My new trans GF loved Haulover beach in Miami she said it was so freeing to not tuck her cock and just let it hang free with no tan lines. I was hesitant to go and then she offered me an incentive. If I go and don’t love it she will let me fuck her ass.

She had never let me fuck her sexy ass so of course I said yes. She said great let’s go Saturday. I however had to work Saturday morning. She told me to do public transportation to work and she would pick me up. It sounded like a great idea.

Saturday am we both woke up as I was about to get out of bed she grabbed my hand and placed in on her morning wood. I said babe I gotta shower and get ready. She said you don’t have 5 mins to help with this? I said maybe 5 mins. She said then let me kiss you and pound it out baby and climbed on top of me. I wrapped my legs around her waist as she spit on her hand and slide a finger in my ass. Then I felt her tip at my hole as she spit on her hand again and rubbed it on her tip. I moaned as she kissed me and slid her head in my hole. She started pounding me I moaned and she said you want your gfs cum in your ass today? I said yes.

She made out with me as I felt her cock explode in my ass. She pulled out I moaned I didn’t cum yet. I was informed by her I had to go to work and we could have fun before or after the nude beach that she would be picking me up at 12:30

I said ok I don’t have time to shower now, just then my phone buzzed for work. Feel free to wear sweats today as we are just rearranging offices for our move. I said oh we get to wear sweats. That’s way better, I was just pulling my panties off when my gf said wanna wear these and tossed me the ones she had on yesterday and slept in. I said stinky lol.

She said you know you wanna wear them for me. You can even borrow my sweat pants you like to wear. I laughed and said the ones that you like my ass in? She said yeah baby do it you are just moving boxes and desks. I said ok honey can you bring me beach clothes I need to get going so I can be done at 12:30. I was informed she would bring my clothes for pre beach since we would be going to nude beach.

Then I slid on my gfs cheeky black lace panties and the gray sweatpants. Not noticing you could 100% see panty lines, a panty outline, and the lace could be seen through them. I headed out the door. I got to the office and was paired with my 46 year old milf co worker. At the time I was 27.

She and I started chatting and she was recently divorced with 3 kids. She was complaining about the dating scene and that it’s hard in your 40s when you have 3 kids and are fat young guys with nice bodies like me have gfs. I laughed and said you look great. My coworker said yeah cause I wear body shaping clothes to hide my fat rolls and cellulite at work. I laughed and said not that bad cmon. She said yes I am 5’6” weigh 220 lbs have a 38” waist, and 58” hips, with size C smaller tits from all the breast feeding and a mommy tummy.

I laughed and said well I am sure guys think you are a milf. She laughed and said careful HR is gonna get made. In shock I was like ahhhh ahhhh. She laughed and said I am just kidding. Thanks but I am fat, I hate the beach too, either I gotta wear 1 piece moo moos and get tan lines or bikini and my fat rolls and cellulite ass hang out. I said you could go to Haulover It’s baked. She giggled and said my fat ass is not going there have you been?

I said going today with my gf. She said ooollala. I said yeah I m nervous. My coworker said don’t be your body is great and as long as you have an average or larger cock you should be fine (as she looked at my crotch). I said and what if I am huge? She giggled and said you are giving a cougar like me hot flashes. I laughed and said whatever I will let you know Monday how it is.

It was close to noon when my gf pulled up. We headed to the beach. My trans gf told me no need for a swimsuit because we needed to be naked if we were going to fun area.

I laughed, babe you forgot shorts for me. She giggled and said you have my panties I said I am a guy i can’t wear just panties and she told me I could.

We got to beach I stripped to just panties and we walked to nude area. I took panties off and she got naked. Her cock twice my size. I said I am cold and she giggled. People were staring at both of us as we found a spot drank beers and suntanned. It was a great day we hung drank and tanned. Strolled the beach’s few times but no one cared. My little cock got hard as we strolled by a few bbc men and black women and they pointed as my hard was still small than my gf. My gf said oh my you like bbc? At this point she didn’t know that I had been fucked by my roommates a lot and one was black.

I told her I am just horny you fucked me and I didn’t cum this am noting to do with them. She giggled and said ok and snacks my ass. I said well it ain’t gonna go down on its own lol. Then she took me to a secluded space and fucked me until we both came. She came in my ass and said mmmm now it’s gonna leak out on our walk and everyone will know you’re the bottom.

I laughed and said they already know that my cock is like 1/2 your size. She laughed and said true but maybe I like little cocks. I laughed and said you were hard when we walked by the bbc too. She looked and me and smiled saying duh, who doesn’t like big cocks in their ass. I said you miss it?

She smiled and spanked my ass, saying I miss huge cocks in my ass but love fucking yours. It’s a trade off I used to be the bottom. Now I am the top. I said I get that I used to fuck girls.

She looked at me and laughed oh babe we spoke about this gfs and pitty fucks. I said some girls aren’t size queens. She stroked my cock and said babe we are all size queens to some extent. I said do you want bbc in your booty? She smiled and giggles saying I still have dreams about it. I said oh well you want it?

She looks at me and says for real? I say what about a 4 sum? She says omg yes let’s do it. I know the guys! I say ok we can set it up in the next few weeks. She says yummy and deal. That night and Sunday we enjoy tons of sex together.

Monday I saw my coworker and she asked how beach was? I said amazing. She said that’s good then asked why I had panties on Saturday. I was shocked and said ahhh stayed at gfs had no underwear or pants clean borrowed sweatpants and panties sorry. My coworker chuckled no worries I thought maybe you liked cock and was thinking another one if the young hot ones that’s gay or has a tiny cock. I laughed and said I have a gf and she loves our sex life I giggled. My coworker said too bad for me and winked then said so Haulover was good? I said yes you should do it. She said maybe next Saturday.

Next week came and my trans gf said Haulover again. I said my coworker might be there. She said the milf one? I said yeah. My trans gf said babe who cares let’s go. I said what if she sees me? My gf told me not to worry we don’t need to talk to her if she is there. She asked what the big deal was. I said my coworker might see me with a boner. My gf said here wear one if these cock rings and you won’t get hard. There were 8 of them the first 5 were way too big. The 6th was getting close and number 7 and 8 were tiny. She said I got an idea baby and placed an ice pack on my cock and balls and my penis shrank to like 1 inch long and the ring was placed on. I said I am tiny. She said mmmmm yes baby but hot.

She handed me some panties and said wear these for me as we both back a beach bag. I said what else with panties and she said your white shorts he he I wanna see your panties. Then we headed out.

We got to the beach went to naked area and I took clothes off. Then we strolled the beach by the bbc. My gf again got hard but my little cock stayed limp. She said see we are good. I asked are we going to fuck again as I stroked her cock a few times. She said naughty boy you would have to take that ring off or cum soft. I said I just wanna feel you explode in my ass. She giggled and said mmmm babe deal.

We went in the secluded area this time 2 bbc were fucking a woman all I could see was her legs and ass. As one was in front getting a bj and the other behind doing her doggie. My trans gf said oh those were the days. I responded, what were the days and she said the getting tag teamed by two black guys with big cocks.

I said you want that instead of my ass? She giggled and said no baby maybe we do the group thing another time I want to cum in that sexy ass of yours. I got on all 4s and she fucked me doggie style. We could hear the other woman moaning as I moaned. Then my GF said baby I am gonna cum. I moaned already and she said you can suck me if you want a round two. I said ok babe full me then. She came in my ass and then laid on her back as I sucked her hard again. Then I climbed on top and rode her cock as she rubbed my tiny soft cock and balls. I dropped out some cum as she filled my ass again. I moaned so horny and she said tonight baby I promise you will be taken care of.

We got up to leave. I could feel cum leaking from my ass and she said so hot honey let it leak please no one knows us. I moaned ok as she slide a finger in my hole. As we were walking out we ran right into the two bbc and the woman. I double taked it was my coworker. She saw me at the same time and said hi and ummmm. At this point we had plants between us so could only see her upper half and the same for her.

My gf said who is this honey. I introduced my gf and coworker. Then we met no bushes. I saw my coworkers body amazing 40 ish year old chubby MILF body, dipole ass, stretch marks, mommy tummy and some chub in the right areas.

My coworker looked me up and down when she got to my cock she stared. Then she did the same to my gf and stared at her cock too. Then she said oh my not what I expected running into you.

My gf said oh he didn’t tell you that you had a cock? My co worker said no and he let off that he had a big cock. My gf said oh what else did he say? Coworker stated that he had a hot gf and you fucked all the time. That he was hung, sex with a big cock is amazing, he wore panties cause he forgot clothes, he was a ladies man before you etc.

My gf well got upset and said are you embarrassed of my big girl cock? I said no honey I love it that’s why I said sex with a big cock is amazing.

Gf well as you can see small cock for him big for me. We do fuck a lot his ass get lots of cum in it. He tells me he was a lady man before and lol I don’t believe it, he wore my panties cause I told him too but he had his own.

My coworker giggling the whole time. Then asked did you just fuck him? My gf said yeah he has my cum leaking out, co worker says oh my lol I don’t feel so bad with my creampies leaking now. My gf said well know at work most days my cum is in his ass and he has panties on. My coworker giggled and said good to know.

I said whatever let’s go chill and drink. I walked ahead and my coworker said nice cum leaking from your ass. My gf and her were chatting and giggling. My gf said we are stopping by bbc babe you are really leaking from two loads put panties on if you plan to sit on towel. I got black and grabbed panties and put on as I sat down and drank a beer.

A few mins later my gf came back and said it’s your lucky day. I said really how my coworker just saw me. My gf said she is quitting soon and gonna keep today a secret as long as we all do a massive GB tonight with some of the bbc and her.