Another sexual adventure of mine a few years later...
I would be 22-23 now, working a decent paying part time job and living in my first appartment. The internet just starting to hit it's stride in porn and good online gaming starting to emerge. For a couple years all I did was smoke dope, play Quake2 and surf for porn.
Came across an online profile of a dominant TV here where I live. We emailed back and forth a few times, sharing pics and thoughts. She sent me pics of her dungeon and it looked impressive! There was a bondage chair, cross, bench & stocks along with all the accessories.
She agreed to see me after some time online and talking on the phone. On a cold friday night I went to her place at 9PM as instructed. Walking up to the house, I knocked and opened the back door, then stepped inside as she told me to do on the phone earlier. Standing there I could see her long red hair directly down the staircase in front of me. She said to take off my shoes and come down. When I got to the bottom of the stairs all I saw was WOW! She was tall and slender with a PVC teddy, 45-50 years old, thigh high platform boots, and the longest bright red nails I've ever seen. Big red hair and make up but not passable, but very hot none the less.
The basement was nicely set up and clean. Walking into a living/family room from the stairs,I sat on the sofa and we chatted a bit. We talked about limits and desires and of coarse a safe word.
She stood up then told me to strip and lay my clothes on the sofa. As I was taking off them off she walked out of the room. Standing there naked and shaking a bit from nerves, she walked up, pushed me to my knees and puts on my collar. Attatching the leash, she said to follow her like a good boy on my knees. I was then led to a medium sized room that was her dungeon. She sat on a high stool with me in front of her on my knees. She took my chin with her hand and raised it, making me look into her eyes.
"You're a pig!" she yelled.
Have to admit I was a bit shocked. Next thing I knew she slaps my face and says "Pardon me?"
Ok now I AM in shock. Very scary and confusing for me now.
Slap. Another of her hand on my face. "You will respond with a 'Yes Mistress' or a 'No Mistress' when you are talked to. Do you understand?"
"Yes"
....Slap... "Pardon?"
"....Yes Mistress"
Looking back on this, this was an amazing experience! This is where I would allow myself to totally submit. 'Yes Mistress' - two words that says you've given up control.
After a bit more verbal training with the aid of her riding crop she put me up on a bench with stocks. With me on my knees on this flat bench and my head and hands locked up in the stock and unable to see behind me she would proceed to flog me.
Have to admit the first time you see a flogger it does look very intimidating. Long thick handle with lots of leather strands. The bark is a bit bigger than the bite. It didn't hurt so to speak but you still felt it. And it felt kinda good.
All I could see in front of me was a framed 8X10 photo of a very large erect cock. Off to the sides I saw more equipment and such. Looking at this photo, hearing the sounds of her moving around, her voice, her breath. The the feel the sting of her hand smacking my ass and feeling the soft thud of her flogger as well. After a bit I figured it out.
The clicking of her high heeled boots would stop. She was lining me up for a smack. That was her patern. Move and strike. Talking down to me the whole time. Even after I figured out when I was going to get my ass struck, it was still a suprise! LOL I loved it.
After my session, we chatted a bit and I gave her a ride to one of the gay bars in town. She asked me to join her and said it's a lot of fun but I couldn't. Had to get to a friends place and I couldn't stay.
Never saw her again. For a while after that I was too scared to try again. That was too bad, looking back that was probably the favorite sexual experience of my life.
My first gay experience happend when I was 19. I lived out of town and drove into the nearest city. I sat in my car and called a male chat line. Listening to profiles of men describing their cocks and what they were looking for was so hot. I came across a guy who said he loved to suck taxi drivers, truck drivers and young guys. We chatted for a bit and made plans to meet him at his place. When I got there I was soooo nervous and he could tell. We sat down in his living room where he had some bi porn playing on the T.V. I sat there shaking watching a MMF three way. Looking down on the floor, he had a bead spread laid out. I could see condoms, paper towel, baby wipes, and lube. I also saw a small brown bottle of poppers. Didn't know what poppers were until years later.
After a few minutes of watching the porno he moved over and started petting my cock and balls thru my pants. When he realized that I was hard he undid the button and fly of my pants, pulled them and my undies down a few inches, reached in and pulled my cock out.
There I sat in front of this stranger with my cock exposed.
He stood up and took off his pants and shirt. There he stood naked in front of me and asked if I would like to lay down to get blown. Nervously, I stood up and stripped. He gently rubbed my body as I took my clothes off. Laying down in the front of the T.V. he started to suck and lick. Oh God, what the fuck is happening!?!?
It was so hot. I couldn't control myself. I came right away.
I was so embarassed and disappointed. I wanted it to be better. I wanted it to last forever.
He just laughed, said "that's ok. I remember my first time too".
"Would you like to stay longer"? he asked. I quickly said yes.
I got hard again right away and he started sucking again. So good. It felt sooo fucking good. I reached over and fondled his cock and balls, first time touching another man was scary but I couldn't stop. Next thing I knew we were 69ing with me on top. The head of his cock in my mouth, him sucking even harder now. Knowing he was getting excited made me even hotter.
There in the light of the television playing porn, in some strangers appartment at 2AM, I sucked my first cock.
He asked if he could rim me but that kinda freaked me out and I declined. If only I knew how good poppers and being rimmed felt! Sadly it would be years before I experienced that.
After a while I was ready to pop again. He swallowed it all and I got off of him. He got onto his knees and asked if he could jerk off while admiring my ass. I turned around, bent over and watched thru my legs as he jerked off staring at my ass. After he came all over himself, I got dressed, thanked him and left.
I am thankful my first was as good as it was. He was a nice guy.
Many years later I came across an online profile that sounded like him. I hit him up with an email and we still see each other now and then to this day.
I've been dressing off and on for years and everybody has their first CD/sissy experience, here's mine.
The very first memory I have of my sissy inclination was as a kid. I was maybe 12 or 13 and I would sneak the Sears cattalog to a nice private location and masterbate to the women's intimate section. I loved how sexy women looked in lingerie. One day I snitched a pair of my mom's matching red bra and panties so I could feel for myself what lace felt like against my skin. Well, I guess I really never looked back huh?
I never returned the underwear, I hid them and would put them on when ever I could sneak away to jerk off to those sexy Sears models. Can't remember what happened to them. I really loved mom's underwear.
A bit about what I like and think of from time to time.
I've been thinking of going to an ABS and get into some glory hole fun. I've been a couple times in boy mode and it although it doesn't appeal to me like that, the thought of being there dressed is exciting. Mmmmm sucking some anon cock while dressed. Makes me wet! Pics of me sucking anon cock at the glory hole - now I'm dripping wet! LOL
The bathhouse is another interesting place I'd like to visit dressed. There's one here in town that has 'Fetish Night' once a week. They say leather, lace, etc. Could be fun. Been too chicken to try it tho.
I've always loved older women. Only dated one that was younger - what a waste of time that was. Older women rule.
I've loved trannys from the first time a saw a pic of one on a box cover at the adult video store. Loved looking at them ever since.
I've sucked, been sucked, had my ass eaten and gotten fucked both dressed and in boy mode. Always prefered it dressed. Sissy to the core.
I like older men. I like daddies. I like older bears.
I love cross dressers. I love transvestites. I love transexuals.
I love dressing like a girl. I love dressing like a woman. I love dressing like a slut. I love dressing like a whore. I love to dress up perriod.
I Love cut cock. Semi cut is cool too! Lots of foreskin not so much. Sorry, just my thing.
I've been dominated by a transvestite once. Me in a stock. Getting flogged. Why I haven't done it since baffles me too. It was so exciting.
I've had one on one encounters with CD/TV's and older men. I've never been in a threesome. That's a shame.
I love poppers. I love the way it makes me feel like a slut. I crave cock when I sniff. I love the feeling of a cock in my mouth high on poppers. I love getting eaten out while sniffing poppers. Getting fucked while sinffing poppers is the only way to truly be able to take it like a girl. Poppers make me feel like a whore. Poppers are my sissy side's best friend.
Well, the flu is gone and I'm back up to normal again, YAY!
I've stumbled across single pics of me here and there. Thanks to those for adding me to your galleries! I appreciate that there's a few that like my pics enough to add them to their CD/TV galleries. It's very fattering. I am still looking for a personal biographer to caption some exclusive content. If interested, send me a message. Interested parties should have caption experience and galleries of their work on their profile.
I'm looking to do some clothes shopping but can't decide what to buy. Hmmm, leather, lace, or ??? There's so many nice clothes that sissies can wear. Any comments or suggestions of what my fans would like to see are always welcome. I am still looking for a good outdoor location to take some dirty pics as well. Please be patient - hoping to get this done in the next week - so please stay tuned!
It's just so damn exciting seeing myself captioned! It really is a huge rush, so thanks to all who have shared their dirty thoughts to my pics. It would be really hot if I could find a personal biographer to caption some exclusive content and post it.
I have been down and out with the flu and just starting to get better. Hope to go out and get some outdoor pics when I'm 100% again...stay tuned. LOL
Great job. Thank you soooo much for making my day!
Hope you all had a safe and fun filled New Year's Eve. I happened to be working so it was quiet for me. I did find some time to grab a few new pics for you this last week - check out my galleries for the latest from Lola's web whore studio!
Been trying to put together a new sissy trainer vid but having problems with Windows movie maker hanging up. Any suggestions of a good movie maker that others on here are using would be appreciated!
Anyways, thanks to all who are fans. I really get off showing for you and hope you like my new additions. Always looking for outfit requests for those looking to caption. Till next time pervs and pervettes
Well, uploaded a couple sissy vids. The first one not so good, the second attempt a bit better. Will try and do another and expand it a bit.
Put up some new pix. Took them on Boxing Day, hope you like and caption them. I am getting bored of my limited photo set areas and am looking to get some new pics in some different locations and places. Maybe have a stunt cock or other sissy with me to help? LOL
Stay tuned and thanks to all who like my pics and are fans!
Saying hi to all the other pervs out there! Cross dresser looking for friends and model buddies. Love the fetish and sissy looks and posing for the camera is my favorite! Always on the hunt for a new sluty look. I am interested in meeting other dressers for fun and photos.
