doc-mccockin | Dec 24, 2025
good thinking, making him cum and swallowing his load will make him forget what he was getting suspicious about ;)

ciao69 | Dec 21, 2025
*There I was... cum all over my stomach... three weeks worth.*
Hahaha!!!! I knew I could break you. Once I found your Imagefap, I knew how to get you!!!! Sissy stuff!!!! Ha!!!!
Now I only have to not cum for one week.... and YOU lose the bet!!! And I can do that standing on my head!!! Especially when I know you've blown your load already!!!!
You can pretty much start shopping for your Harley Quinn costume now!!!! Oh damn!!!! I'm so looking forward to this!!!!
*You slammed the door shut and I could hear you laughing as you walked away*
Fuck!!!! FUCK!!!!!!!
*I had one week to get him to cum!!! At any cost!!!!*

Beau_peep_69 | Dec 21, 2025
The next week went by slowly. You couldn't think or focus on anything other than the stupid bet. You decided to call in sick from work and just focus on really trying to make him crack. He was still playing the porn everywhere and sending you pictures, captions and videos, all of it sissy stuff so you figured that was probably the trick to getting him. You started responding with your own porn, shit you found, even some of your favourites you'd found along the way. Suddenly sharing the sissy stuff you'd been hiding was really hot. You'd been tentative admitting liking it before but now you had been caught it was kind of freeing.. no.. arousing. It was hot that someone knew you were into something so taboo. You couldn't help yourself, and given that you'd already lost no nut November there was no harm in jerking off. So you did. You'd send him a video or some lewd pictures and the . immediately whip out your cock and start jerking off. Soon he'd get horny too and pull out his cock and join you. But he wasn't getting close to.cumming. you on the other hand. The more he tailored the porn to hot sissies getting fucked the hornier you got. You'd be on the edge of orgasm. Soon your eyes were wandering too from the porn and to that long hard dick he was stroking slowly and determinedly. You had to make him cum.. you wanted him to cum.. fuck just cum already cum for me! Wait.. no.. cum and lose the bet... That's right... You figured if it was making you so hot and bothered it had to be effecting him too. But clearly there was something missing.. maybe he needed a bit more coaxing..some extra visuals. He watches porn almost every waking second of his day.. so maybe he need something more.. tangible. The sissy videos playing on almost every screen of the house had been telling you for weeks to dress up as a girl, to wear panties, stockings, make up, a pretty dress and heels. You were starting to think it was a good idea. With only days left to make your roommate and best friend lose this bet you had to do something drastic.. you left the house for the first time in days and wandered to the local shopping mall. You were just buying some cute things for your girlfriend's birthday, that was the cover story you went with. Your phone continued vibrating as your roommate sent you caption after caption about Sissies losing bets and having to dress up in slutty outfits. Subconsciously influencing your decisions all the outfits you picked were decidedly on the skimpy or slutty side. As soon as you got back to the apartment you tried one on, relishing in the feel of the girlish fabric. You were more turned on than you ever have been and immediately started jerking off. Your roommate saw you and quickly came out to join you on the couch releasing his huge cock. Between the feeling of being dressed up like a woman and the huge cock slowly being jerked off in front of you you were lost in lust. The porn on the tv next to you entirely unnecessary as you watched your roommate's cock intently and stroked your own little dick through your panties. You just wanted him to cum so bad. You needed him to cum. To make him cum. You only had days left.

mesmomite | Dec 20, 2025
The straightest part in when he sprays my face with spunk and leaves me begging for more

Beau_peep_69 | Dec 20, 2025
Absolutely when you're done exercising, spending hours pumping hard in the gym, its totally reasonable and straight for your best bud to give you some protein and vitamins to help your muscle growth. Given that your face and mouth have been doing all the working out it only makes sense. It's the manliest thing you can do to get a face full of testosterone filled protein, why wouldn't you beg for more and more and more. Maybe he should just inject it straight into you next time.

mesmomite | Dec 21, 2025
My buddy knows that I’m happy to take his protein shot wherever he chooses to put it. On my face, all over my body, in my mouth, up my ass, all he has to do is point and I’m in the right position to take that testosterone filled load

ciao69 | Dec 22, 2025
You were were landing at the big airport in the city. You said you were gonna take a cab home, but I wanted to surprise you.
I had gotten so good at applying make up, I pretty much looked like a woman. I was dressed to the nines -way too slutty for the airport!
I even had a big sign with me "Welcome home, Beau!!!"
I waited there like a giddy schoolgirl, I couldn't wait to see your face!!
Inside I really hoped all the stuff we'd been doing was.... well... real....
Did you really want to do all those things to me? Or was I about to make an absolute fool of myself??

Beau_peep_69 | Dec 23, 2025
The flight was long and tiring, some crazy bitch had been fighting with her husband for the whole flight and kept us all awake. Just before we landed she decided to add assault to the disturbance violation she'd been slapped with and as soon as we landed the police stormed the plane, cuffed and removed her after having to taze her twice and dragging the screaming husband who now had a freshly blackened eye. A simple disembarkmenf became two hours of conflict and agony. Out of it I trudged my way through the baggage claim and came out into the arrivals hall. I almost didn't see the sign but had a double take. Admittedly not due to the sign but due to the absolute smoke show holding it. A petite woman dressed like she was about to go to a club or a brothel with a make up look that screamed 'fuck my mouth' ruby red lipstick, smokey eye make up deep blush in that egirl anime style. She was like a gonners heaven. Noticed her smiling at me and I looked away embarrassed at being caught staring before I turned back to her. The sign said my name... Wait... I recognize some of that outfit. "Holy fuck... Walt?... Uh. I mean.. umm Wendy?" I yelled out, correcting myself as people started to look towards us. Quickly realizing you looked nothing like a Walt anymore. My buddy was hidden behind a very well crafted woman. "Jesus.. I know you've been dressing up as a joke for our chats and stuff while I was away but.. holy shit is that really you? You're not some hooker my friend hired to prank me or something... Uh.. no offense I mean.. if you are actually a chick. Fuck me... I'm tired.. this is... a lot... Can.. can we continue this in the car if you're driving me home or something." I stumble through and then grab your hand trying to lead you to the exit. Your hand is so soft and you smell amazing, sweet and floral. It's been so long since I'd touched a woman. I feel my pants tightening as an erection forms. I try to hide it with my bag as we walk forward. "So uhh.. thanks.. for coming to get me and .. uhh putting in all this effort. You.. you look great.. amazing.. umm good yeah something"