Shortly after the first professional shot pictures of my sissy girlfriend went online the inboxes were filled to the brim. Most of the messages were horny men asking for more a pictures, telling my girlfriend that they wanted to fuck her or just were saying something pointless like hi or hey. My girlfriend clearly liked the attention she got. The compliments made her more self conscious. It all made her hungry for more.
Luckily there were some serious job offers buried beneath all the spam and horny messages. Some people actually really wanted to book my sissy girlfriend for a photo shooting for their businesses and web pages. Due the fact that I had more experience with business things – thirty four year me had seen a fair share of negotiating in his life – I handled the requests.
Most of the requests led nowhere: The first conversations went silent when I told the potential customers that my girlfriend wasn’t available for erotic or pornographic shootings. The next, and the by far biggest part of requests dropped when I told them that some sort of compensation has to be made.
In the end there were five possible clients left. I showed them all to my girlfriend, she had the last word and so she vetoed against two of the five. So I tried to set up shootings with the remaining three. Two were a pain in the backside to work with, setting up something with them just was not doable.
Working with the last remaining client went smooth. He was selling used cars, he was planing to run a local add campaign and he needed something good looking, something that distracted from the junk cars he was selling, on the pictures. He even made a payment in advance to show that he was serious about booking my girlfriend.
But the about forty five year old car salesman insisted on one little detail: He wanted to met the model he was paying for beforehand. When I told my girlfriend about it, she was okay with meeting the future client: “I am all in. Set something up and tell me once you are done doing so.”
I did what she told me to do. I set up a dinner date with our client. He choose some nice Italian restaurant. When I told my girlfriend about it, her reaction was an honest one: “At least the food will be good.”
When we entered the restaurant a couple of days later my girlfriend was dressed to impressed. She caught next to everyone’s eyes when a waiter walked us towards our table. There the client, the car salesman was already waiting for us. To our surprise he wasn’t there alone.
A woman in her mid thirties – the salesman was in his mid forties – was sitting next to him. After introducing each other, the woman was the salesman’s wife and she was also the photographer for the upcoming shooting, we all sat down and ordered the first round of drinks. To my surprise, no one ordered an alcoholic beverage.
We mostly talked about the upcoming shooting, their plans and expectation and adjusted those to what my girlfriend was willing to do. We had a few laughs while doing so, we got along, there was more than just some chemistry between the four of us.
After dessert we finalized a date for the shooting, we finalized the amount of money they were going to pay, then we all shook hands, the clients told us that the will send us some paperwork to sign during the following day and then we all went our ways again.
On the next day, the paperwork arrived in my inbox. My girlfriend and I carefully read it all, we even sent a copy to a lawyer to make sure everything was okay with it. A couple of hours later my lawyer green lit the contract. Then it got signed and sent back. My girlfriend had her first paid gig as a model. We were more than just excited. It was more or less all she was talking about for the following three weeks. And we were celebrating the occasion in our own way: We went out on a romantic sunset picnic.
It was Friday late afternoon when my girlfriend were on our way towards the mountains next to the city we were living in. The mountain range was facing west, the weather was sunny, but some nice white clouds were up on the sky. Perfect conditions for a gorgeous sunset.
After some searching we found a perfect place. Not too far away from the next bigger path – we had to get back home in the dark – but far away from it to give us some much needed privacy.
The first thing we did after arriving was building up camp: A blanket on the floor, putting our food supplies within reach and checking that there were no sharp stones or broken glass in our immediate surrounding. Then we sat down and enjoyed the show.
It was was beautiful sunset. The sky was colorful, the mood was great, my girlfriend and I enjoyed the sandwiches we brought with us while watching the sun go down, while cuddling next to each other.
When it got dark and the lights in town were going on my girlfriend and I shared a few gentle kisses. It was amazing out and up there. And yes, kissing and touching, it raised the horny levels to a point were we just lost it.
The gentle kisses turned into passionate ones. Our hands were all over each others bodies. More and more tension was building up. I wanted her, and she wanted me. Shortly after we began to tear the clothes of each other’s bodies.
While our clothes were flying through the air my girlfriend and I shared one passionate kiss after the other.
Once my hard one was set free he disappeared in her mouth. Her lips wrapped themselves around my dick while she took me deep. Deep down her throat. It felt nothing but good. It didn’t took long and I had to moan out loud.
To make things even better she squeezed my balls. With both of her hands. She brought me close to an orgasm. Then she kept me on the edge for some time. I was about to loose my mind. I was desperate for a relief. I was ready to do anything for an orgasm.
And my girlfriend, she knew about that. She took advantage of it. She pulled my dick out of her throat, out of her mouth. Then she looked at me. She gave me a few gentle kisses and then she asked me to fuck her: “Don’t forget, you lick a hole before you fuck it.”
My mouth was watering the moment she asked me to lick her dirty hole. Then she went in position, down on all her for, ass high up in the air, her ass cheeks spread as far apart as she was able to do. Before I dug in I enjoyed the view she gave me. It was still bright enough to see her tasty looking fuck hole and her caged, but nasty juices spitting clitty.
I liked her tasty looking cute balls for some time. It made her moan out load, it made her clitty spit out even more nasty sticky juice. Then I went upwards, my tongue landed on her fuck hole. The longer I licked her dirty hole, the more intense her moaning got.
My rock hard dick was spitting pre cum while I was eating her out. It came to point were I just had to fuck her. I had to stick my hard dick deep inside her tight fuck hole. So I grabbed the lube, I drowned my dick in it and I poured plenty of it on her asshole.
Then I went in position. Then my glans pressed against her asshole. Then I slid my dick inside her. Slowly, steadily and bareback. We both moaned out loud when I went in. Fuck, it felt so good.
I fucked her gently first. I gave her time to adjust her to the feel of it. She wasn’t pleased with my doing. She told me to go in hard and deep. I complied. I fucked her as hard and as deep as anyhow possible.
It felt better and better with every thrust I gave her. Both of your minds drifted off elsewhere. Her boobs, her caged clitty and her balls were bouncing back and forth with every thrust I gave her. It must have been a joy to watch.
I fucked myself, I fucked her towards an orgasm. I just had a couple of thrusts left inside me. Luckily her hands were already grabbing on the blanket that was laying beneath us. She was close too.
One hard and deep thrust followed the previous one. Then my dick went out off her fuck hole, then back in. Hard and deep. And boom, I came. My balls unloaded themselves. I creamed her. I dumped a huge and nasty load deep inside her.
The moment my balls dumped their load her body began to tremble. Her moaning stopped. She collapsed on the blanket. She was gone. I fucked her elsewhere. A couple of seconds after she had broken down, I collapsed onto her. Fuck, what an awesome fuck.
When we were ourselves again I turned on the flash light laying next to me. First I cleaned her ass and my cum off my dick. Then I checked the immediate surrounding for our clothes. It took me some time to find them all.
To my surprise, I found some fresh cum stains not to far away from the blanked we were fucking on. Some perverts probably had been watching and jerking while my girlfriend and I had fucked ourselves elsewhere.
When I told her about it, a smile appeared on her face: I hope they come closer the next time. I’d love to have their cum all over me. Yes, my sissy girlfriend, she loved dicks and cum.
After we had found most of clothes – my girlfriends panties went missing – we got dressed again, we fixed ourselves as good as we could, then we packed the rest of the stuff we had brought with us and walked towards the car.
On our way home we talked about the evening. We agreed that we both had a blast. After arriving back at home we both took a shower, we brushed our teeth then we went to bed. She was dreaming of her first shooting and becoming a super model, I was dreaming of her, my damn hot sissy girlfriend.
Source: reddit.com/r/eroticliterature/comments/13343ww/a_sissy_takes_off_m34f25_rimjob_anal_deepthroat