By the time I turned eighteen I had built a big collection of women’s clothes and accessories to dress up in. I’d spent years cross dressing privately, getting off to the fantasy of a man taking my anal virginity. I eventually thought about looking up guys on the internet to hook up with, and found one man who was perfect for what I was looking for. He was a single older man named Tom who lived out on a ranch where he had lots of privacy. After we made arrangements, I immediately started getting ready. I showered and shaved my body clean, then painted all my nails hot pink. You’d be surprised how much men love pretty toenails during a footjob. I then did my makeup very thoroughly, to look the most passable. I topped it off with a medium length brunette wig.
I picked out a very specific outfit for this guy and where I was going. Since I was heading out to a ranch, I decided to dress the part and go for the farmer’s daughter look. First, I slipped on a black lace thong with a matching bra. Then I put on a brand new pair of black Anne Klein tights, since I love a man who admires my legs. I wore a black button blouse with a grey jean mini skirt, and black cowgirl boots. I took a look in the mirror, grabbed my purse and was on my way.
I was pretty passable, but I still wanted to drive at night to lessen my chances of anyone seeing me. As I drove there my mind was racing. This was going to be my first time getting fully dressed up for a man, let alone having sex with him. How would this go? Should I go through with it? By the time I had my final thoughts against it, I had already arrived. As I checked my makeup one more time in the mirror, a tall handsome man walked out of the front door, and waved at my car. He greeted me with a, “Hey, Mischa?”
“Hey there… Tom?” I replied.
“Yeah, I’m glad you made it! Come on in, and grab you a drink,” he said, smiling.
As I stepped out of the car, I could feel his eyes scanning my body, then he took my hand like a gentleman. “You look absolutely gorgeous, I can’t believe I get you all to myself,” he commented with an elevating whistle.
I was very flattered, but still anxious at the same time. He’d basically indicated that he was going to have his way with me by the end of the night, but it got me excited. I responded with a very girly, “Why thank you darlin’,” and wrapped my arm around his as he walked me to the entrance of the house.
When I walked in there was a fire going and laid out on the table were two wine glasses, a bottle of lube, and a couple of towels. I knew I was at the point of no return, so I embraced the situation. Tom poured us some red wine and turned on some music to set the mood. As the wine and flirty conversation loosened us up, he began to caress my legs. Feeling his hands run all over my tights sent jolts through my body and I could tell that he was loving it just the same.
“I absolutely love your black tights, Mischa. How about a foot massage?” He then slipped my boots off one by one and began fondling my feet. You could see my hot pink toenails through my tights and he began kissing them. “Oh baby… You have very sexy feet. They’re making Daddy really horny.”
I didn’t even notice that he had unbuttoned his pants and had his big stiff cock out.
With him still sitting on the couch, I switched positions and stared closely at his big dick. Before I could even think, Tom’s hand was on the back of my head and his fat cock was already in the back of my throat. I sucked his shaft to the balls, with saliva dripping down my face. I ran my lips up and down while my tongue did a swirly motion on his tip. Tom was face fucking me so well pre cum started dripping out my my hard little cock and into my panties. Tom’s dominance took off when he spanked my ass with his cock in my mouth and made me suck his two index fingers. I braced myself, knowing what was coming next.
He pulled up my skirt, put his hands down my tights under my panties and shoved his fingers into my tight ass. I let out a loud girlish moan and paused while his hard cock marinated in my mouth.
“Ohhh Mischa, you’re so tight! I can’t wait to shove my cock into you.” He grabbed the bottle of lube and began lubing up my virgin asshole as I continued to suck his dick like a hungry little girl.
Tom then picked up my chin, wiped my mouth and said, “Why don’t you go grab Daddy a condom over there?”
As I popped up off my knees on the couch, he slapped my ass covered in tights. I unwrapped a condom and slowly slid in onto Tom’s monstrous cock. The girth alone had me worried, but again, I was at the point of no return. Tom took my skirt off, picked me up and set me down to straddle him face to face. He grabbed my face and shoved his tongue into my mouth. My little cock began to tingle. He groped my ass and feet while we kissed.
I whispered in his ear, “I want that cock, Daddy. I want you to fuck me good.”
We were both drunk with lust at this point. He shoved his hands down my tights and started fingering my ass again, but just as our wet tongues wrestled, I felt his grip in my crotch as he tore open the gusset of my tights.
We stop kissing. Tom smiled and said, “I hope you’re ready baby… Here I come.” He pulled my thong aside and replaced his fingers with a thick juicy cock.
I let out a a loud screaming moan. “Ooohhh Daddy! Your dick is so fucking big!” I moaned in disbelief as his huge dick slipped in and out of my ass.
I had to go slow at first, but eventually got a good pace going. I rode up and down on Tom’s dick before he picked me up and bent me over on my knees. I turned around to see Tom’s stiff cock staring at the big gaping hole in my black tights, exposing my asshole. I felt him kneel behind me, pull my thong aside and squirt some lube on my hole. His dick slipped right back in and I felt closer to orgasm every time the tip of his cock massaged the walls of my ass. He grabbed the waistband of my ripped tights like horse reins, using them to fuck me deeper and deeper. At this point he ripped the toes of my tights open and was fondling my feet as he fucked me.
We were both moaning with pleasure and new climax was coming soon. Tom began rubbing my cock over my tights as he began to fuck me really hard. Then he said, “Oh Mischa, I’m cumming baby!” and his cock started pulsing inside my asshole, right as my little boy clitty began erupting inside my own tights.
“Yeah, Daddy. Cum inside me. I want it!”
We both lay there a while before cleaning ourselves up. When I got out of the bathroom, Tom had poured me a new glass of wine. I changed into a pair of grey footless tights and put my legs on his lap while we enjoyed another glass. As you can probably guess, he sucked on my toes and tore those tights open too.
It was a long night before I finally made it home.
