Confessions tagged with 'first'.

#4251

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So for a while now I've been hoping to get the opportunity to have some young teen pussy. A gift was sent my way last week. Just scrolling reddit and I see a delicious looking little pussy posted. Click on the profile and the description says she is located in the same state. I figured no chance we are local but send her a message. We started chatting and she loves my pics. Then drops a bomb on me. She says look, I'm only 14 and I understand if that's not your thing just please don't report me. I ended up kind of side stepping acknowledging what she just said and thought maybe it was a fake account. Then we realize that we live less than an hour apart so she asks me to move our chat to telegram. Super nervous it's a setup I do it. Fortune favors the bold I guess. She ends up completely verifying she is actually who she says she is. Nerdy 14 year old girl. Super sheltered and is dying to know what a cock feels like. Has a big daddy kink and wants her first dick to be a grown man. She developed this whole plan. Her dad normally drops her off at the mall on the weekends and picks her up when she calls him. She wants me to meet her there. Skeptical I am interested though. Then she wants to video chat. I agree, last night I'm laying in bed and video chatting with this adorable little 14 year old and she is wrapped around my finger. Sliding her hair brush in her pussy for me. Talking about stupid shit that happened at school that day. 1 point she lays her phone down and I still have audio. Her dad came in and I heard him talking to her and telling her good night and sleep good. Fingers crossed this all goes well. I definitely want to be the first guys who slides his cock down this little girls throat and first 1 to taste her little pussy. After seeing her stuff that hair brush in her pussy I'm guessing she asks me to squeeze my cock inside her if we get into a situation I have her pussy exposed. Wish me luck everyone.

#4159

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Growing up, we lived across from two women. This was when lesbians weren't too highly thought of in our town. Both Tiffany and Deb were in their mid to late thirties. They had a nice two bedroom house with a built-in pool in back. They said we could come over and go swimming anytime we wanted. My brother was three years older than me, and when he was 18 he joined the Army right out of high school. Shortly after school was out I put my trunks on and decided to go swimming. It was hot out and the water felt great. After a bit I got out and was heading home when Tiffany called me over to the back door. I didn't even know she was home. She was in her bra and panties. They both walked around in their underwear quite often, and I often saw them sunning in the back yard when I went over to swim. I walked over to where Tiffany was and she said, "I've been watching you for a while. I recently had a hysterectomy, so if you ever want to practice fucking, just let me know." I was shocked, and pretty sure I turned several shades of red as I hurried home to jerk off.

Both ladies were a little heavy but had big tits. For the next few weeks I jerked off every day thinking about what she said, and made sure I went swimming when they weren't there. Then as June turned into July I was over there nearly every day. One day I must have stayed in the pool a little too long, and before I could get out both ladies came out the back sliding door. They looked at me and unhooked their bras at the same time. As they approached the pool, each stopped and took their panties off. I couldn't help but stare and my cock started rising. How embarrassing for me. I did notice, though that each had a triangle of hair neatly trimmed above their pussies.

They both walked down the stairs into the pool, but didn't approach me. They were in about four feet of water when I saw them start kissing. I had never seen two girls/women kissing before, but it excited me. I was staring at them when they broke the kiss and Deb winked at me. I was more embarrassed. I was a 15 year old horny teenager watching two lesbians making out naked in the pool I was swimming in. I wanted to get out, but couldn't have them see the boner in my trunks.

Tiffany then waded over to me and stood in front of me. She looked down at my bulge and said, "Yes, honey, I like pussy, but I like cock too." As she said that she reached down and grabbed my cock through my shorts. "Shh," she said, "It's okay. I had my first fuck when I was 13, so it's okay." She squatted down and pulled my trunks down and stood back up. She took my face in her hands and kissed me. I felt her tongue part my lips and my cock sprung straight forward. While we were still kissing she reached down and squeezed the base of my cock, all the while exploring my mouth with her tongue. "Today, we're gonna teach you about sex. Let's go." She grabbed my hand and led me out of the pool with Deb following us.

We walked inside and Deb went to the bathroom and came back with a few beach towels. They told me to just stand there and they would take care of me. They dried me off from head to toe, then dried each other off. They then led me to their bedroom and told me to lay on the bed. I did and Tiffany mounted me in a 69 position, pushing her pussy down on my mouth. I could hear Deb by my ear telling me how to eat her pussy. My cock was rock hard, but she knew how to suck me so I wouldn't cum yet. After a few minutes, without even realizing it, I was in a 69 with her on my side. That's when I felt a slippery finger penetrate my ass. I was a little shocked, but it didn't hurt. Deb asked me if that was okay and I mumbled that it was. Then I felt a second finger enter me, and Deb started to finger fuck my ass as I ate Tiffany's pussy.

Being a 15 year old horny teenager I didn't last too long. I tried to tell Tiffany that I was cumming, but her pussy muffled my words. I started cumming and she started swallowing. She didn't miss a beat. After I was spent she kept sucking until I started to get hard again. She finally got off of my cock and turned to Deb and said, "Your turn." Deb straddled my belly and reached down and started kissing me. While we were kissing I felt one hand on my balls and another playing with my asshole. There's nothing like two women working in unison taking care of a horny teenager. Then lifted up and put her pussy on my cock and plunged down. Holy fuck that felt good. I didn't have to do a thing. She began to fuck my cock, and because I had just cum, It took a while until I was about to cum again. I told her I was ready and in a flash she was off my cock and had turned around into a 69. I came and she swallowed it all, just like Tiffany. I could also taste her cum in my mouth as she orgasmed.

That was the first of hundreds of time we fucked until I left for the Navy. I learned many tricks and techniques from them, so by the time I got an actual girlfriend I knew how to please her until she couldn't take it any more. Now I'm married for eight years, and still have a fantastic sex life. I owe it all to the two lesbian bitches across the street.

#4114

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I saw an ad for a man wishing to have someone come to his door and drop to their knees , unzip his pants and suck his cock. I was uncontrollably sexually motivated , and nest I was at a strangers house giving oral sex in a doorway. I was so aroused when he pulled me inside , my mouth full of his cum, to a bedroom. We stripped off our clothes and fondled each other as we laid on his bed. He brought my head make to his already erect again penis for more oral sex. I was amazed when he asked if he could use me for anal sex. I was even more amazed when I let him use my virgin ass

I have never considered myself to be gay so, I use the more comfortable term I proved to be bi-sexual.. I also admit I saw the flashing red light of a video camera shining though the partially open closet door. I have never seen the video but the thought of one was so erotic !

My sin remains a secret until today

#3006

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Yes I am. My grandma and I made love for the first time years ago. After my grandpa's funeral I told my parents that I will stay with grandma for a while. I was 16 then and my grandparents lived in the same part of town. so I just got some clothes and my school utilities and moved in with my granndma. she has been 64 then and because of my grandpa's really unexpected death, she was very depressed. IT happened in the 3rd night. she came to me in the guestroom and begged me, to sleep near her in the large bed. She really missed my grandpa. We hugged a lot, but nothing more. But at being 16 I for sure got hardons. Sure she's quite old but my cock at that time was only interested in Tits. And my grandma had some. In the middle of the night I woke up because of someone's hand on my cock. She did not realize it, I think, because ma grandma still snored next to me. I tapped her on the shoulder but she did not wake up. So I layed back on my pillow and concentrated on her hand and my cock. I never imagined my grandparents still having sex at their age. But she knew what to do with a hard cock. she jerked me off like an expert and I did not last long. When I came down from my orgasm, I looked in my grandmas eyes. she apologized again and again until I took her and hugged her. She had started it in her sleep (or dream) and woke up in the moment she brought me to squirt. She has been shocked about what she had done and it cost me a lot of work, to calm her down. Finally I took her hand and put it again down on my cock, which again was hard then. she got big eyes and then even got a red face. but she did not take her hand away.

The next night I went to her room, when we went to bed and layed down beside her, without her coming and get me to. She looked at me, but then she smiled. For a while we layed there just hugging and she told me she needed that. then after a while her hand went down to my hard cock. this time she was awake and she nevertheless jerked me. I again came over her hand and she did not do anything to wipe it off. we layed there for a while, then sie asked me if I ever had sex with a girl. I had not and I told her. Suddenly she started rummaging and then, she apologized again and climbed on top of me. She's just tiny and it was no problem for me, but then she suddenly took my still hard cock and sat down on it. It lasted a moment until I realized what happened. I was inside her. later she told me the rummaging before was because she had to take off her pantie and because of her age, she had to put some oil in her vagina to become slippery. That night I had my very first real sex.

In between I am 32 and my grandma just became 80. We've had a big Party and although I'm married, I stayed the night with her and we've had a night of hot and dirty sex. My wife knows about our past and she's ok with it. She even watched some times (when we visit my grandma) and she even masturbated while watching but she does not want to join in. It's ok with me.

Lars from Copenhagen

#2985

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The first time I sucked another cock was when I was 22 years old. My wife was at home and I was on leave from the service. I met him at a bar. He said he was the owner of the bar. I sat at the bar and ordered a beer. He gave me the beer and asked if I was in the Army. When I said yes he said that he loved sucking soldiers's dicks. I was taken back and he asked if I ever got my dick sucked by another man. I told him no. His bar was in the basement of the hotel I was staying in and he told me to go sit at a table and he'd buy me a drink. Four drinks later, rum and coke, he asked if I was ready to get my cock sucked. After a couple more drinks on him and him asking again I decided that since I had never gotten a blowjob from another man I agreed. He told me to go up in my room and get naked.

About five minutes after I got back into my room he came in. He locked the door behind him and walked over to my bed. I was laying on the bed naked and he pulled me so my ass was hanging off the end of the bed. He knelt down and immediately put his mouth on my half-hard cock. He sucked me hard then put mu whole cock in his mouth. I warned him I was gonna cum and he shoved a g\thumb in my ass. That took me over the edge and I filled his throat with my cum. He took it all and sucked me as clean as a newborn fucking baby. He then got up and started to leave. For some reason I asked him if he'd like me to suck his dick. He said yes and immediately stripped. He was very fat and had a pretty small cock but when he laid on the bed I pulled his ass off of the edge of the bed. I bent down like he did and took his cock in my mouth. I felt his foot rubbing my cock and he kept asking if sucking cock made me hard. It did but I just kept sucking his cock. My cock was hard by the time he was ready to cum. His cock was small enough to take the whole thing in my mouth and he asked if I wanted him to cum in my mouth. I mumbled yes and kept sucking. He started cumming and I swallowed every fucking drop. My cock was never so hard, not even with my wife.

Ever since then I've been looking for cocks to suck and have even become quite the cum whore both in my mouth and in my ass. I love being fucked in the ass and having a large thick cock spreading my asshole out as I was being fucked. I've sucked more cocks than my wife has sucked me or let me fuck her. I've discovered another man that is willing to suck cock is insatiable and being bi-sexual I can now get all the cock I want in both my mouth and ass and I can suck all the cock I want. I'm still married and she has no fucking idea. I love her dearly but crave more cock than I ever thought I could handle.

#2840

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When I was 6-8 years old my mom would babysit a classmate of mine named Jesse. Babysit is a loose term, really my mom would be home for us after-school and would be gone all evening until about 10 minutes before Jesse's mom would pick him up. It was just me, Jesse and my little sister in the apartment most evenings for hours alone.

As boys will do, we some how ended up with our dicks out, comparing. What started as show and tell, quickly became touching, stroking and eventually sucking. We found my father's penthouse and hustler mags and just copied what we saw. We were both very small, both uncut and both ridiculously hard for boys that age. We kept it up for months.

Jesse would always ask if my sister could play with us too. I usually said no as my sister and I had some light play at this point and I was both embarassed that she would tell Jesse that she and I had already been touching and tasting and he might tell someone, and worried that adding another person to mine and my sister's play would increase the likelihood of someone saying something and us all getting in trouble and the play stopping.

On the few occasions I would get my sister to play with us and mimic the things we'd seen in hustlers and penthouse magazines, it was fun. No penetration, only hands, mouths and rubbing up against. Usually though it was just Jesse and I playing with each other, while my sister was in the livingroom.

Jesse and I eventually fell out of touch after my mom stopped babysitting him. My sister and I continued to play with each other, a lot until she I was about 12. We tried actual penetrative sex a couple times, but couldn't figure out the mechanics of it at that age. My sister and I aren't super close, but we're cool. No one ever found out about me and Jesse, or me and my sister.

#2816

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My wife and I have been together for 8 years. We love each other and have a fantastic sexual connection. We try EVERYTHING. We are fully open with one another about everything, except I was hiding a secret.

I've always known I was bisexual, but because of the small town I grew up in, I never acted on it. We now love in a major international City.

We were going through a pretty heavy swinging phase a year ago(we go back and forth on it) when she told me she would like to try one of the ladies only nights, which got us talking. I admitted I was at least curious and would like to try playing with men. She was intrigued, but a little apprehensive. Eventually she told me I HAD to go to one of the local bathhouses to have some fun.

That first time I got groped and grabbed by soooo many guys. (I'm reasonably attractive and toned). It started as soon as I entered the showers. All eyes were on me. It was intimidating, but so arousing. Next I visited the foam room and made out with a guy and stroked his cock a little bit. My first time ever touching another man's cock. It was smaller than mine but probably the hardest dick I've ever encountered. He started to finger me a bit and tried to fuck me against a wall. It was a bit too soon for me, and no condom means definitely no play. So I got out of there.

Next I visited the dark room and did some cheeky groping and stroking. Then I found my spot in the gloryhole rooms. It turns out I fucking LOVE sucking cock. I didn't even realise at first but I was moaning so loud and I was so hard sucking these guys off. A few guys stopped before coming and tried to enter my booth for sex, but I was enjoying myself and didn't want to stop.

That first night I sucked off 6 guys. It was incredible and life changing. I eventually went to the other side to try getting sucked off by a guy. It was completely different from a blowjob from a woman, but good, I still prefer doing the sucking. I eventually started to cum, and tried to pull my cock out of his mouth, but he sucked harder and made me cum in his mouth.

Since then I go once or twice a month, my wife is completely supportive and likes to hear how many guys I played with and how much fun I had. I still do the have sex with men(anonymous is a bit too dodgy) but my wife has purchased a harness and a bunch of compatible dildos of different sizes and has completely fallen in love with fucking me.

My wife and I still occasionally swing, I still play with women and I'm definitely not gay. But I am 100% bisexual. Sex with men or women is fantastic.