I had this set up in junior college
My roommate comes into my room, jerking their cock, "I'm here to make a deposit" I roll onto my stomach obediently, pull my boxers down. They tug the plug out of my ass, shove the tip of their cock inside. A delicious stretch but not enough for me to feel good. This isn't about me. They jerk their cock, shooting hot ribbons of cum deep in my sticky ass, "good boy" they sigh happily as they pop the plug back in, locking their cum inside me and giving me a hard spank as they leave.
I was checking tinder for some sissy girls and swiping who i liked. After 10 minutes i got matching notification. We talked some and know eachothers. Then told me she was virgin. I said i popped so much cherry and thats gonna be okay. I said i can be your first. I asked for adress and drive there for meeting. Sissy opened door and i see a that cute sissy. She was skinny but curved. 20 years old. So feminen also she was shorter than me. I come inside and sit on couch next to her. We talked some while drinking something. She was so nervous about first time. I grabbed her thighs and started to rub for comforting. We were getting some hot there. I grabbed her tshirt and take off. Then unzip her pant slowly. Pull that pant down and see her tiny bulge first time . I said oh my god it is so small. I asked her did you see a huge cock before and she said only in porns. I pull out my huge cock beside her and she shooked. I didnt even full hard at that moment and still way too much bigger than her. I made her drop on her knees on front of me and made her suck my half hard cock. She said " its so big i cant fit in my mouth". I said try harder cutie. She made my cock so hard inside her mouth. I said now its time for your first time. She was shaking lil bit and nervous bc my cock is massive. I lay her down on her back in missionary position. Damnnn that view was so beautiful. Her tiny clitty trying to get hard down there . I rubbed her tight pussy slooowly and spit on my fingers for some lube. I said are you ready for your first cock? She nodded me and grabbed sheets tightly. I grabbed my cock and place it on her pussy. Pussy twitching like a crazy. Damnnnn girl. I pushed my hard cock inside pussy but it was so tight. After some trying my cocks head part slide inside. I looked her eyes and they are rolling back damnnn. She moaned so loudly while im going deeper and deeper. Then i close to her ear and said "you are woman now".
(via blackmanwhiteman, blackmanwhiteman)
Scramble my brain
If any one wants to talk to me and have me play out any fantasy just hmu
I do in fact know daddy