfriend and I, we both were hoping for a miracle to fix the situation.
And that miracle actually happened. One day, out of curiosity I came up with the great idea to put on one of my girlfriend’s panties after I got out of the shower. I thought that I was home alone, that my girlfriend was out getting some groceries, so I took my time while wearing them. I posed with them in front of the huge mirror we had in our bedroom. I even took a few selfies while doing so.
And I must admit, I loved it how the panties looked on my hairy male body. I also loved how they felt on my skin. And yes, wearing panties – back then it wasn’t sure if it was wearing panties or the fact that my wife had worn them before me – was a huge turn on for me.
It didn’t took long until I began to take care of the next to perfect piece of hard wood between my legs. I took my time with jerking off. I just pulled the panties to the side to set my boner and my balls free. I watched myself in the mirror doing so. And damn it, watching myself with a hard one while wearing panties, it rose my horny level to previously unknown height.
I gave myself one gentle, soft stroke after the other while my other hand was squeezing my balls a little bit. I kept on going for some time, I was in no hurry, I enjoyed the sensation of it while my mind drifted off elsewhere. While my brain slowly but steadily turned off. While I lost track of my surrounding, time and everything else.
All that mattered was one of my hand going up and down my rock hard dick while the other one was squeezing my balls. My moaning was filling the bedroom as I worked myself towards an orgasm. One thrust after the other. It felt better with every stroke I gave myself. It all felt nothing but good.
I was gone. I was elsewhere. So I didn’t realize that someone else was in the room with me. It was my girlfriend. She had came home from grocery shopping. She was watching me playing with myself. She had already scattered her cloths on the floor and was playing with herself. Because watching me wearing panties while pleasing myself in front of a mirror was nothing but a turn on for her.
It didn’t took long and just playing with herself wasn’t enough for her anymore. She wanted more. She wanted my rock hard dick filling up the wet and needy hole between her legs. So she came over to me. She placed her steps careful to not disturb me. Then she placed herself behind me and gave me one gentle kiss on my neck.
I froze. I had a minor anxiety attack. I got caught. My girlfriend caught me jerking off while wearing her panties. I was more than just afraid that she would be mad. But she wasn’t. The moment she realized what was going on with me, she whispered the following into my ear: “That was by far the hottest thing I have seen since I can remember. Let me jerk off your dick for you.”
Moments later one of her hands was going up and down my rock hard dick. She jerked me off the same way like I jerked myself off before she had interrupted me. It didn’t took long and my brain was melting away again. Her hand going up and down my rock hard dick, her hand squeezing my balls was a much bigger turn on than doing it myself.
She brought me closer and closer to an orgasm for some time. She gave my pre cum leaking cock one stroke after the other. I was ready to cum. My aching balls were ready to unload themselves. She knew that I was close to an orgasm when she whispered something into my ear again: “Not now, later. Later will be better.”
Then she took her hands of my dick and off my balls. She stopped jerking me off. Desperation set in. I wanted to cum. I even was begging her to cum. But my girlfriend had other plans. She turned me around, she looked me in the eyes and then we shared a few passionate kisses. Those kisses drove the frustration out of my body.
After some time kissing she made me lay down onto the bed. She made me lay down on my back with my still rock hard dick pointing towards the ceiling. Then she climbed on top of me. She placed her dripping wet pussy above my face. At first she let me smell her scent, then she slowly lowered herself down until my tongue was inside her cunt.
I enjoyed every second of it. Eating her out, tasting her delicious pussy juices while being trapped between her legs, it was nothing but a turn on for me. It all made my rock hard dick gushing out pre cum.
It didn’t took long and my girlfriend’s moaning was filling our bedroom. She began to loose herself while my tongue was inside her dripping wet pussy and on her tasty clit. She had an orgasm while she was sitting on my face. She came all over my face. And now she was warmed up. Warmed up and ready for more.
Moments later my rock hard dick was sliding in and out of her pussy. She was on top, she rode me cowgirl while my hands were on her boobs or on her ass. It didn’t took long and we got lost. Our brains were turned off. All that mattered was my rock hard dick going in and out of her dripping wet pussy.
Now our moaning was filling the room. She gave me, she gave herself one hard and deep thrust after the other. She fucked us closer and closer towards an orgasm. We kept on going for some time. In and out. One thrust after the other. Until her hands began to clench my tights. Until my hands began to squeeze her ass cheeks.
We both were close. Just a couple of more thrust. And then one more. And one more. And then boom, the tension left the room. We came. Our bodies were shaking. Inside our heads two fireworks went off when my balls unloaded themselves inside her pussy.
Shortly after we came together my girlfriend collapsed onto me. We both were regaining our breaths. It took us some to be ourselves again. It took some until we were able to look each other in the eyes while probably thinking out the same: “What had just happened to the two of us?”
We both were happy with what had happened, but we wanted to figure out why. Because we might have accidentally discovered a way to bring the sparks back into our sex life. To revitalize our sex life and to a certain degree maybe even saving our relationship.
So we dried it again, on the next day. I once more wore some of her panties, and it worked. I was turned on, she was turned on, the sex was awesome again. And to be totally honest, wearing her panties, it had awoken something else inside me. Something that I though that wasn’t even there: My feminine side. It didn’t took long and I wanted more than just wearing panties before and during sex.
Source: reddit.com/r/eroticliterature/comments/114tpxc/how_she_turned_me_into_a_woman_m20f44_romance