This is a true story. If it weren't true it might be more interesting but I wanted to write something that has it's value in being completely true...
I'm only changing names.
***
My boyfriend was out with his friends at the bar, since I wasn't 21 I couldn't join them. I was sitting at home completely alone and drinking wine. I was on the internet looking at porn starting to be get pretty tipsy and pretty horny. I have no idea why, but I posted a CL ad offering to fuck for money. The emails started pouring in....so much more than I expected. I live in a relatively small midwestern city....a college town though.
I weeded through the emails, drinking more as I did, and selected what I thought seemed like the most legitimate candidate. He left a telephone number to text in the email and I replied telling him it would be $100. I had no idea how much to charge...but I remembered that Julia Roberts charged $100 in Pretty Woman, so I did the same. My make-up was already done, I was dressed in denim shorts and a dark purple v-neck, my black hair was shining and bobbed, and my pussy had been freshly shaved earlier in the day.
I started to drink more and faster in an attempt to drown out my nervousness. I couldn't believe I was actually doing this...but I was curious for the experience...the thrill of fucking some stranger for money. I definitely couldn't have gone through with it if I weren't drunk.
The man was referring to me as 'baby' through the texts, and I gave him the address of a nearby street corner...I was paranoid of anyone seeing me get in the car with some man. I paced around for awhile, gulping wine until I knew I should start walking down to the corner. It was around midnight at this point and I left the house and started walking down the street. It was dark but in mid summer and very warm.
I got to the appointed corner and stood around for a minute or two until a car pulled up and asked me if I was Rena, the fake name I had decided to go by. I walked up to the car, opened the door and got in.
I surprised myself with how talkative I was being...I tried to remember things about hookers I had read in pulp fiction novels and stuff..that I should be friendly and comfortable seeming....eager to please. He was a Romanian foreign exchange student at the law school, he told me at least, and that he was 28. I told him it was my first time doing this kind of thing...It's funny because I doubt he believed me. He said his friend was letting him use his apartments for our meeting and drove to a part of town I wasn't really familiar with.
We finally got to an apartment complex and walked to the second story where he opened the apartment door. He led me to what seemed like used to be a child's room. There was a queen sized bed, no other furniture or any little trinkets, but children's ABC wallpaper. It was kind of creepy.
I asked for the $40 upfront like we had agreed upon and he handed it to me and I placed it in my pocket. I kind of awkwardly stood around until he gestured that he would like to move on.
I went to turn out the light...my shyness poking through the veil of alcohol...but he quickly and sternly said, "No, I like them on." Of course.
I left it on and took off my shirt, revealing a cheetah print bra with my C cup breasts squished inside, then I undid my shorts and slid them off. I had never gotten completely naked in the open and light for my first time with anyone before...Actually, I had only had sex with 4 men at this point. Finally I undid my bra and slid down my black lace panties, looked over at him and then laid on the bed.
He quickly got undressed and asked me to suck his cock. It was an averaged sized dick... not surprising for his frame. The guy was probably around 5'8 and weighed probably 170. He was still much bigger than me, 5'3, petite with soft curves.
I sucked his cock as he lay on the bed for what seemed like a super long time. And finally he rose and pushed me down on my back, spread my legs, and started licking my pussy. He licked my pussy for a few moments...not doing a particularly good job....before putting a condom on and climbing on top of me and entering me. I was surprised that my pussy had been so wet that it let him slide in with ease. I blushed and felt embarrassed and slutty that I had been turned on without even knowing it.
He was fucking me in missionary position very quickly and sloppily kissing my whole face. He told me to raise my legs up and spread them as wide as I could, which I did. I remember looking up at the ABC wallpaper and just still not believing that this was really happening. It felt so surreal.
After a couple minutes he groaned and rolled off me...he had came. But almost immediately he removed the condom, was squeezing my tits, and then placed another condom on and was already for round 2.
He grabbed my hips and pulled me up to my knees and pushed me into position on all fours. He asked, "You do anal, right?"
I was kind of shocked because I never had and didn't expect that someone would even request it. I said that I was sorry but I didn't and he just kind of grunted and stuck his dick in my pussy, but from behind. He fucked me like that for awhile before stopping and laying on his back on the bed. He beckoned for him to get on top and I tentatively did.
"Come on and ride me." He said. I started slowly bouncing up and down on his dick while he told me to go faster and faster. "Ride my cock. Faster. Faster." He demanded my squeezing hard on my ass. I was riding his dick so hard and fast that I finally felt close to cumming. I started moaning and yet was wondering if he thought I was really moaning from pleasure or faking it or if he even cared. I was actually coming super close to cumming and couldn't believe it was actually feeling good. I had never cummed before having sex with a guy for the first time....it usually took getting used to each other and growing to feel comfortable. But here I was wildly bucking on this stranger's cock....something I never did on first times either since I always stuck with missionary...my tits bouncing everywhere....and moaning like a whore. I was being a whore though, I guess, huh?
And finally I came....a warm wave and sublime explosion...I squealed and could feel my cunt contract on his dick. I kept riding him but more slowly and seconds after he came too.
I got off of him and he removed the dripping condom and threw it in the wastebasket. I remained laying on the bed....not knowing what to really do. He laid down beside me and began making small talk. I asked him if he had ever paid for sex before and he said yes, many times and that in his country it wasn't a big deal. He told me it was actually harder to have sex with girls in America and he had only had sex with one girl here.
After a few more moments of small talk I noticed his dick was once again hard and he asked me to fuck him again. I at this point was feeling really sore and told him so, hoping to get my money and go home. But he asked me to suck his cock instead then and I was too nervous and submissive to refuse.
I took his dick in my mouth and began sucking and bobbing my head up and down it. He put his hand on the back of my head and was forcing me to take all of his dick in my mouth. My gag reflexes started to go off but I tried my best to contain it. My eyes started watering but finally I could tell he was about to cum and I sat up. I'm sure he wanted to finish in my mouth but inside he jizzed into the waste basket.
I got up and started to get dressed and he did the same. He then gave me the other $60 and drove me home....we made small talk about music that was playing on the radio and he dropped me off at the same corner he picked my up on. We said goodbye and I walked home just as my boyfriend and his friends were getting there.
I immediately made up a story of how I walked to a gas station to get a pop and had found $100 in the parking lot. I think I acted wonderfully! We hung out a bit more, drank some more, and then went to breakfast. I paid for my boyfriend and I's meals with the newly earned money. And then we went home and he had sex with me.
While he was on top of me I kept thinking about how I had just fucked that stranger for money and hadn't even taken a shower. I was worried that my boyfriend might somehow notice but he didn't and that was that.
I think back on it and can't even believe that I did it...just completely out of the blue. It seems so crazy and dangerous and I have no idea where I found the courage. I've never told a single other person...not a soul....how could I? It was the one fantasy that I actually went out and made happen...
