Daddy's Friends

Daddy called me and said he wanted to introduce me to a few of his friends, so wear something cute. Daddy had been telling me for days that he wanted to show off his little sissy boi to his friends. Put on my floral sun dress and the pink Nike’s that I love, I headed over to his place to be shown as gurl candy. When I arrived, daddy pulled me into the middle of the living room as his old friends looked at me with dirty smiles and made several comments about me as if I was not even there. Daddy said his friends “may” want to play with me for a while. He ordered me to remove my skimpy panties… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 1

My Best Friend's Uncle

My friend Matt was having a going away party. We had been best friends for years and he was one of the first people I talked to before really embracing my lifestyle. He was always so cool and defended me when bullies in school would tease me. I even offered to blow him once in college, but he said that just would be too weird and he is strictly for girls, but we stayed the best of friends. Many of the people at the party knew my lifestyle and some of my old friends actively made passes at me from time to time. Matt told me to just be myself because I knew most of the people there, so I had a… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 2

Mean Old Man

Another "friend" had set me up with an older guy. Before the meetup, I shaved everywhere, and rubbed down with coco butter (the smile is fantastic). Next, I knew I had to put on striped short blue body dress that really highlighted my best asset…my ass. Finally, my white pumps and of course my favorite cherry lip gloss. Just in time the apartment buzzer went off and there was my date, Angelo. He was in his late 60s around 300 lbs, unkept and just looked like a huge white slob. I was not impressed. It was surprising that he seemed a bit unwashed, like he just was at a job site and strolled ov… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 1

His Cock Was Almost Too Big

I met a new guy that I really connected with, and we were meeting almost every day to just hang out. For the first week or so, we did a lot of heavy making out, but we both knew it was time to take it to the next level. So, the next time he came over, I was in a super sexy tight mini, black thigh highs with lace at the top. For an added touch, I wore my pink heart locket tied together with a light pink ribbon. I walked out of the bedroom after getting prepared for Mike who was patiently waiting on the couch, he was all smiles. After another heavy make-out session I helped him remove his pants… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 1

Fucked By A Friend Of A Friend

A friend of a friend who knew I loved older men said he had someone he wanted me to meet that was in town overnight. After exchanging a few raunchy texts, I sent him my address and told him to bring condoms…just in case. He said he would be at my place in 20 minutes. That gave me just enough time to get dolled up. Putting on a tight little red mini dress that barely fell below my ass, black thigh highs, heels, my favorite black wig with red highlights, eyeliner, and glossy peach lipstick I was ready to greet him. Hearing a knock on my door I turned the lights down and my heart started racing a… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 3

Immigrant’s Sissy

“Okay you fucking cow, get on your back and spread your legs wide” In my tight little sexy bunny outfit, I lie on the bed, rock back and spread my legs wide as I can. “I have been looking forward all day to watching you try to cock in your faggot ass.” “Trust me when I’m done its with your fat ass, its going to be my pussy” he said in a heavy Slavic accent. He smiled as he slapped his girthy old tool across my sissy nuggets and little clittly. “I thought all you guys are supposed to have huge dicks that the white women can’t wait to have in their pussies” Now he started to laugh, the more he l… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 1

How it feels when a guy cums in me

I was asked “How does it feel when a guys cums in you?” by a friend. I let him know it’s different for everyone. For me it’s all the actions together because sometimes you cannot “feel” when the guys cums. I love everything from the heavy breathing when he is about to shoot his load, to when he pulls out afterwards. This is how I explained my experience…. As his rhythm quickens, sometimes I feel his cock start to swell even more before. I know what is about to happen and it is almost mind numbing. He is deep in the act of fucking me, so it’s the force of having a cock in your ass pumping back… Daha fazlasını okun

İletiyi yazan MatureBrownMan 1 yıl önce 2

The Guy I Blew

I finally decided to take my crossdressing to the next level. I have been dressing for a while now at home, playing with my toys and I felt like it was time to make a move. I made a Squirt ad about meeting a guy for drinks and fun then posted it. After filtering through the responses, I found the man I would service for the first time. He read my response back to him, and said he wanted to meet ASAP. I left the computer to go get myself ready. I did my makeup with blushed cheeks, dark brown eye shadow, pink lips with lip gloss and my nails in a bright girly pink. I love rubbing baby oil on my… Daha fazlasını okun

İletiyi yazan MatureBrownMan 2 yıl önce 2

Never Tease a Stranger

At a bar’s costume party, you notice me in my plaid mini, pink t-shirt, my hair in a pony-tail, pink ball cap, white ankle socks and pink sneakers. You start sending me free drinks and shots. After working your way over to me we talk some. Its crowded and you move is to stand behind me almost pinning me against the bar to order drinks. After the third time I ask, “Are you done dry humping my ass?” we laugh. After a few more shots the bartender tells me to slow down, but you say you have plenty more at your place. I feel I’m in control and since around 2am I agree to a few more drinks at your… Daha fazlasını okun

İletiyi yazan MatureBrownMan 2 yıl önce 1

Bullied By Building Landlord

My most recent fantasies are about being bullied.... I still have a thing for older white men, this is about Carl the building manager. He is about 6'2, very stocky, in his early 60’s. He came to “discuss” my overdue rent. I told him I would be home at 10pm. Wanting to get on his good side, I had my long black curly wig, high gloss strawberry lip stick, pink skirt that snuggly covered my big butt and pink reeboks. I tried to look extremely cute because he was always looking me over. He’s gruff and a bit creepy, but I loved my little apartment and didn’t want to lose it. Right on schedule… Daha fazlasını okun

İletiyi yazan MatureBrownMan 2 yıl önce 3

Last Night's Sissy Dream

The knock had barely started before I opened the door, I was about to invite him in, but before I could, he had already let himself in. He looked so different than his profile pictures. This guy was tattooed from his neck down with a tear-drop tattoo at the corner of his eye. With a nasty, dirty freezing stare he quickly he looked me up and down and closed the door. I gave him a nervous smile, but he focused on my short dress and my legs. Already, I wondered if this was a mistake. Stuttering, I questioned him about his profile picture, and he said it was old and continue to walk right in makin… Daha fazlasını okun

İletiyi yazan MatureBrownMan 3 yıl önce 1

Daddy Brent

One Friday after a long week of work, I headed home, then after a few glasses of wine jumped in the shower. After completely shaving, I was so soft and smooth. Toweling off, applied lotion and picked out my favorite outfit. Putting on panties and stockings from the “Pink” store, it was time for my super short mini skirt. I snapped about 10 photos selfies and uploaded them to Fetlife. I ended up getting about 20-25 responses! After back-and-forth chatting, I finally settled on one daddy. He was a bit husky and very hairy with a super thick 7” cock. My little dickey got fully erect without touch… Daha fazlasını okun

İletiyi yazan MatureBrownMan 3 yıl önce 1

My Neighbor Frank

Living by myself allowed me to experiment with waxing my legs and shaving my body hair. I bought my first butt plug and white dildo by mail; I was too ashamed to get them from the Adult bookstore a few blocks from my home. I even bought my new set of underwear through the mail that made my oversized phat caramel ass stand out. My living room window face out towards another 3-story apartment building and I would frequently walk around in girly heaven, dressed only in panties and an oversized top. I knew my neighbor Frank across the across the building could see me and that was fine. Frank was… Daha fazlasını okun

İletiyi yazan MatureBrownMan 4 yıl önce 1

A Sissy’s New Daddy Search

I couldn't sleep last night so I figured I'd fire up the laptop. Lately I have fantasized about being totally dominated and used by a real top daddy since my old one moved away. When I’m in this type of mood I usually will do a quick hookup, but I was in such a sassy state, I really missed having a man taking charge of me, to humiliate me. It was a good night, I was getting a lot of messages from guys interested in teaching a little sissy how to keep her daddy happy, and how my fat brown ass needs dick. Most were BBC. One guy though...his cock was magnificent. 8in long, cut, and almost coke… Daha fazlasını okun

İletiyi yazan MatureBrownMan 4 yıl önce 4

A Sissy’s New Daddy Search

I couldn't sleep last night so I figured I'd fire up the laptop. Lately I have fantasized about being totally dominated and used by a real top daddy since my old one moved away. When I’m in this type of mood I usually will do a quick hookup, but I was in such a sassy state, I really missed having a man taking charge of me, to humiliate me. It was a good night, I was getting a lot of messages from guys interested in teaching a little sissy how to keep her daddy happy, and how my fat brown ass needs dick. Most were BBC. One guy though...his cock was magnificent. 8in long, cut, and almost coke… Daha fazlasını okun

İletiyi yazan MatureBrownMan 4 yıl önce

I Was Asked About My Quickest Hookup Ever…

Quickest ever was about a few years back, when I visited a bar round 2 in the afternoon. I wasn’t really dressed up; just in leggings, makeup and earrings. The bar showed gay and transgender videos on the monitors instead of sports which was a nice change of pace. Some guy talked me up as soon as I sat down and kept buying me drinks. We had some small talk about him being in town to meet a client and blah, blah blah. A few times he caught looking at has swelling bulge as we talked and drank. He asked to play a game of darts after adjusting himself a few and I was like “sure.” Thank God no o… Daha fazlasını okun

İletiyi yazan MatureBrownMan 5 yıl önce 1

Sissy Thoughts...

I think of you sitting on the couch with your big dick at full attention and you patting your lap commanding your little gurl to sit on it. As I slowly walk over you tell me to remove my cotton panties from under my dress. I first kneel in front of you because I need to taste that chocolate meat first and I am so happy that you nod your head giving me approval to suck you first. Taking the head of your dick in my mouth, you grin as I first roll my tongue over your pee slit. I begin going up and down the length of your nice tool as I hear you say, “Good girl.” I next feel one of your hands on… Daha fazlasını okun

İletiyi yazan MatureBrownMan 5 yıl önce

Brute At The Video Booth

I was back in El Paso on business for a few days, I and remembered having a really fun time at a very seedy off the road adult booth and sex shop. The place was always full of mostly Latino dick of every age, size and type. The first time I was there, I was in heaven sucking every type cock being fed to me; cut, uncut, large, small, beefy, you name the cock and I sucked it! This time I decided to totally fem out and give the guys a look at a little cock-teasing whore. Cute wig, earrings, painted nails, purple top, short-short skirt and white laced stockings with matching heels. I arrived late… Daha fazlasını okun

İletiyi yazan MatureBrownMan 5 yıl önce 2

Daddy’s Faggot, Round 2

After our first session, I am still in the doggy position and breathing hard from the anal workout you put on me. I am so relieved that you finally came because my poor sissy pussy feels wrecked. You get up and move to the over side of the bed. My sweaty body sags over the pillows, but you still have a raging hard-on to my disbelief. “Get on your back whore!” I must have moved too slow because your powerful arms forcefully push me on my back. Grabbing me by my fleshy ankles and right under my high-heels you drag me to the edge of the bed, then you fold me over, firmly pushing my legs back, so… Daha fazlasını okun

İletiyi yazan MatureBrownMan 6 yıl önce

Grandpa Fantasy

Lately I have been this fantasy lately….. I have agreed to be the target of a secret bukkake party by several older horny men ranging for 60 to over 80 years old. I ring the doorbell and I’m greeted by the first senior citizen and see several others lounging around in different stages of being dressed. I am welcomed into the house and immediately escorted to the bedroom as my ass is groped and fondled under my mini skirt by greedy hands. A line of horny guys begins to follow where I am being led, some guys already have their cocks in the hand, jacking them hard. The whole time I am being le… Daha fazlasını okun

İletiyi yazan MatureBrownMan 6 yıl önce 4