Recently I started talking to a young sissy who had been dumped by her bf and left stranded out of town. I didn't have work that weekend so I offered to pick her up. It was a 5 hour drive but I didn't mind since she offered to show me a good time.
I booked a room in her name so she could get ready for me once I arrived in town. When I got to the hotel and when to the room she greated me in panties and a bra. Smooth, shaven and her 4" clit already in attention I let myself in and kissed her passionately. Reaching down I rubbed her clit and she fumbled around to get my belt off and pants unzipped. The moment my hardening cock was free, she dropped to her knees and began kissing and licking my cock until I was at full length. As soon as I was, she hungrily swallowed my entire length and began giving me one hell of a bj. I watched as her head bobbed back and forth occasionally she'd back off to lick the underside of my shift and put my balls in her mouth. She was a natural cock suckered and it didn't take me long to blow my load down her throat. She never stop that vacuum seal on that mouth and swallowed every damn drop.
I motioned for her to lay on the bed with her head off the edge. I turned around and opened my cheeks and made you rim my asshole. Gawd was she a nasty freak, she dove in like a woman possessed and it didn't talk long for my election to be back.
I flipped her around and got behind her on the bed. Grabbing some lube, I put some on her tight ass and on my fingers. I started slowly probing her hole, starting with one finger and adding another as soon as she loosened. Soon enough she had four fingers stretching that tight hole. I knew she was ready so I luded my cock and with one long stroke, shoved my cock deep inside her. She let out a loud moan and buried her face in a pillow. She was breathing heavily while she adjust to my size and I pulled back and gave another hard shove. Her nails dug into the sheets as she whimpered and buckled slightly.
"There's no getting away, my dirty slut," I groaned.
I started fucking that tight hole in a primal fury, she tilted her head to the side and said "YES DADDY, FUUUUUUUCK ME!"
I leaned forward to bite at her neck and she took one relentless thrust after another. Her muffled screams only driving me to fuck her like the slut she was. My fury gave way to euphoria as my cock shot several warm loads of cum in her. Her muscles almost seemed to milk every drop.
I fell to the side as she got up and began cleaning my cock with her dirty mouth. I was nearly limp when she finished licking my up and she lay on my chest. "Whats next," she said lovingly.
"Well I booked the room for two nights, so we can have lots of fun before we head home.," I replied.
The next two days were something I will never forget. Nikki and I eventually lost touch last year after she relapsed but I will never forget those two days

She was shy and timid when we first started talking online. Still frightened at the idea of coming out publicly, I assured her that she was in good hands. It took a few weeks of late night texts to become at ease with who she really was and one night she asked to finally meet. I had reserved a hotel room and bought her some toys and a few outfits. I left the room and hit the bar as she got herself settled in the room. After a text saying "Come up, Daddy." I closed my tab and headed to the room.
As I walked in and saw laying at the foot of the bed dolled up and sexy as hell, I was hard almost immediately. She'd blindfolded herself and lay there breathing nervously. I stood before her and watched as she unzipped my pants and pulled out my cock. She took her time rubbing it and caressing my balls before she licked the tip and moaned as pre cum hit her tongue and she liked her lips before proceeding to deep throat my cock. The warm sensation of her mouth nearly brought me to my knees. She sucked me better then I'd ever been sucked in some time so it didn't take long for me to drop my first load deep down her throat.
It took a minute to come to before I realized that Amanda had taken the vibrating butt plug I'd bought her and already used it to help stretch her virgin hole. I brought a chair to the foot of the bed and had her spread her ass in front of me. I began licking her ass with the plug still vibrating and stroke her little clip. She really enjoyed that as she brought a pillow to her face and moaned loudly. After she squirted in my hand I got her onto the bed and pulled out the plug. Lubing up her hole I started to finger her, first with two fingers then with three. After I felt she was ready, I pinned her ankles above my shoulders and preceeded to slowly penetrate her tight hole. Even with the stretching and lube, her hole was extremely tight and resistance was met until finally my entire length was deep inside her. She whimpered and moaned for a bit until she became used to it and soon my thrusts became easier and she cried "Daddy." I made my pace slow at first but soon lust over took me and needed to pound this ripe cunt into submission. We fucked several time that night and a couple more before check out. We made plans to meet up next month and she wants to bring a friend to submit to the two of us, guess next month is gonna be fun

So a month ago I met a filthy little cunt online and we hadn't had a chance to play due to her school and my work. Then she found out her roommates were going out of town for Labor Day weekend. She'd kept her lifestyle secret from her college friends so she was eager to shed her false persona and be treated like a real nasty slut. I got to her room late on Friday night and was delighted to see her dolled up and on her knees. I locked the door behind me and stood in front of her, she rubbed my crotch and felt me getting hard. She proceeded to unzip my pants, pulled my cock out and began licking the tip gently. Precum already oozing out she hungrily shoved my cock down her throat and proceeded to suck my cock like a good girl. Only took a couple minutes for me too shoot my hot load down her throat as she massaged my balls and swallowed every drop.
We then went to her room where i got her on all fours and began spanking her. I worked her up til she was able to take some pretty hard slaps. My cock now hard again I decided to coat with lube and begin working her tight hole. She'd only done this once before with a guy half my length and judging by her toys she was due for some pain. I worked her whole for sometime before she was able to accommodate my entire length but once that happened I began vigorously pound this cunt. She cried and whimpered as she buried her face in the pillow. She began to spasm and exclaimed that she was cumming, she was not allowed to so i reached around and squeezed her clit so tightly that she let yelped and buckled. "DADDY CUMS FIRST, BITCH" I exclaimed as I pounded harder. I fucked her for another 10mins before I shot my load. She came twice despite my trying so after i forced her to lick my cock clean with her tongue, i then brought out my belt and punished her. She took it like a good girl. We played all night into the morning and I was happy to hear back from her that she wants to see me again.