First Time Hooking Up On Craigslist free porn video

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I was 24 at the time. 5’8 tall 190lbs and very hairy. My dick is just under 7 inches and a nice size cut and usually trimmed hair. Not much of an ass honestly and not girly in any way. But I Loved getting fucked like a whore.

I have mostly been attracted to women in my life but have had the occasional experimentation with boys growing up which I may post here later if I feel like it. Here is my story.

My mom called me on the phone during the week one day and asked if I would be able to come over from time to time and watch the house and take care of the dog over the coming weekend. They didn’t live very far, and it really was not a problem so was no big deal.

That Saturday I has really horny when I went over, and the thought hit me to maybe have some fun with myself. I decided that I was going to grab one of my mom’s dildos and give myself a good fucking sense I didn’t have the time to do so normally. After cleaning one that I liked I grabbed a condom and went to town on myself… By the time I had the full length of the toy in my ass craigslist had come to mine and how I wanted to have the real thing.

I laid there with the toy still in and posted an ad “first time looking” after a bit I had a pic and a response that read something resembling “you should let me put my black cock in that tight ass”

After a few messages he was on his way over, and in our text, he wanted me already naked and ready when I answered the door. So, I being a little submissive did as I was told and waited for him.

He was a heavyset black guy with glasses short hair and gym shorts on, looked to be maybe mid thirty.

He seemed nice and gentle enough knowing that It was my first time, so we walked to the bed room and asked if I wanted to suck him off to get started. He told me to get down on my knees for him and I did then after that I didn’t have to take any direction. His pants were off in a second and my face was greeted with his semi flaccid cock.

I want right to work and wasted no time putting it in my mouth to get him hard. It wasn’t my first cock and it wasn’t the biggest, but I remember a musk smell and no taste really at first, but it sure grew to size quickly. I couldn’t deep throat it, but I gave it my best.

He asked if I wanted him to lay down, so I could change the angle. I agreed and got next to him on the bed and started to kiss his balls with some sucking. I did this all the way to his head and slowly wrapped my lips around his cock as I slid down almost the entirety of his cock. I heard a moan escape his mouth, so I knew I did something right. I settled into a little rhythm where I would lick his shaft from top to bottom and then bob my head up and down his cock making it about half way into my mouth for about a minute and repeat.

About 5 minutes into this I felt a wet finger start to play with my ass and boy did it feel good from lightly ringing my ass to fingering me.

7 mins in pulled I off his cock with his middle finger in my ass and asked if he wanted to fuck me now. All he told me was to bend over the bed.

Bent over and completely at his mercy he took his shirt off and put on a condom which we agreed to before. I felt like such a little bitch laying over like that when he applied the lube and I was loving it.

He asks me if I was ready and I said “yes” as I felt both hands spread my cheeks with his cock pushing on my virgin hole.

Thankfully because of my play time before and his slow entrance pain was minimal. He slid it in inch by inch each push checking on me until he had the full length in me and God did it feel good. He gave me some time to adjust and slowly started to fuck me. And there I was laying there bent over a bed completely exposed and at the mercy of a complete stranger fucking me.

He would do a few quick shallow pumps and then slide the length of his cock in me and slowly out. I even got a spanking out of it, I was his bitch for the time being and I couldn’t help but grip the bed and tell him to fuck me harder or even the few times I called him daddy.

It must have gone on for about twenty minutes with a few spots to add lube and readjust onto the bed when I told him he didn’t have to make it last and wanted him to cum for me.

After I said that he laid into me and started really fucking me hard making the bed shake with every thrust. When I could hear him getting close I told him “yes daddy fuck me, … cum in me, please” I don’t know what came over me as he pulled out smacked my ass and slid right back in before I could think.

In less than a minute I felt him tense up and cum.

When I felt him slowly pull out I realized what had just happened… He pulled off the condom and shot a very sizable load into my very willing ass.

The end of the story was uneventful with me cleaning up and him leaving almost immediately as I walked to the bathroom to shower with my now messy ass.

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There was about three months since I last saw her before I heard from her again, one day when I was checking the mail I found a letter with her as a return address, I immediately went inside and opened it and it was a letter from her telling me she had stopped in a couple times but I wasn't home, I was working afternoon shift at a job I'd been laid off of about a month or two before we blast hooked up, she told me she was interesting in having a good time again with me for a few days and gave...

2 years ago
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Meet Hooking Up with My Sex Slut Amulya Pa

Readers of the earlier part might be aware of how I meet with Amulya & fucked her in the Museum. Here is the continuation in Part 2.Part 2 of my Meet & Hook-up with Sexy Slut Amulya - https://xhamster.com/users/sexyamu212. As it was early evening as we left the museum, I asked Amulya to get into my car where I made her sit with her legs up on the dashboard giving anyone interested a nice look under her skirt as I made her play with herself for me while I give her pussy the odd pinch. I...

3 years ago
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Meet Hooking Up with My Sex Slut Amulya

Hello everyone this is a fictional date, sex escapade of how I imagine I would get dirty with my slut Amulya more about whom can be read in the link - https://xhamster.com/users/sexyamu212. Amulya as is well evident is a slut who is always fucking horny & loves to serve her lovers, masters but she was definitely not ready for the events of her first Meet & Hook Up. This part one of a growing series.Without much time wasting I will now start the story of me & Amulya Day 1 - Part1: As...

2 years ago
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Hooking up with an old crush who is currently preg

I had just arrived home from college on spring break the previous day and I was already bored; so bored that I was at the mall looking for any kind of action. I hadn't been able to track down any friends who had spring break the same week as I did and had actually spent Friday night at home with my parents. I had no intention of spending Saturday night the same way even if it meant trolling the mall that afternoon, looking for anyone I knew. Fortunately, things turned out even better than I...

3 years ago
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Hooking Up With A Lonely And Hot Bengali Girl

Hello ISS readers, this is Tushar from Mumbai. I am a 23 years old student studying in the BA faculty and a part-time MASSAGER for earning some bucks due to financial instability. I have a bit long dick than a normal size enough to satisfy any girl or women and fill her with pleasure. I have been following ISS for the last 7 years and this is the first time I am writing about my experience of sex with an elder girl who was my bestie’s girlfriend’s friend. This story started 5 years back in 2013...

1 year ago
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Hooking the bra

Hi every body, its sam again for the iss. But the story is very good, hope u all like it. This happened few years back when i was in college. My aunty is very pretty with creamy white complexion, great pair of boobs, soft and round ass with ultimate sex appeal. She was around 35 years of age and i was 21 at that time. In the middle of june, during the summer vacations, my mother went to my maternal uncle’s house with my sis for one week. I and my father were alone in the house, i heard the...

Incest
2 years ago
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FaceTime surprise

I have a new job working away and I bought an iPad to keep in touch with the wife, it’s great seeing her when away I miss her so much so it’s great when I’m bored in my room. Jane and I for years have spoke about sharing? But she never comes through, it must be 4 years now we have had the same conversation about it and it’s always the same answer maybe! Jane is great in the sack she knows how to please, I keep telling her she needs to give it out cos it’s going to waste on me as I only last...

3 years ago
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Showtime for Teri

Showtime for Teri By Teri Franken Chapter 1 My name is Teri and I am 28 years old. I have been a closet sissy for as long as I can remember. My parents knew that I was not your typical child and they let me live how I wanted to and did not judge me, they just loved me unconditionally. I grew up loving everything that a little boy typically doesn't like, such as dresses and dolls. My parents were concerned that I would be a target for bullies, so I was home schooled, took my GED...

2 years ago
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Eagle in the Sunset 2019Chapter 29 Summertime for Us All

October 17th, 1995, 7:30 AM PT, Metro Plaza Hotel, Los Angeles, CA Miriam had been tossing and turning all night; she spent time just sitting in the chair in the corner of the room to try and let Baruch sleep. She was so upset she was oblivious to the fact that Baruch couldn’t sleep either, which was not in her nature. She was usually fully aware of what was going on with her husband. They thought together almost telepathically, and yesterday had been one of the first times in decades when...

3 years ago
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Timeless Beauty

TIMELESS BEAUTY BY PAUL G. JUTRAS Sam walked in the dorm house, looked at the lock and then in the dorm mistress's room. The plus size woman was dress in a black blouse and flats, black with white palm tree design jacket and skirt with dark brown nylons. She new there was only a half hour before she made her rounds and called lights out. Upstairs, roommates Chris and Alex waited on their beds. Like their friend Sam, both guys were petite and lovely looking. Being transsexuals who...

1 year ago
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Younger Than Springtime

The door was open. I had no reason to have it closed. We were all in this together. So I was sitting in the large chair as my nurse prepared to access my port to begin the first liter of Cisplatin. The cancer center had been busy today and I glanced out the doorway as several people passed by. Then I noticed a woman pausing as one of the nurses escorted her somewhere.It was Katherine. I recognized her at once even though it had been so many years ago. Then I heard her laugh as her companion...

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