Stefanie's Crossdressing Memoirs Vol. 5
Despite my little misadventure the very first time I went out as Stefanie, I was not deterred in any way from dressing up for other men's enjoyment. In fact, I think it honed my craigslist slut senses quite a bit. I was becoming more adept at filtering through all the bs when I would post an ad on craigslist. And the trend that I observed was that older men in their 40s and 50s were much more comfortable getting sucked off by and fucking a crossdresser than were guys my age in their mid-20s. So it was time for me to give a rebound blowjob after my little run in at the lake park.
In my last post I mentioned that in addition to being a regular on craigslist, I was also on several dating sites--one of those primarily catering to men who were seeking other regular men. Crossdressers on that site were a pretty niche community--there were plenty of guys with pics of them in at most panties or pantyhose but certainly not fulling dressing men who were trying to be at least semi passable. Of course there's nothing wrong with that, and if you've read my other posts you probably know I personally don't aim to be 100% passable, I like being a man in makeup, a wig, and a tight sexy outfit with some high heels.
But enough preamble, so I started talking to a guy on the aforementioned dating site and all the indicators that he was for real were there. He was an older top, with a big stocky body which I thoroughly enjoyed. Being close to 6' tall before heels and a pretty athletic 200 lbs., one thing I really enjoy is having a man who is bigger than me. That always made me feel like a real sissy to have someone bigger than me whip it out so I could get down like a good gurl and service them like a crossdresser should.
My new friend was dominant in our few emails exchanged, but not rude. After so many emails and texts and whatnot, there is a pretty clear difference to me. Men being dominant is a major turn on for me, but rudeness is more about not sending any pics and demanding I meet, sending a one sentence email and expecting me to have you over immediately or jump in my car and drive to you, getting belligerent when I don't answer an email fast enough.
The reason I mention his dominant nature is the premise for our first meetup. It was a weekday morning, and I had the day off from work. I hadn't gotten dressed up, but I was logged on the dating site and my friend sent me a message since he was on the mobile version of the site. He said he had some free time in the afternoon and wanted some head and to fuck some sissy ass. I had some things to do in the afternoon, but he said that he knew I wanted his cock so I should be a good little gurl and wear something sexy for him when he got to my place. He was absolutely right that I couldn't deny Stefanie that opportunity to get dicked down so I adjusted my plans for the day and in the early afternoon I started getting ready.
I showered and got nice and smooth, put on some lingerie with some stockings and heels, then finally stood in front of the mirror and did my makeup. I always reveled in doing my makeup before a meet, I loved looking at myself in the mirror with my wig cap on but no wig as I applied lots of makeup which I knew my guys enjoyed. And I especially loved being able to see the difference in the mirror after sucking cock or getting fucked good. I added a new little touch to my outfit and wore some long black opera gloves, I had a feeling my friend would appreciate how they would feel on his cock when I would have it in either hand. I made final adjustments to my wig and checked my messages to see if my man was on his way.
He pulled up in front of my of house on his motorcycle and made his way to the door. Although he was shorter than me, I still enjoyed that he had a thick body that helped me feel like a little sissy bitch. He looked at me and said that he knew I'd dress up sexy just for him because I was his little crossdressing cocksucker. That really turned me on so I took his hand and walked him to my bedroom, making sure to wiggle my butt extra for him as he followed behind me.
I sat him down on the bed and kneeled down in between his legs. I undid his pants and pulled them to his ankles, then I saw his nice thick 7" cock. He was already getting hard before I even had a chance to wrap my lips around it. He laid back as I went to work slurping all over his cock getting it nice and wet. I climbed up onto the bed and kept sucking his cock while I turned my ass toward him. He rubbed my lace panties and pressed them against my tight hole which made me moan while I had more than half of his cock in my mouth. He started calling me names and telling me what a good little cocksucker I was for him, which I loved and I knew he could tell I was getting off on being degraded like that.
He started fingering me when I got back off the bed and kneeled down in front of him once more. I grabbed my dildo which I had placed nearby beforehand and starting lubing it up. I knew I'd need to warm myself up for him to fuck me. I rode up and down on my dildo in time with my head moving up and down on his cock. He pulled his cock out of my mouth and said that if I wanted to dress up like a girl for him, then he was going to make me his girl. I knew exactly what he meant so I slid a condom on him and lubed him up, then I got up and bent over my bed with my ass in the air. The entire time I got him ready to fuck me he continued calling me all manners of sissy, bitch, faggot, cocksucker, queer, etc. and I played right into and wanted nothing but to please him and earn his approval and nice big load he had waiting for me.
Loosening up with my dildo payed off because he was able to slide his cock right into me and pound away. He pushed my legs up against the bed and pushed my upper body down on the mattress while he fucked me. He grabbed my head at one point and that messed up my wig. When that happened he said "yeah that's right you're just a sissy boy who likes dressing up like a slut for daddy aren't you?" In between my moans I could barely whimper out "uh huh oh yeah daddy fuck me hard." Of course for me it didn't seem like long enough, but I could feel him start to tense up so I knew he was getting ready to cum. I decided to just let him cum how he wanted so I soon felt his last few extra strong thrusts as he groaned and slowed down pumping my ass, coming to a stop. He pulled out so I got to work cleaning him up, managing to get a little bit of his cum on my fingers to lick up. He got dressed and said he had to get back to work, so I walked him to the door and thanked him for a good time. He said see you next time naughty girl and walked to his motorcycle and rode off.
I went back to my room and flopped on the bed for a few minutes to catch my breath when I realized that I didn't cum during our entire meetup but it didn't bother me one bit because I was too busy enjoying the pounding he gave me. I put my dildo back in, which went in effortlessly, and then gave myself a self-facial. That accentuated my messed up makeup quite nicely when I went to the bathroom to clean up.
Now that my rebound fucking was complete, Stefanie was once again ready for a night on the town, which I'll be discussing in my next post. Hope to see you there!
Muah!
xoxo
-Stefanie
In my last post I mentioned that in addition to being a regular on craigslist, I was also on several dating sites--one of those primarily catering to men who were seeking other regular men. Crossdressers on that site were a pretty niche community--there were plenty of guys with pics of them in at most panties or pantyhose but certainly not fulling dressing men who were trying to be at least semi passable. Of course there's nothing wrong with that, and if you've read my other posts you probably know I personally don't aim to be 100% passable, I like being a man in makeup, a wig, and a tight sexy outfit with some high heels.
But enough preamble, so I started talking to a guy on the aforementioned dating site and all the indicators that he was for real were there. He was an older top, with a big stocky body which I thoroughly enjoyed. Being close to 6' tall before heels and a pretty athletic 200 lbs., one thing I really enjoy is having a man who is bigger than me. That always made me feel like a real sissy to have someone bigger than me whip it out so I could get down like a good gurl and service them like a crossdresser should.
My new friend was dominant in our few emails exchanged, but not rude. After so many emails and texts and whatnot, there is a pretty clear difference to me. Men being dominant is a major turn on for me, but rudeness is more about not sending any pics and demanding I meet, sending a one sentence email and expecting me to have you over immediately or jump in my car and drive to you, getting belligerent when I don't answer an email fast enough.
The reason I mention his dominant nature is the premise for our first meetup. It was a weekday morning, and I had the day off from work. I hadn't gotten dressed up, but I was logged on the dating site and my friend sent me a message since he was on the mobile version of the site. He said he had some free time in the afternoon and wanted some head and to fuck some sissy ass. I had some things to do in the afternoon, but he said that he knew I wanted his cock so I should be a good little gurl and wear something sexy for him when he got to my place. He was absolutely right that I couldn't deny Stefanie that opportunity to get dicked down so I adjusted my plans for the day and in the early afternoon I started getting ready.
I showered and got nice and smooth, put on some lingerie with some stockings and heels, then finally stood in front of the mirror and did my makeup. I always reveled in doing my makeup before a meet, I loved looking at myself in the mirror with my wig cap on but no wig as I applied lots of makeup which I knew my guys enjoyed. And I especially loved being able to see the difference in the mirror after sucking cock or getting fucked good. I added a new little touch to my outfit and wore some long black opera gloves, I had a feeling my friend would appreciate how they would feel on his cock when I would have it in either hand. I made final adjustments to my wig and checked my messages to see if my man was on his way.
He pulled up in front of my of house on his motorcycle and made his way to the door. Although he was shorter than me, I still enjoyed that he had a thick body that helped me feel like a little sissy bitch. He looked at me and said that he knew I'd dress up sexy just for him because I was his little crossdressing cocksucker. That really turned me on so I took his hand and walked him to my bedroom, making sure to wiggle my butt extra for him as he followed behind me.
I sat him down on the bed and kneeled down in between his legs. I undid his pants and pulled them to his ankles, then I saw his nice thick 7" cock. He was already getting hard before I even had a chance to wrap my lips around it. He laid back as I went to work slurping all over his cock getting it nice and wet. I climbed up onto the bed and kept sucking his cock while I turned my ass toward him. He rubbed my lace panties and pressed them against my tight hole which made me moan while I had more than half of his cock in my mouth. He started calling me names and telling me what a good little cocksucker I was for him, which I loved and I knew he could tell I was getting off on being degraded like that.
He started fingering me when I got back off the bed and kneeled down in front of him once more. I grabbed my dildo which I had placed nearby beforehand and starting lubing it up. I knew I'd need to warm myself up for him to fuck me. I rode up and down on my dildo in time with my head moving up and down on his cock. He pulled his cock out of my mouth and said that if I wanted to dress up like a girl for him, then he was going to make me his girl. I knew exactly what he meant so I slid a condom on him and lubed him up, then I got up and bent over my bed with my ass in the air. The entire time I got him ready to fuck me he continued calling me all manners of sissy, bitch, faggot, cocksucker, queer, etc. and I played right into and wanted nothing but to please him and earn his approval and nice big load he had waiting for me.
Loosening up with my dildo payed off because he was able to slide his cock right into me and pound away. He pushed my legs up against the bed and pushed my upper body down on the mattress while he fucked me. He grabbed my head at one point and that messed up my wig. When that happened he said "yeah that's right you're just a sissy boy who likes dressing up like a slut for daddy aren't you?" In between my moans I could barely whimper out "uh huh oh yeah daddy fuck me hard." Of course for me it didn't seem like long enough, but I could feel him start to tense up so I knew he was getting ready to cum. I decided to just let him cum how he wanted so I soon felt his last few extra strong thrusts as he groaned and slowed down pumping my ass, coming to a stop. He pulled out so I got to work cleaning him up, managing to get a little bit of his cum on my fingers to lick up. He got dressed and said he had to get back to work, so I walked him to the door and thanked him for a good time. He said see you next time naughty girl and walked to his motorcycle and rode off.
I went back to my room and flopped on the bed for a few minutes to catch my breath when I realized that I didn't cum during our entire meetup but it didn't bother me one bit because I was too busy enjoying the pounding he gave me. I put my dildo back in, which went in effortlessly, and then gave myself a self-facial. That accentuated my messed up makeup quite nicely when I went to the bathroom to clean up.
Now that my rebound fucking was complete, Stefanie was once again ready for a night on the town, which I'll be discussing in my next post. Hope to see you there!
Muah!
xoxo
-Stefanie
6 years ago
