Guys - tell about the first time being fucked

[mtsnowrider]

Well, if you both enjoyed it, top, bottom, is there really any point to being pegged as type of something?

I don't mind being pegged.... And we did both enjoy it

 

[tristantrotsky]

My new boyfriend and I went up to play in the snow. Going home we were wet and cold so we got a hotel on the way down the hill. The clerk must have read us because she asked if we wanted a double bed. I said sure.
We showered, had food delivered and hopped in bed together naked for the first time. After a little playing around, he started probing me with his cock. I wasn’t too sure about losing my virginity, but there was no stopping him. He just took over which really turned me on. It hurt at first, but he kept going. Then after some nice fucking he pulled out. I was confused.
Then we made out for awhile and then he cleaned my dick and then sucked me off until I came.
When morning came we made out a bit and then he positioned me missionary style, and we kissed and kissed as he went in me. It still hurt at first but he was fucking me like a madman!
The pain was gone. It was fucking great. I’ll never forget his pulses inside of me, nor the special feeling of cum dripping out of me as he pulled out.

You sound delightful. That is such a wonderful story.
You are fortunate to find such a tender and considerate lover to take your anal cherry. That is such an important moment in your life, and you need it it be right.
I'm so very happy for you, Clint...

 

[Chi_Guy_68]

It hasn't happened yet (I haven't hooked up with any guys yet period), but I'm turned on at the thought of it... I want to experience how amazing it feels (at least according to those of you who've done it)

 

[Vitriolhack]

It hasn't happened yet (I haven't hooked up with any guys yet period), but I'm turned on at the thought of it... I want to experience how amazing it feels (at least according to those of you who've done it)

Well, as in introduction to the subject, you could, take matters into your own hands.

 

[Chi_Guy_68]

Well, as in introduction to the subject, you could, take matters into your own hands.

I am working up the nerve to play with a guy.... I will probably start with oral first though, before I get fucked

 

[Vitriolhack]

I am working up the nerve to play with a guy.... I will probably start with oral first though, before I get fucked

wishing you a pleasurable experience.

 

[Vitriolhack]

I don't mind being pegged.... And we did both enjoy it

I love a good pun!

Happy you enjoyed your kinky fun with your partner!

 

[Luganis]

My first time was with a transgender woman that I had been talking to for months but then met for a week together.

It was so exciting riding on the metro with her as she put my hand in her lap and I could feel her hard cock. There it was - would I be able to go through with it? What had I gotten myself into?

After we checked into the hotel and got to our room, we immediately undressed and began to kiss and play with one another. Finally I pulled her panties off to reveal her throbbing little cock. It was between 4 and 5 inches but really stiff and hard definitely ready for action. Seeing it made me realize just how much I needed it.

I wasted no time putting lubricant on her cock and a little in my hole, then I assumed the doggie position on the bed. Immediately she got behind me and I could feel the tip of her cock at the entrance to my hole. Then in one big thrust she shoved her cock completely up my ass!

OMG! My head was spinning both from the stab of pain I felt as well as the realization that it was actually truly happening. After so many fantasies over so many years, here I was bent over like a bitch with a cock in my ass. It felt unreal. Was this a dream?

After only a minute or two of vigorous fucking, she stopped her thrusting and pushed her cock in as far as she could go. This was the moment I had been waiting for. Hearing her moans and groans, I knew that she was having her orgasm and breeding me with her cum. I couldn’t feel it but it was the most sexually exciting moment of my life.

After she finished cumming, her cock stayed inside me and she leaned over me to say, “Don’t move. I am going to get hard again and fuck you some more.” Really? I could not believe what I was hearing but I followed her instructions and stayed in position with her cock still in my ass.

After only a couple of minutes, I could definitely tell that her cock getting harder and harder. Soon she was ready for round two and she fucked me again this time taking more time before cumming again.

As I was taking her second load of cum, I thought to myself, this is incredible! Here I am getting two loads of cum from this girl in a single fuck! God, she is an amazing fucker!

So she was. That night she fucked me three more times cumming in my ass each time. I felt like a wanton cock hungry slut but I knew then that I was born to be a bottom. All I want is a girl with a cock dumping her cum in my ass.

You reminded me of my first time. It was during a business trip in Brazil, I met this exotic girl, I knew she was trans but she looked so sexy and beautiful that I didn’t care. We started making out in the bar of the hotel, and before taking it to the next level, I was kind of scared, but she was too beautiful to let it pass. So, still sober I took this gorgeous TS to my room and she undressed me. I was steel hard. I wanted so much to see her naked, that her ministers didn't stay on long.

And there we were, her nice curved 6” but not too thick dick, and my 5.5” kissing each other while we were making out. It was surreal, this sexy woman with 34D tits and 6” dick, and so feminine, so sexy. I turned her, my dick was rubbing against her round hard bum while I was grabbing her tits and biting her earlobes. All of a sudden she turned, and she took control. She had me facing the wall kissing my neck, and playing with my balls when she started rubbing my rosebud.

She whispered “I will be gentle, I know is your first time”. She took my hand taking me to bed. She grabbed her purse, took out lubricant and condoms. She started spreading the lube and penetrating with one finger, then a second. She positioned me doggie sty took her 6 inches wood and started pressing.

”relax” but it was painful, “push like if you’re have to poop, it will relax you sphincter”, and effectively it happened, she’s slowly entered me. It was a strange feeling, I didn’t really feel pleasure. She started to fuck me nd still I wasn’t getting all the hype of anal sex. She came and I only came after she gave me the best BJ of my life. She stayed the night.

In the morning, she started rubbing my rosebud to wake me up. It felt really different. It was electric. She mounted me again. My sphincter still needed some help to get penetrated, but the feeling was completely different from hours ago. She fucked me slowly first and raised the pace. I was now in heaven. I guess her cock was massaging my prostate. I came without touching my dick. Fernanda came too. We spent more time relaxing. We spent all weekend fucking like rabbits.

I was sure she was an escort, so I was prepared to pay big bucks, but we had such a great time the whole weekend that she never brought the subject up.

I got hooked. I was definitely bottom with trans girls, and top with girls. Since then I’ve been with many others, it’s never like that weekend, but when I spend a long time without enjoying nice trans dick, my body begins to demand it.

I’ve never been with a man, and I am simp not not interested not attracted to men…

 

[Escierto]

You reminded me of my first time. It was during a business trip in Brazil, I met this exotic girl, I knew she was trans but she looked so sexy and beautiful that I didn’t care. We started making out in the bar of the hotel, and before taking it to the next level, I was kind of scared, but she was too beautiful to let it pass. So, still sober I took this gorgeous TS to my room and she undressed me. I was steel hard. I wanted so much to see her naked, that her ministers didn't stay on long.

And there we were, her nice curved 6” but not too thick dick, and my 5.5” kissing each other while we were making out. It was surreal, this sexy woman with 34D tits and 6” dick, sand o feminine, so sexy. I turned her, my dick was rubbing against her round hard bum while I was grabbing her tits and biting her earlobes. All of a sudden she turned, and she took control. She had me facing the wall kissing my neck, and playing with my balls when she started rubbing my rosebud.

She whispered “I will be gentle, I know is your first time”. She took my hand taking me to bed. She grabbed her purse, took out lubricant and condoms. She started spreading the lube and penetrating with one finger, then a second. She positioned me doggie sty took her 6 inches wood and started pressing.

”relax” but it was painful, “push like if you’re have to poop, it will relax you sphincter”, and effectively it happened, she’s slowly entered me. It was a strange feeling, I didn’t really feel pleasure. She started to fuck me nd still I wasn’t getting all the hype of anal sex. She came and I only came after she gave me 5he best BJ of my life. She stayed the night.

In the morning, she started rubbing my rosebud to wake me up. It felt really different. It was electric. She mounted me again. My sphincter still needed some help to get penetrated, but the feeling was completely different from hours ago. She fucked me slowly first and raised the pace. I was now in heaven. I guess her cock was massaging my prostate. I came without touching my dick. Fernanda came too. We spent more time relaxing. We spent all weekend fucking like rabbits.

I was sure she was an escort, so I was prepared to pay big bucks, but we had such a great time the whole weekend that she never brought the subject up.

I was hooked. I was definitely bottom with trans girls, and top with girls. Since then I’ve been with many others, it’s never like that weekend, but when I spend a long time without enjoying nicke trans dick, my body begins to demand it.

I’ve never been with a man, and I am simp not not interested not attracted to men…

Good for you getting hooked. Not too many guys just decide to let it happen and go with it.

 

[Luganis]

while I look the same, my needs changed completely. I enjoy topping women, but I need to be taken. My favorite, very feminine tras girls, but I began to enjoy letting dominant women peg me…

 

[mrdiscreetshh]

does one of those fuck machines count? If so, oh my!!!

 

[Filipinawife]

I have been described as a LBFM

 

[BatherinMichigan]

I had always messed with my ass with toys, always wanting the real deal, when it finally happened, just thinking "This is happening this is happening" and it happened, and I loved it.

Exactly! I got hard reading your brief post.

 

[LeeKee]

I have been described as a LBFM

Forgive my ignorance, what is LBFM?

 

[Filipinawife]

Forgive my ignorance, what is LBFM?

Little Brown Fucking Machine

 

[LeeKee]

Little Brown Fucking Machine

Oh ok….omg! Pretty hot!

 

[Travler99921]

I met with a guy in his hotel room. After a bit of play he told me he wanted to fuck me. I surprised myself by saying yes. His cock was average length but thin. I was sure I could accept it inside me.

He entered me and it felt good. He didn't cum, but eventually he pulled out. After chatting a bit he got hard again I asked him to fuck me again. This time he came into a condom. It was very exciting knowing that I made him cum.

After we were done I felt a bit feminine. I actually liked the feeling. I have never felt fully masculine again.

 

[tristantrotsky]

My first time was painful. Even though he was being patient and going in a little at a time. I kept telling him to pull out because it hurt. Finally he suggested I get on top. I did and even though it was still painful I was determined to have him in me. I eased down on him gritting my teeth. When I finally felt it break the plain of pain it slid in nicely. It was sexy to hear him say ahhh there it is. I sat still for a moment to become comfortable with his cock in me then began to ride him. It was bliss.

I feel for you, I really do. That first time taking cock is such a major step, but having a patient considerate friend is so important in making it a good positive experience, and your determination to take it all does you proud. I'm sure you've enjoyed much satisfying fucking since then...

 

[BrokenQuill]

I was lucky that my first time was with a considerate friend. He wasnt huge either, so that helped with the anxiety side of things. He spent a lot of time rimming me and finger fucking me before finally entering me. By the time he slid his cock into me I was so ready for it that he slid in beautifully. The feeling of him gently thrusting in and out will be a memory that stays with me forever.

It was only surpassed by the sensation of his cum dribbling down my inner thighs later on.

 

[Harley55]

After years of playing with but blogs and dildoes, had my first experience getting fucked with a guy I met on Silverdadies. Was amazing. That was 8 years ago. Since then, I can’t get enough. He is a buddy I continue to see a couple times a month. I can take a pretty big cock in my ass or throat with no problem. Best is getting fucked while sucking cock.

 

[Catbit20]

Years ago I was having a bi mmf oral session with a bi couple.

We both fucked her but, I wasn't ready for anything up my ass (so I thought).

Things got hot & heavy, they had me folded over with my head down on the bed with my ass up & legs spread.

She was rimming & tongue fucking my smooth, shaved ass while he licked my shaved balls & swallowed my 5.75 inch cock.

As they were about to make me cum, she slid a long, thin dildo up my tight ass.

That made my balls explode shooting cum all over his face & lips...

They kissed sharing my cum as I lay under them recovering.

He then put his hands behind my knees pushing my legs toward my head.

She sat on my face giving me a great view of her shaved pussy and ass. I of course began eating her pussy & rimming her ass.

I felt him put his cock on my asshole & then felt him slowly begin to push in.
I felt some pressure as his cock went up my tight ass.
The lube from the dildo fucking made my ass easier for him to slide his cock in.

I didn't protest & instead let him fuck my tight, shaved ass.

luckily his cock was only about 5 inches long, so it wasn't too hard on my virgin ass.

She stroked & sucked my cock as he pounded my ass until he unloaded cum all over my shaved ass, balls & cock.

They won me over!

 

[Luganis]

I’m sure that was the first of many others, and you got totally hooked

 

[AppleCucumber]

I've told a few people here this story, it was my first and only MMM threesome.

Even now I don't always like taking it in my ass, just when I'm very horny. I'd sucked a few cocks but my next fantasy was sucking two at the same time. There was this couple I was chatting to about it and they invited to come and have fun. After some small talk they pulled out their cocks and guided me to me knees. Their cocks were average size, one slightly longer. I was alternating between them for a while, sucking one while stroking the other. I asked if they could fit both in my mouth, they did with a struggle.


They took their clothes off and asked to me to stop teasing them and show my ass. Then for me to take off my shirt so I don't get any cum on it. They were getting super turned on and started fucking my face. We moved to the couch, and they forced me to deep throat, they kept getting rougher. I felt a finger in my ass, and it felt so good. More fingers were added and I was getting finger fucked. I did try protesting but my head was forced to take a cock all the way. It was actually so hot being dominated by two men I didn't think previously I would be into that.


The fingers left while I was sucking on the longer cock. I felt a hand pulling my ass cheeks apart and then the tip of his cock push against my virgin asshole. We didn't talk about this, or the finger fucking, but I was too busy to notice until his head pushed inside me. He slowly slid until his balls were against me. I tried moaning but my mouth was full. Eventually he was fucking me, I was being fucked from both ends. I was a complete slut for cock, being spit roasted is something I'll never forget. He came in my ass and told his bf to try out my ass. He didn't take long to cum too.

We talked after and he apologized for going further than we discussed. I said it was fine I didn't know I was ready for that but I loved it. Unfortunately we didn't meet again, I'm always looking for a hot couple to submit to.

 

[AddyB]

I really want to get fucked by another guy. What’s it feel like the first time?

Me too! I need a man to fuck me! Please!

 

[JudyCD]

First time I was on my hands and knees. It didn’t hurt but not as good as I expected. Later, I found if I was lying on my tummy with a pillow under my hips, it was as good as I hoped….better actually.