First time bottoming
So a quick download of background info
I was married and a swinger for a long time.
Towards the end of the marriage I discovered I was bisexual and since then have been trying to explore more bisexual experiences mostly with couples.
(I have a few stories of that posted on my page)
Well about two months ago I had finally convinced a bartender at my local lgbtq bar to go on a date with me. I had been going there for a while to try and maybe meet new people. It hasn’t really generated much but me and this bartender built a rapport.
She is a lovely person. I find her very attractive. She is trans and was not born female but is extremely fem presenting. Well call her Amber for this story.
I had asked for her number at one point, she declined but had me add her on Instagram.
This allowed me to at least interact with her from time to time and eventually get her to let me take her on a date.
Fast forwarding, we get to a point where I tell her about my swinging/slutty past. I was worried this would be a deal breaker but she seemed to have more and more questions about it.
We end up hooking up. Pretty standard hook up.
I don’t bottom. I’ve had my ass played with, never really enjoyed it. I have and like sucking dick that’s not a problem but I’ve never taken a dick anally.
This wasn’t a problem for Amber at first……
Amber is 5’4” ish, has a wolf cut that’s half black half blonde. She’s African American. Septum ring. Tattoos Pierced tits that are small and cute. She has been on estrogen for some amount of time. Has an out of the world ass. And has the biggest dick I’ve ever had in my mouth. Like had to get better at sucking dick just for her lol. It was a bit intimidating. It’s actually the only person I’ve hooked up with that has a dick that’s almost as big as mine.
The first couple times went basically the same way. Starts with heavy kissing and groping till I start taking off her clothes. I suck on her tits and move my way down to her cock. I tease it. She has small balls but I love kissing them and even eating her ass. As she’s grown more comfortable shes has started grabbing my head and actually fucking my mouth with I’ve never had done time before. Even holding my head down till I gag.
I’ve only been with purely submissive partners with cocks. It was shocking for me but I did like it.
Eventually we’ll switch to her sucking me or we sometimes 69 but I make sure she gets more oral since it always ends with me topping her.
Another new thing, she can’t always cum. I guess the estrogen starts to mess with that. I do kind of wish she did still cum. She’s the only one I’ve fucked anally and can’t get to cum from it. Hurts my ego lol. She sometimes will kind of cum but it’s not a lot.
But she has came in my mouth. I’ve never had dick cum in my mouth before her. It’s only happened twice, but the first time I gaged, and as I took my mouth off a tiny bit shot right over my eye/eye brow.
I couldn’t believe that a little over a year after finalizing a divorce I was on my knees sucking dick and had cum on my face lol.
She gives me warnings of a “possibility” of cum now. But I did manage to keep it all contained the second time it happened and she made out with me while the cum was still in my mouth. Which made me feel super slutty but the passion she had, the way she bent and reached down grabbed my head and brought me to her mouth was so fucking hot.
So we’ve been seeming each other multiple days a week now. And she has started to express wanting to top me. And how it’s a little unfair that I get to top her but not the other way around.
I tried not to be selfish but honestly was super hesitant and I didn’t really want to.
We agreed to start small and start with smaller toys.
First it was us having our normal routine but she slipped in a butt plug while sucking my dick and then I’d fuck her with it still in me.
This did make sex feel better for me, but hated it the moment after I came lol. I didn’t want it there anymore and felt annoyed I had to give effort in getting it out.
But for her I would keep exploring a little.
She bought a new toy for me. Invited me to her place.
When I arrived she brought my right to her couch. Sat me down and told me to get naked. She takes off her comfy clothes and has black lingerie on. She goes down on me and is sucking my cock. She scouts me closer to the edge of the couch and lifts my leg some. She starts eating my ass. Then I feel her lube it. As she sucking I feel/hear a vibrating toy starting poking my ass. It doesn’t go in right away I kind of tense up. She tells me to relax and starts deep throating my cock and I feel my ass open to her vibrating anal bead type toy.
This is intense. It’s like the inside of my cock is vibrating. I’m letting out moans I’ve never made before. It’s like a whole body high. She’s slowly putting more into me. I can feel when a new bump/bead gets inside me and my whole hole recloses up around it.
I ended up exploding. She’s trying to swallow it all but between my convulses, and never ending cum it’s pouring out of her mouth. I can feel it dripping down my cock, all while my ass is pulsing on the toy.
I’m telling her to take the toy out but she’s loving this and she’s still sucking and putting pressure on the toy teasing me till I completely tap out.
I will say once the orgasm ends, I hate having to have what ever is in my ass taken out. I’ll never enjoy that part lol.
So we explore with that toy a few times and finally agree to let her fuck me. I was surprised on how different she felt compared to the toy. The toy made every thing vibrate and feel “full” her cock made me feel “open” like even if she took it out I feel like was open. But the real difference was feeling it deep inside me. It felt like the tip of her cock was touching my stomach and the base of my cock at the same time.
It did take some effort for her to get into me. But I was bent over ass in the air. She was standing on the floor at the edge of the bed. Grabbing my hips, slapping my ass, calling me a “good boy” it was a such unique euphoric feeling. I can’t come from it unless she’s jerking me off at the same time. But she took my anal cherry.
I’m learning how to be on top with her inside me now. I don’t really enjoy being on top but doing it for her enjoyment.
I still top her way more than she tops me but I am regularly taking cock in the ass now.
And sometimes I’m the only one getting topped in a session.
Recently I took her to the local swinger club. We didn’t have a goal of swinging but just wanted to show her it since she was interested. She got to dress slutty and be half naked around other half naked sexual people. Got to mingle. We fucked in a room that people could watch and a lot of people did.
But now she wants to top me while other people watch. We’ll see lol.