NSFW First Time Bottoming

Discussion in 'NSFW Sex and Adult' started by Austin MD, Feb 16, 2019.

  1. Austin MD

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    Many of you know my journey of being with guys over the last few months and my rendezvous with my coworker bae (who we are going to refer to him as Dame). Well I shared with you all that I am spending the weekend with him. He’s actually helping me tell this story to lol.

    So anyway, me and Dame been having some serious fuck sessions the past couple of weeks. The last few times we’ve been at it, I’ve noticed Dame has been getting a bit handsy and playing around my ass. He did informed me that he’s technically versatile so I already knew one day he would want to fuck me. So earlier today we were about to go at it again. We’ve been drinking all day, lounging around and horny. Dame flat out said “let me fuck you!” I don’t know if it was the drinks or what but I agreed.

    Mind you I have already heard of the horror stories of anal sex but I’ll admit I kinda dabble with it even with my ex girlfriend. I didn’t let her use a strap or anything but there were times she fingered me and I also used a 2 inch butt plug a few times so this wasn’t the first time anything went up the back door. So I got up and showered and used douche. (Sidenote: douching is really a mood killer when you are like ready to go now lol). After the clean up, I was kinda hoping he would have move on from me getting fucked but nope he was already game. I let Dame know the deal that this is my legit first time and his ass better be patient with me or I’m going to literally punch him in the face. He grin and said alright but I knew the mf’er was lying.

    So I am going to bypass the foreplay shit and get right into it. He had this numbing lube and put some on my ass. It tingled me but I was so nervous and my heart was racing. He finally put some lube on him and position his dick to my hole. His initial entry didn’t feel bad at all. It just felt wider that my little butt plug. He asked how I was the whole time. Then I got a little impatient and told him I’m ready for him to put it all in. He did asked a couple of time if I was sure and I said yes. He did and when I tell you I let out the loudest yelp. Just imagine a crying goat. Or when Castro bottoming. That was me. He was smiling the entire time too. I did have moments when i enjoyed it. Like I don’t know if I was was turned on by knowing another dude just as masculine as me in me. It just did something to me. Bro I was sweating and waiting for him to be done.

    It seemed like it took him forever to cum lol. Then he just laid on top of me for a while. I have gained a new respect for both him and others who do this shit regularly. It really takes a lot of concentration. It is a humbling experience hahahaha. Like I was so worried the whole time about the obvious but I see that he didn’t stop so I guess I was good. You couldn’t have told me I would have ever did this even a week ago but here I am. I think every guy once need to experience this (even though I know a lot are going to decline lol). I wanted to know from others how were their first bottoming experience and any tips for me in the distance future (if I decide to do this again).

    99DC99E6-5755-43C3-B7FC-7A6DA4BE834D.jpeg
     
    #1 Austin MD, Feb 16, 2019
    Last edited: Feb 16, 2019
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  2. takeyourmeds91

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    You can write the hell out of some erotica..

    Anyway, look at you! I feel like yall just found out about each other like last week lmao. I'm glad you've enjoyed your time on this trip (and hopefully there was some condom use, hmph)

    I'm not too big a fan of being on the receiving end so I have no real stories to tell - maybe that'll change with the right one. At any rate, I salute you stepping outside of your comfort zone and also sharing with us.

    P.S. your ex-gf was pretty open...she must've been something else other than black hahaha

    P.S.S. - *smirks* whose booty is that up top?
     
  3. Austin MD

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    @takeyourmeds91 To answer your question, we were safe. And you are right me and Dame been with each over consistently since last Wednesday or Thursday so a little over a week. It was bound to happened if you seen my other posts about him. And shocker, my ex gf was black. You’ll be surprised at what some girls are into especially when you’ve been dating a while lol.
     
  4. takeyourmeds91

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    You answered my P.S.S. in my last reply too btw lmao
     
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  5. ControlledXaos

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    A lot of guys pre-prepare so it's not sooo much of an issue but yeah. If it's spontaneous, this just comes with the territory. Everyone involves understands with experience and patience.

    Yeah... I could have told you that that was NOT gonna happen.

    :franko1::dead1:

    Yeah... This is why I usually start on top. That way I can control the speed of entry. After a little bit of this, I'm good and we can change positions. But it usually is a thickness issue than length issue for me. If a guy isn't super thick we can actually get right to it. I just prefer to be in control of the initial penetration. I have a squat butt so sometimes, dudes just be too ready to go and I'm like..."Woah, hoss! Not so fast there!"

    100dap:mynicca:

    Letsnottalkabout my first time. But I'll just say that I wish I had had resources and people to ask.

    As I mentioned above, starting out with me on top works 100 percent of the time. Most guys don't know how to pace themselves on that first entry. That is problem I think that prevents many guys from even trying it. I think one time is not enough. As many people just have bad first times.

    I have not bottomed a lot lately so I'm usually really tight and it just takes my body a while to dilate so we can get it in. Once you relax and get into it, it can be really good. The nutt you catch is awesome!

    I think the main thing is to be clean because that helps you not worry about any accidents. Even though going to take care of that can seem like a mood killer, it just has to be done. If you're the top, it may seem like an eternity for dude to come out of the bathroom and ready tho. lol But man... get you a flip flop going on and OHHHH MYYYY GAAAWWWDD! Man... being verse is awesome!
     
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  6. Austin MD

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    Thanks man. Well I was initially going to squat on him but he suggested for me to lay back and he’ll ease in me. I can’t complain too much about my first time with bottoming and if I ever get the opportunity to sleep with a bottom I’m going to make sure they are well taking care of because it’s a real delicate experience.
    It’s still a lot to digest that I let some guy fuck me. Next time I’m definitely going with my instincts to squat down like you said.
     
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  7. ControlledXaos

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    Well yeah .it's definitely intimate to have another person inside you. But I think it says a lot about how secure you are that you can submit to being penetrated and still not be submissive. I'm throwing it back like I'm fucking the dude. Lol like in my mind I'm like "knee grow, I'm finna MAKE you nutt." lol

    There's a certain amount of self assurance that comes with being masculine and able to bottom. I think it's sexy.
     
  8. Jai

    Jai I'm honing in on my inner freak.
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    Aww. Well, I douche every so often but not for sex, just for colon health. I'm the picky type...I used to be pretty shy. Still a little but ever sense I was fucked for the first time I've been bolder.

    Pretty selective but I'm like shy until I get in the bedroom and I will surely mutter Fuck me, fuck my ass, that's all you got nigga or anything else I feel like talking shyt about..

    Anywhos, Idk about the squatting on peen. I seem to be in love with doggy or missionary. Doggy just to look back at the guy cuz they be sexy behind you and missionary so you can grab onto their booty. I love muscle butts. Hahaha.

    Did you get that feeling like you had to pee? My first time was like that. It felt like I wanted to pee. I suspect his was hitting my prostate and I was gonna nut maybe? I would love for a Top to smash me like that & make me cum with no hands..but you know how most of them are..you start moaning and saying they name...they be looking all cross eyed and two minutes later.."You gonna make me nut!"

    Huh?!?! What you mean?!?!

    I was told squatting on the peen is best (easiest) but I'm not a fan of it tbh...If I did it, it'd probably be turned around so your butt is facing him. I saw it on a porn and you just know how Tops are... *rolls eyes*

    I guess it does depend on his size .I'm a small person, 140 and most guys that I've been with have always been taller. I'm usually bigger than them dick wise but the last guy was about maybe 5'11- 6-1 and he had a nice dick that was bigger than the pic I saw. The first guy was big too and I asked him what he thought he was doing with that.

    Is that your ass in that picture? I know Tops be having nice asses too. I love messing with Tops butts.
     
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  9. Austin MD

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    Honestly I felt like I was gonna shit. I could’ve deal with the pee feeling more. And yea I made Dame cum with no hands and that was sexy. That’s low key a goal for me too lol!
     
  10. OckyDub

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  11. OckyDub

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    I'm too drunk and immature to deal with this thread right now...

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    #11 OckyDub, Feb 17, 2019
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  12. Jai

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    You're always drunk...:comeon:
     
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  13. OckyDub

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    Damn...shit just turned into an after school special

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  14. Jai

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    :maxine:
     
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    Congrats on having a positive first bottoming experience. In my current relationship I top most of the time. Every time I try to bottom for my boyfriend I just can’t get into it. I’m able to get past the pain and relax but there’s an absolute absence of pleasure. I like seeing him happy but I just wish I enjoyed it more. It’d make it easier to get through
     
  16. Winston Smith

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    I bottomed a couple of times for the last dude I was with. Wondering, barring STD concerns, how do y’all feel about bottoming and having a dude cum in you with or without the condom? Some dudes like being “flooded”, others don’t.
     
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  18. SB3

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  19. Omega Level

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    Great story. Look at you breaking a gay rite of passage. Seems like you were definitely more savvy than my first time.

    For the sake of not being long winded let me give you the abbreviated version as much as possible -

    I grew up in the south. South Florida to be exact. Ft. Lauderdale. Always knew I was gay, but was completely oblivious to any sort of gay world around me. Not a popular thing to be in the black south. Upon graduating high school and going to college in Atlanta, I again had absolutely no idea of Atlanta being a gay world mecca. About 20 years old. Working on campus. Fellow campus co-worker that was an older student that came to college late. I think he was about 26. Very attractive and masculine. Would flirt with me and I just thought he was corny and played too much until I accepted his offer to come over his place to chill and watch a movie (very pre netflix). I was unaware that gay man can be masculine. Again, naive southern boy thinking to be gay you have to be a queen. 30 minutes into watching the movie, he leaned over and kissed me, I froze but tried to kiss back. I'm sure it was a very bad attempt. He got the remote. Cut off the TV and ushered me to the room. I was shaking but wanted to go. Got nude, oral, he put on condom, put something that felt like gel in my ass hole that was cold as fuck, got on top on me, and I felt the worse pain I ever felt in my life. He couldn't finish of course so we just did frottage. (side note - his dick wasn't even big either. just hard as fuck)

    Went back to the dorm later and went in the bathroom thinking I had to shit and the pain was so unbearable from the mere attempt of him trying to fuck me, I cried on the toilet. Not a good first experience.

    Afterwards, my best friend (which I kinda knew) came out to me as gay. I told him I was too. We got an apt together. Did our first gay clubs. Met all kind of gay men in Atlanta. Got my Atlanta black gay education from the EXPERTS. And the years that followed, lets just say I was able to due squats on that future peen.

    Tips? It's many tips I can give about bottoming in general. Prob too many. So the main tip I would say is, be sure you are committed to doing it. Its ok not to bottom if you don't want to. Because there is nothing worse than a dude that really doesn't want to bottom. It shows in every movement. As a vers, I have committed to being good to great at both. Convincingly enough where I have been told its hard to know what I like better. But bottoming isn't for punks. So if you giving up that ass, be sure he can GET THAT ASS!!!
     
    #19 Omega Level, Feb 17, 2019
    Last edited: Feb 17, 2019
  20. Infinite_loop

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    glad you had a fun weekend with ol' boi. I have bottomed once in my life. It was terrible and there's nothing else to say about that lol I definitely have tremendous respect for the dudes who bottom on the regular. The physical and mental prep alone is a lot, but who knows maybe one day(soon) I might decided to take some lessons :nerd:. A verse situation would be dope; I hate feeling limited within my sexuality.
     
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  21. Jai

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    This is a good time to insert a [wait, there is a such thing as a Total Top] thing somewhere oh and [there are way too many bottoms] in this gay lifestyle.

    Oh, I laughed when he said he felt like he had to go shit. It's so interesting how some guys turn into the biggest women when penetrated. Hit that high note Mariah, some guys say they feel like they have to crap & some dudes hit the Jenna Jameson.

    You know I like to overanalyze..(haha anal)...things & I find it real interesting hom some men like to Top. Like the whole dominance thing. Some animal planet type stuff and alpha males. I'm learning more about these alphas. I didn't even know they had freaking levels of submission for a male. They had a picture thing on one site I was reading and I was like..huh????

    You would call me a lazy bottom since I don't like to ride or squat on anything like that.

    Hey OP, do you get that booty sensation now. It's this feeling you get when you want dick. It's not like being horny...well it is but it's like your buns are like I need to feel a dick up in me...kind of thing. It's strange. Like you know how you can look at some dudes and be like, "I'd let him fuck." Kind of thing and you feel this sensation. What is that?!?! Bottom's Spidey Senses tingling? Hmm.
     
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  22. ControlledXaos

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    The best advice I can give someone is to diddle around and find your prostate. If that means going to the dirty bookstore or Amazon and getting you a toy to assist with it go ahead. There's nothing like that nutt when that p spot has been stimulated.

    As Y'all knows I'm not big on huge dicks so the toy I got was a little thinner than most men. Mainly I wanted to find my spot and focus only on it and not the feeling of fullness. This is what worked for me after 3 LTRs. Because I too was just bottoming out of duty. Yes I wanted some ass but I was okay with playing for it by tooting up myself. And it was good. Don't get me wrong but after I did some digging around on my own bottoming is a lot more pleasurable because now I know what I'm looking for. Similar to how some women never orgasmed before they got a toy themselves.

    As for going up a few octaves, I have a deep voice so me going up isn't about to break no glass but you can definitely hear a weakness in my voice. I own it. There's pleasure in being dominated too. I have never felt like I was man's bitch though. Trust and believe that he had some octave drills with me on top too.

    I think sex should allow one to escape and let go. If it gives you pleasure and doesn't hurt any more else then go for it. If getting your hands tied behind your back and being "forced" to take it is your kink, catch that nutt and forget what other mofos got to say about it.
     
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  23. takeyourmeds91

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    Singing my life with your words

    Oooo @Rico , that's so personallll - lol sike nah, the thought it hot..again barring STD concerns.

    Three thoughts: Yall Miami/Lauderdale gays are a whole other species. You must have went to Morehouse *smirk*. Atlanta is probably the best place to get a black gay education lmao

    Two thoughts: Yall chronologically-mature mthfkrs be knowing shit. That's exactly what it feels like and I could never describe it, "sense of fullness." I don't like it at all. But you're right, it takes knowing your body and what to focus on. AND you're description was hot
     
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  24. Jai

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    Oh I ain't letting no man nit up in me...lol I know when I got fucked he was hitting something I felt that shit well..I was missionary like Halle Berry on the couch get fucked & it was my first time and I remember that feeling like I could feel him tapping something...and whatever it was..it still had my legs shaking afterwards, ass was sorta sore but it was nice sore? I had to soak in the tub...

    Like a few others in here, I'm one of those lucky bottoms and I know if my man ducks me right and with enough aggression and passion I will nut hands free for sure.

    Since I'm demisexual and sapiosexual..I ain't letting no nigga fuck unless I get to know him and he is intellectual. Once I get to know him and hang out AND I find out he's intellectual with a freaky side..I open right on up.

    It's always nice to hear others experiences though. I would want a toy but I like to feel a whole dam man. I wanna grab and feel on him..Lol.. that toy would irritate the hell outta me.
     
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  25. SB3

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    Outside of the concerns mentioned, I can't imagine why it would be a big deal. The pull out method was intended for preventing pregnancy, and we alrdy know our risk odds there.
     
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  26. ControlledXaos

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    Oh I forgot to to address this that ...

    I have came and bee cummed in before only in an LTR.

    It's hot, can't lie. And your body will react. I can definitely tell there's more product ejaculated when I I'm inside someone, raw. Now obviously I haven't had that happen in years but I know what it feels like.

    As far as being on the receiving side, afterwards I go clean up.pretty much a squash squash afterwards because I'm not going to sleep with nutt just hanging around inside of me.
     
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  27. Austin MD

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    It seems like everyone enjoyed my ass pic lol! But yeah, I cannot complain too much on my bottoming experience. It was fun, safe and I am glad it was with someone I connected with.
     
  28. Omega Level

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    A whattttt, How dare you sir!
    Correction - All Florida citizens are a whole other species not just us gays. :kermit::bronbad:
     
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  29. ControlledXaos

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    That is the damned truth.

    Floridians running around naked as they please eating mofos faces off. Y'all is crazy.
     
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  30. Krimsonic_

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    Any specific type of toy you recommend??
     
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  31. Infinite_loop

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    [​IMG]
    *Listening in* because I did try to by a toy at some point and it ended up being....um...let's just say "big" lol
     
    Boaxy, Krimsonic_ and ControlledXaos dapped this.
  32. ControlledXaos

    Squad Veteran Most Valuable Player The 1000 Daps Club

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    I made the mistake of getting one that was too big and poorly made years ago when I was out of a relationship but was soon going to start looking again and didn't want to look too virginal if I was going to hook up. While traveling from Texas one day, I ran into some dirty book store off of 20 in middle of Louisiana and got this realistic looking dildo. The length was fine. But the material it was made from wasn't too tenacious. Plus, it was made with a seam. That steam felt like it was cutting me. Even tried to put a condom on it to see if that helped but no. No matter how much lube I tried it was a no go. I honestly could not get more than the head in. I think I kept it for a while then one night just threw it down the street. I would have paid $5.00 to see who discovered it though.

    Everybody's body is different so keep that in mind.

    Well, I wasn't trying to have everybody all up in my business but, if this helps someone else, then it's fine. I'm a Scorpio so we know stuff. Whooo here it goes....but first....

    Shout out Amazon for making my purchases not appear on my "Your Orders" page. I had to search for my purchases. So feel free from shopping for this stuff in the comfort of your own home. Amazon keeps all that stuff separate. They the real MVP.

    Anywhooo....

    So I got two things. Unfortunately, the initial item I got was not available any more. It is small, thin specifically made for male anatomy prostate simulator by Aneros, the Helix. I was intrigued by the Pornhub videos of guys using it and losing all control of their bodies. I didn't get the one of their larger ones but I probably should have looking back. This helped but I found that I needed something with more 'hook' to it so to speak. I found what I was looking for on my body with it so it helped but I did not get uncontrolled gyrations. I can tell you that the nutt was a lot thicker. So... I eventually I was ready to step it up a notch so... I got this and it's fine. It is a good size for me range for humans and it's got a little bulb on it where it thickens up just enough to hit my P. Main complaint is the material it's made out of is nice and smooth but it needs a bunch of lube. The Helix let me explore better. so for discovery, thinner, smaller is better. The 'have to pee' feeling is what you want and then you'll be like 'Oh...THAT'S it' and you'll ooze out some. That's where you want to be.

    Doing some research on this, I ran across a Reddit, I don't know which one, I did not save it, where several guys were saying that one of these helped them find their spot because they could control it better while lying down. Stands to reason that it would by the looks of it.
     
    Boaxy, Krimsonic_ and Austin MD dapped this.
  33. SB3

    SB3 is a Featured MemberSB3
    Squad Veteran Most Valuable Player The 1000 Daps Club Supporter

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    Look at you, educating the chirrens on how to be solhos. It takes a village...
     
    Boaxy, Krimsonic_, Austin MD and 2 others dapped this.
  34. ControlledXaos

    Squad Veteran Most Valuable Player The 1000 Daps Club

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    It's a gift. I don't own it.
     
    Boaxy, SB3, Austin MD and 1 other person dapped this.
  35. SB3

    SB3 is a Featured MemberSB3
    Squad Veteran Most Valuable Player The 1000 Daps Club Supporter

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    I wasn't gonna post in here because I don't have much of a story. However, I remembered that although we had fingered and enjoyed that nut, it did pale in comparison to the first time I got THAT nut! Even as a top (I've bottomed for 2 guys in exclusive situations, and if I met another top I'd be open to a more verse relationship) I can def appreciate the prostate stroke nut. That said, as someone who needed extreme patience, I recommend laying on your side as a rookie.
     
    Boaxy, Austin MD and Winston Smith dapped this.
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