u/grandslmham

I have a good friend we’re in our 30s and we go way back. I’m talking friend since middle school. In our college days we did some wild things mmf , fucking in the same room we even swapped gfs once . One thing that has always made these escapades great is that he has a big dick. I’ve always been in awe of his big cock and as of late I’ve been exploring things like cuck, sissy , bi lifestyle . He doesn’t know this but lately because I’ve been so deep in the cock rabbit hole, it seems to be something that’s always in the back of my head .

The other day he invited me over to watch the dodger game with a few other friends that also go way back . It was supposed to be a decent group of people but most of our friends are in new relationships and so we’ve been getting a lot of last min bail outs . Game day was no surprise and it turned out to be just 3 of us and our third friend bailed early because he works nights .

Towards the end of the game we rolled a joint and started talking about the good ol days. One of my girl best friends dating him once and she mentioned that he had a big dick . Now we’ve both seen each other naked so it’s verified but for some reason I brought it up . He just laughed and we continued to watch the game . By the 9th inning I brought it back up again . I said something to the effect of “yeah man you had her souring with that monster of yours “. Soon as say that he lets out a sigh of frustration but immediately after just pulls down his basket ball shorts and takes out his cock .

It was just there soft but even so it was thick and juicy , he pulls my head towards it and I’d be lying if I said I put up a fight . I wanted it so I just put it in my mouth . I felt it grow in my mouth, it was heavy and squishier than I expected. I took my time getting it nice and sloppy . I must’ve sucked him for a good half hour I purposely slow blowed him till he came. I never made eye contact but when I was done I cleaned my self and just left .

I thought it would be weird but a day later he hits me up casually if I’m down for some tacos with the crew .I tell him yeah and he says that he will scoop me up . We drive to get tacos and it’s chill we have a casual conversation about what’s been going on and nothing is mentioned about the other day . We eat catch up with the rest of the crew like nothing ever happened . Although on the way back he does the same thing . Whips out his cock and like a moth to flames I willing go to him and give him road head, he cums just a few blocks from my place. It’s silent but not awkward he just turned up the radio . We get to my place he says peace out like we normally do and life goes on .

I feel like we’re in some unspoken arrangement where I’m his personal mouth whore.

M30 when I hit puberty my only way to get off was humping and grinding on things . For some reason using my hands felt taboo and humping like I was circumventing something. As I got a grasp on it I would find the softest of sheets or fabric to grind . I don’t consider myself good looking but I’ve never had a shortage of gf and when sex came into play the first time a hand was used to stroke my cock was a gfs .this continued for a long time . Even in college sex was amazing but again any solo things involved humping or using vibrators to get off. I’ve been exploring sissy hood for only a year now and I have too prior to this and still I was t a habitual porn consumer . But I have to say that cock has always been 50/50 part of my turn ons I just didn’t know I was a sissy until my first sissy hypno where it all clicked .

For as long as I can remember (m30) I’ve been a pre bed toker. I usually unwind shower get comfortable roll a joint and veg out. But since I started dabbling in hypno a smoke session lately means I end up riding my growing flesh jack dildo collection dressed and watching hypno .

This friday I noticed something peculiar. I was out with my bros at a bar near my place ( they don’t know I’m a closet sissy ). After a few beers we decided to just go back to my place and chill. My apartment isn’t that big and I don’t mind if my homies go into my bedroom to crash or take calls from if it’s too loud in the living room .

Well this happened my friend Ray had to take a call and went into my room . We were chilling talking shit when Ray reappears holding my favorite panties and mesh body suit . I’ve been so into smoking and hypno the last few days I forgot to put it away . I’m turning red feeling caught and outed when Ray blurts out damn bro that’s why you’ve been MIA you’ve been getting some ass ?? (I am seeing someone but we’re not on a level where she can meet my friends just yet . It’s a bit of an undefined situation that I won’t get into.) Immediately relieved that he didn’t suspect I was dressing up I played it up like it was some freaky girl I met at work .

Of course they asked for the details of what she was like and for some reason my sissy persona was the person I described . The topic didn’t linger I got some love for my choice in freaky hook up and moved on . As soon as they left I cleaned up , showered got ready for bed and like clockwork lit a joint . Halfway through my session I get this craving to dress up . The humiliation of almost getting caught get me going . I get full dressed wig makeup the whole nine . I even invested in a led light and a mandala banner that I put up to pretend I’m in my sissy room .

Then I don’t know what came over me . I start taking sexy pictures ,me riding my dildo me posing etc . Once I’m done I lay down and start to vibe my cage while looking at my recent pictures . Then I’m not sure why I do the following but I send a picture of me dolled up wig and all from the back only to the group chat with all my bros . Then say “ look who dropped by after you guys left “ you can’t tell it’s me but I start to panic but it’s too late .

A few minutes go by my hearts racing and it feel like an eternity. Ray responds complementing her ass . Soon everyone else chimes in , all positive. When I get a little bolder and shows picture of my ass in a thong taking a thick dildo . My caption this time was she says she needs to be spit roasted but she likes them long and thick . Almost instantly everyone of my guy friends is proposing they are what she needs . So I say she says she’s going to need proof . My text doesn’t get to delivered fast enough when dick pics flood the chat .

At this point I’m stoned and super horny I’m sucking on my dildos teasing my guy friends with pictures taken at the perfect angle . I imagine them all taking turns on me . None of them where super large or hung but their cocks looks so good to me . I’m on the shorter more smaller frame as most my friends are taller and more fit. So to see my gym bro homies send cock and six packs drives me to leak like crazy in my cage . The night ended with me in the shower screaming out names of my friends pretending they were pounding me . I’m sure it’s unrealistic but a sissy can dream .

My gf (28) and I (30) have discussed cuckholding and my gf enjoys the dirty talk aspect of it but is in no way interested in sleeping with other men. But she’s recently found this mid ground where she finds couples where the man is well endowed , and we have sex in the same room as them . During the act she likes to admire the guys cock and make comments about how big and how well he fucks his partner. Sometimes stopping mid sex to just observe and masturbate . The last encounter she laid next to the girl in the same position and had me eat her out as the guy pounded his wife into multiple orgasms odd enough my gf would almost cum at the same time or right after .

When we do fuck in the same room as other couples she’s extremely wet and even eggs on the guys . Complementing them and begging them to fuck their partners harder. Then when we’re alone she will recap her favorite parts of the session while we’re having sex and will cum really hard . At times even calling out the guys names . I’ve asked her if she will like to participate and she tells me no that she likes this better. She’s definitely not hesitant as she sets up all these meet ups . I feel like I’m more humiliated than cucked. Long story short is this considered cucking ?

My new favorite part of being a sissy is ordering sissy things with the sole purpose of purging them after a weekend of using them.

On my first purge I found myself longing for particular dildos and outfits. So much so I was fingering myself while going through pictures and videos of myself using those toys and outfits. There was humiliation
factor to being incapable to cum as hard without my toys. The thought of needing my sissy things drove me wild. I was in so much sissy heat I couldn't sleep some days because my sissy pyssy needed to be filled.

Soon as I reordered my toys I would go crazy. That first few days back where intense. Since all this is expensive the gaps between repurchases are pretty long so I'm left to hump grind and finger until then next shipment arrives. I've recently added a mold of my pathetic small cock. That one I don't even purge because when I get desperate Its a reminder that my tiny cock can't satisfy a desprate sissy like me.