Diary 16: Renting a Sex Worker
Chapter 76
It was another beautiful day in California. It was my 25th birthday, and I had just finished celebrating by going out with my friends to a nice dinner. After a couple of drinks, we were having a good time, laughing, and joking around. We had gone through a lot together and had a close bond. My friends had always joked about me being a virgin and not ever getting any pussy. They always tried to set me up with girls, but I just never found the right one.
My friends were sitting there laughing and joking, and they started talking about sex, like they always did. They were sharing all of their crazy sex stories and experiences. I just sat there sipping my drink, looking at them in amazement and wishing that I had even one story to share.
“Dude, you got to get some pussy,” one of my friends said. I looked at him, and he continued, “We should just hire a prostitute for you.” They all laughed and agreed. “It’s your birthday, so we will call this a birthday present.”
I sat there speechless. It would be a crazy idea, but in a way, it was very tempting to lose my virginity to someone who knew what she was doing and wouldn’t judge me if I did anything wrong. I thought it over for a minute and decided that it would be a once-in-a-lifetime experience and that it might help me out when I’m with girls in the future.
“Alright,” I said. They all cheered and gave me high fives. We decided to head back to my friend’s house for the night, which had a hot tub, and they told me that they would order the girl in the morning. I was excited but nervous at the same time. I couldn’t believe that I was going to have sex with an escort. We all went to bed that night, and I had a hard time sleeping from excitement and anticipation.
The next morning, my friends ordered her, and we decided to relax at the pool while we waited. I kept asking them what it would be like and what we were going to do, but they kept telling me that it was a surprise. We were relaxing, listening to music, and drinking beer while we waited.
About an hour later, they called us to tell us that she was here. We all rushed into the house and were waiting at the front door when they walked in. She was wearing a black thong bikini and stilettos. She was a beautiful blonde with nice big tits and a skinny waist. I was speechless when I saw her.
My friends introduced her, and I said hi. My friends asked her if she was ready to get started, and she said that she was. They told her that I was a virgin, and that they wanted to show me the ropes, and teach me how to give a girl an orgasm.
My friends told us that we were all going to the bedroom. They had bought some sex toys, handcuffs, and whips. They told me to take off her clothes and to get the toys ready while they were undressing.
I went over to the girl and took off her top, then her bikini bottoms. She was completely naked, and I was admiring her body. She was so sexy. I took off my clothes and got on the bed with her.
My friends came into the room naked and had their cocks in their hands. I had never seen them naked before. One of my friends was bigger than the other, but both were bigger than me. They walked up to the bed and told the girl that they were going to warm her up for me. She smiled and said that she was ready for them.
I just sat there in amazement watching them. The bigger of the two guys got up on the bed first and laid down next to her. He started kissing her all over her body and sucking on her tits. He slid down her body until he was between her legs. He spread her lips apart and licked her clit. He was going crazy down there, licking her clit back and forth and shoving his tongue deep inside her pussy.
She was moaning, and her body was shaking. He kept licking her until she had an orgasm. Her legs were shaking, and she was breathing hard. I was amazed at how good she looked when she was having an orgasm, and it made me want it even more.
My other friend then got up on the bed behind her. He grabbed her hair, pulled her head back, and shoved his cock down her throat. She gagged and tried to pull away, but he held her head in place. She took his cock all the way down her throat and started sucking it. She kept sucking it until he took it out of her mouth, pulled back, and shoved it deep inside her pussy from behind.
She let out a moan of pleasure as he fucked her from behind. My friend was fucking her hard, and I could hear his cock going in and out of her pussy. I watched as it went in and out, making her pussy stretch.
They both continued to fuck her for a while until she had another orgasm. This time she squirted all over the bed, and my friend pulled out and cummed all over her ass.
My friend who hadn’t had sex with her yet laid down on the bed and told her to suck his cock. She got up and straddled his chest. He grabbed the back of her head and shoved his cock deep into her throat. Her lips were stretched around his cock, and he held it there. She looked up at him with her eyes watering and her mouth open wide.
He pulled it out of her throat, and she took a deep breath. He grabbed her head again and shoved it back into her throat. He repeated this for a while, making her throat fuck his cock.
After a while, he pulled his cock out of her mouth and told her to get on all fours. She did what he said and got into position. He then got up behind her and shoved his cock deep inside her pussy. He fucked her like a wild animal, pounding away at her pussy while she was screaming in pleasure.
I watched as his cock went in and out of her, making her ass shake. I wanted to join in so bad and wanted my friends to teach me what to do. After a while, he told me to get up and join in.
My friend pulled his cock out of the girl’s pussy, and I got up between her legs. I put my cock into her pussy and started fucking her. She was so tight, and it felt amazing. She felt better than I ever imagined. I fucked her hard like I had learned from watching my friend. I could feel my cock rubbing against her G-spot, and she let out a loud scream. She was having an orgasm.
I kept fucking her until she had finished cumming, and then I pulled my cock out. My friends were getting ready to do double penetration, which means they were both going to fuck the girl at the same time, one in the pussy and one in the ass.
They had me put on a condom, and I got behind her with my cock in my hand. My other friend got on his back, and she straddled him. She lowered herself down onto his cock and started sucking my cock. I had never been sucked by a girl before, and it felt great. She was sucking it like her life depended on it. It felt so good, and I wanted to cum, but I didn’t want it to end. She sucked my cock until she got on top of my friend and put my cock deep inside her ass. She started fucking both of our cocks until she had an orgasm again. This time we both cummed. My friends pulled out, and we all relaxed for a few minutes.
After we had relaxed a little, my friend told me that he wanted to try something else. He wanted to teach me how to fuck a girl’s ass. He went over to the bag and got out a big butt plug and some lube. He put some lube on the butt plug and put it into her ass.
She moaned and told him that it felt good. He put the butt plug in her ass and moved it in and out. He took it out and handed it to me. I did the same thing as he did, but he told me not to go too deep. I moved the butt plug slowly in and out until he told me that I could put my cock in her ass.
I put some lube on my cock and put it in her ass. It was so tight and felt amazing. I started fucking her slowly, and she moaned in pleasure. She said that it felt good and for me to fuck her harder. I fucked her harder until I couldn’t hold it any longer, and I cummed inside her ass. I pulled out, and my friends cheered. They said that they were proud of me for finally losing my virginity and that I would be good at sex.
They tied her up and blindfolded her while I was still recovering from cumming. They then put my cock in her mouth, and she started sucking it again. I was in heaven and couldn’t believe what was happening. I had always imagined it, but never thought that it would actually happen.
My friends then started fucking her again while I held her legs up. They took turns fucking her pussy, and she sucked my cock. We were in a circle of sex, with each one of us getting a turn. My friends fucked her pussy until she was squirting all over them, and I fucked her ass until I couldn’t cum anymore. We then untied her, and all of us laid down to take a nap.
After our nap, they called a cab for her and thanked her for the good time. They paid her, and she left. We were all sitting there talking about how it had gone, and they were happy that I finally got some pussy. They said that I did well for a virgin, and now that I have been shown the ropes, I can teach other virgins like me.
It was my birthday present, but it also taught me so much about sex and how to pleasure a girl. It will be a memory that I will cherish for the rest of my life. I learned so much and was introduced to sex in the best way possible. I will always be thankful to my friends for giving me such an amazing experience on my birthday. It was the best birthday present that I could have asked for.
The End.