Sissy's First Gangbang

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more feminine the better. For a sissyhypno addict looking to explore their sexuality he seemed perfect. From the moment my lips wrapped around his thick hard cock the first time, I knew it was going to be more than just a one time thing. We've hooked up semi-regularly, depending on how hard I'm trying to fight the addiction at the time. Sometimes I see Daddy Larry multiple times a week, sometimes I let weeks go by. It's cool though cause I know Daddy Larry has other boys but he tells me I'm his favorite.

I'm just a normal guy when out in the world as my everyday straight persona. A little short but still average height (5'9), Slim but not anorexic (155 lbs) with a lovely but small dick just over 4 inches hard. It never impresses the girls, especially when seen flaccid, but it's still seen its share of action. Also I'm a grower not a shower as the saying goes, so when I'm not hard it's exactly what I'll call it henceforth; a sissy-clit. Over the course of our time together, I have gone from an occasional cocksucker to a full blown cross-dressing sissy cum-slut. This following story is why I believe Daddy Larry when he say I'm his favorite.

Earlier in the week I stopped by Daddy Larry's house for a quickie. A simple blow and go in his living room where he fucked my face for a few minutes while watching porn than came in my mouth. While waiting to watch me gulp down his thick creamy load, Daddy asked if I was going to be busy the coming Friday. Not thinking about it I quickly swallowed down that load and in that cum induced sissy bliss answered quickly that I had no plans the entire day or weekend.

So Thursday night, Daddy Larry texts me and tells me to be at his house at 3 pm, which is earlier than usual. I try to cancel out of it because having him on skype from when we first cam'd I had got the birthday notification from him that informed me Friday was his birthday. This for some reason sent off panic alarms. I worried Daddy Larry might try something romantic and ruin our pure-sex relationship. Boy was I wrong. Daddy firmly told me I had better be there and to bring a blindfold along with my usual stuff. I conceded cause the addition of a blindfold added a new level of curiosity. Why did he want me blindfolded? This was new. I decided I wasn't going to make a deal out of knowing it was his birthday though. I didn't want to bring a gift, not that I knew what he liked besides sissies. So I essentially already was a gift the way I figured it.

Friday afternoon shows up and I've gone all out. Full body-hair removal, Enema cleaning and a long relaxing bath. Afterwards I lubed up my smooth boi pussy real good and slipped in a small butt plug. I arrive wearing a tshirt and loose gym shorts over black lacy panties keeping my sissy clit sensitive but too constrained to get hard. In a small bag I have lip-gloss, a tie (for the blindfold), stockings, garter belt and hair scrunchies to turn my medium length hair into a more girlie ponytail. As I step out of the car and make my way up to the porch, I notice the sound of a lawnmower and look to the side of Daddy Larry's house. The noise is definitely coming from his backyard. Living on a corner with a diagonal driveway, I had pulled in not able to see that his gardener's truck and equipment were parked along the other street. Being afraid of any questioning looks as to why this young guy was at a much older guy's house, I rushed to the door and rang the doorbell.

I was so relieved when Daddy Larry answered the door and let me in but he had a grin on his face as he closed only the security screen door. Daddy Larry stood in the entryway in sweatpants and a t-shirt as he ordered "Let me see them." I knew right away what he meant and hesitated while nervously looking to the windows and then over my shoulder at the door. If any of those gardeners came around the front in that moment they would clearly see me slipping my shorts down, revealing my panty-clad ass for Daddy Larry. Thankfully none happened by during that moment but I had to admit it had my sissy-clit straining against the restrictive but soft material of my panties.

"Good boy. Daddy likes the panties you picked out. Lets see what else you brought, slut." His compliment followed by the authoritative request made my sissy-clit tingle more. He walked away, leaving me to close the door and then follow. Knowing just what Daddy Larry meant though, I nodded "Yes Daddy." and went off to his guest room to change into my full on sissy ensemble. The whole ordeal of almost being seen by strangers had me shaking and I took longer than normal to get ready. Thankfully the sound of the gardeners at work outside ended which helped settle my nerves. I love being a sissy slut for a man I met anonymously online but the idea of a random stranger from the "regular world" even just seeing me like this fills me with anxiety.

So after all is quiet, I finally come out and I'm feeling like such a slut with a butt-plug hidden under my panties, garter and stockings. My sissy clitty had already made a visible darker spot on my panties from leaking in excitement. Daddy Larry was waiting at his kitchen bar counter with a drink in hand. He motions me over and I timidly approach Daddy Larry who sets his drink aside and holds out his hand for the tie. I put it in his waiting hand and then he gestures me to turn around.

I back up towards my daddy and just before he brings that improvised blindfold over my eyes, I see the silhouettes of three men moving about the backyard through the half-closed blinds of the big bay window. My vision goes dark, but I had seen them, which meant if they really looked, they would see me! A blindfolded flat-chested sissy in black panties, garter belt and stockings ready to serve this older man. As the anxiety began to build up, I was about to object but then came the familiar firm hand on my shoulders pushing me down to where Daddy Larry wanted me. On my knees. There in the kitchen, with blinds half-open, Daddy Larry's strong hand moves from my shoulder to the back of my head, pressing me into his bulge covered only by sweatpants.

"No hands. Just your mouth, slut." he orders and I again I know what he wants but I hesitate in answering as I'm still thinking that one of the gardeners might glance in and see. Daddy Larry isn't very patient though and seemed to know exactly what I was scared of. "Don't make me repeat myself!" Daddy Larry raises his voice and even though it added to my anxiety, it snapped me into sissy submission. I also knew the longer I took, the louder and more verbal Daddy Larry would get. So blindfolded, I took a few tries before I got a good grip with my teeth on the waistband of his sweatpants. Inhaling that musky scent of a real man had me desperate to taste that daddy cock when I finally pulled them down enough for it to spring free.

I discovered quickly that robbing yourself of one sense can heighten or at least make you more aware of your other scenes. The smell, the feel and the taste of Daddy Larry's big thick cock-head slipping past my lips in the blackness was like reliving my first time sucking cock but in a new way. I explored the fat mushroom shaped tip with my tongue, teasing it for more drops of that salty sweet pre-cum daddy was already leaking. Feeling his hand on the back of my head again though, I knew Daddy Larry wanted more. I wanted more too, and it showed as I sank my mouth down until I had taken half of his shaft into my mouth. His thick head of his cock pushing at my throat gags me but doesn't stop either of us. More pressure is applied to the back of my head after daddy sees me catch my breath. My eyes start to water as daddy holds his cock lodged down my throat for a second or two then lets go. I pull back until I only just barely have my lips on the tip of his cock.

Saliva and pre-cum string from the tip of his cock to my lips and even though I can't see it, I can feel it. And so like a good sissy I lean forward, taking that cock right back into my hungry mouth. I slurp up the mix of pre-cum and spit, all the while bobbing my head back and forth, up and down on daddy's dick. "Oh yeeeeah, suck that cock. That's a good mouth you have, boy. Choke on it, slut!" Daddy Larry always spurs me on with his filthy dirty talk. I normally respond but with a mouthful of his cock, all I can do is let out garbled moans of approval. I keep sucking and Daddy keeps encouraging me with both the firm hand on the back of my head along with more dirty talk. All the usuals. Cocksucker, whore, sissy, faggot. Each one he calls me just makes me more eager to live up to those humiliating and degrading names.

"You hungry for a big load boy?" I eagerly nodded and mumbled some garbled attempt at "Yes daddy" around that hard cock. I keep sucking his dick with the cock-lust only a sissy knows. I am so desperate to make my daddy cum and taste his seed that the muffled voices speaking in Spanish almost go unnoticed. Almost.

"Keep sucking. Gonna fill you up tonight." My daddy demands and while I don't dare let his cock fall from my mouth, I freeze. I don't speak Spanish so I have no idea what is being said but one thing is clear. The voices are right at the backdoor, next to that big bay window with it's blinds only half closed. I panic but I can't object cause daddy's firm hand is still on the back of my head, keeping half of his cock still stuffed in my mouth. I hear what sounds like a question followed by laughter and then a sound that made my heart skip a beat. A knock. Daddy's hand on the back of my head becomes more forceful as he anticipated my reaction to the next words he spoke. "We're ready. Come on in."

The doorknob turned first and I fought harder against daddy's pull until he let go. His cock slipped from my lips the moment the door opened. There I was, blindfolded, mouth open with pre-cum and spit hanging from my lips in nothing but black panties, stockings and a garter belt. Whatever objections I had were erased by the realization that three men who I didn't even know what they looked like, were seeing me like this. I was a deer caught in the headlights.

Not that it would've mattered, I didn't even turn my head their way. Daddy's cock brushes against my lips as he starts to speak to them causing them to laugh. "Manuel, see I told you.-..." Daddy Larry switched over to his limited Spanish here and I again was left both literally and figuratively in the dark. Again more laughs came from behind me but I remained as still as a statue. I felt Daddy Larry's hand slide down the back of my head and reach under my shoulder pulling me back up. He pushed out one of the stools and walked me over to stand in front of it.

"Bend over, Joey. I'm giving my gardeners a treat today." My face must have turned a very bright shade of red there as he used the version of my name I identify as my sissy self. I wanted to object but again I was at a loss of words. I could not believe this was happening. Instead I seemed to enter a sissy auto-pilot mode and leaned forward on the stool, bending over it and sticking out my sissy bubble butt that was covered in lacy panties. Again there were laughs from behind me along with more Spanish words I didn't know although I recognized several as slang you sometimes hear and know are offensive but don't know their meaning.

Bent over a kitchen stool displaying my panty-clad ass to Hispanic gardeners that were total strangers was something I never ever imagined experiencing. It was the most humiliating and embarrassing moment I had ever experienced, until Daddy Larry gave more instructions. "Pull your panties down and show them your plug, sissy." Again I felt my face flush but I was starting to think Daddy Larry was just showing off that he had control over some young guy to his gardeners and that if I just got it over with, they would leave and we would continue on like normal.

So reaching back and hooking my panties from underneath the garter, I tugged them down until they were bunched up above the stockings and stuck my ass out. I knew the black end of the butt plug was clearly visible now and again the feeling was overwhelming. More Spanish words along with laughter was my reward for my submissive display. Their conversation among themselves quieted and one, who I believe was Manuel, addressed my daddy with slow but understandable English. "50 for mouth? how much to fuck?" he asks Daddy Larry and the reality of the situation set in. I started to stand up but my daddy notices and brings his open palm down hard on my bare ass. The slap is harder than normal and the first sound escapes my lips since the gardeners entered. I let out a quick cry of shock and pain at how hard Daddy Larry spanked me. "I didn't say to move, slut. Stay right there so Manuel and his friends can make their decision." he warns me before I feel his hand on my ass-cheek that was still stinging from his slap.

"Well you will have to use a condom to fuck the puto's pussy..." my daddy said to the gardeners as he unfastened my stockings from the garter belt. He then slides my bunched up panties all the way down my nylon covered legs. Next he runs his strong hand up my backside until he reaches the end of the butt plug so lewdly sticking out. He pulls and at first my sissy-cunt held on tight to the plug. Daddy Larry kept pulling though and finally the base popped past my sphincter and the whole thing slid right out. Not a huge plug, it still left my little puckered hole momentarily gaping just a little bit before I clenched it shut. I whimper at the sudden emptiness and shame that is overwhelming me while my daddy goes back to pimping me out. "50 for the mouth, 75 to fuck, or 100 for both." Daddy Larry offered then tried to repeat the deal in spanish it sounded. Again the gardeners seemed to hold another conversation among themselves before one spoke for the three of them. "Both, both and mouth." he says which was confusing to me until I realized he must've been gesturing to his friends for the other two answers. This meant two of them would fuck my ass, and that I would be sucking all three of them.

I didn't know what to say, or what to do. I had never been with more than one man, or even woman, at a time. I had never had a threesome but here I was about to take on three strangers and my daddy. Lucky for me, I didn't need to say or do anything as Daddy Larry took charge. He pulls me from the stool and again I am guided to my knees but I know I've been spun to face the trio of gardeners. More Spanish words were exchanged between my daddy and the gardeners before anything was remotely explained to me. "Okay slut, you're gonna take turns sucking their cocks getting them nice and hard while I make sure your boi pussy is ready for them." As Daddy Larry is telling me the plan, I can hear belt buckles, jeans, shoes, etc being removed and know these three strangers are stripping down in preparation to use me like a cheap whore.

I hear daddy move away, presumably to get more lube and/or condoms for the others but the gardeners waste no time once their clothes are off. I hear a phrase they end up repeating a lot, "Chupa mi pito" one of them says to me and then I smell it a moment before I feel the long but still semi-flaccid cock slide across my cheeks. The tip pokes at my somewhat parted lips but I don't immediately start sucking like I normally would when presented with a cock while in sissy mode. I was completely unprepared for the scent of another man's musk, especially after working out in the sun all day. I wanted to insist they shower first but before I can, the other two guys are presenting me with their own pungent scented manhoods and smearing pre-cum on the sides of my face. More laughs and Spanish slang that sounded like taunts come from them before Daddy Larry finally returns.

"What are you waiting for slut? Open up. Work the other cocks with your hands." he orders from behind me causing my lips to finally part all the way. With an open mouth as an invitation, whoever was in front pushes their cock forward and into my waiting mouth. The salty sweaty taste is overwhelming at first but as the man's cock hardens quickly in my mouth I grow used to it. My two hands reach up blindly for the other two men's cocks and try to stroke them as I suck the first man. Porn-stars make this look a lot easier than it is. The blindfold certainly didn't help either but eventually I got some kind of rhythm going. Just when I was starting to get a hang of it, bobbing my head forward on one cock while jerking off a cock in each hand, my Daddy joined in.

A cool slick finger at my sissy-cunt reminds me that daddy was gonna get my hole ready for two of these strangers to fuck. He pushes up more lube into my boi pussy and then works his way up from two fingers to a third. I begin to gyrate my hips into daddy's fingers all the while moaning around the first gardener's cock.

"How's that mouth, Manuel? Better than your wife?" my daddy asks the man who's cock I am sucking and repeats a few of the words in Spanish. "Si si, ..." Manuel answered continuing on in Spanish and making his buddies I was jerking off laugh again. I was starting to finally let myself get into the depravity and perversion of being the star of my own gang-bang. I quickened my pace on Manuel's cock, causing him to hiss in pleasure as I blew him. I could feel Manuel's member growing harder as I took him deep down my throat and held him there. He suddenly gave a grunt and thrusted forward, lodging his cock even deeper down my throat before it spasms. Hot and salty cum floods down my throat forcing me to gag and pull back from his cock. Instinctively I gulp down as much of the thick hot creamy semen that I can. His massive load fills my mouth but some escapes my lips, dribbling down my chin.

I pant for a few seconds, letting it sink in that I just swallowed the cum of a man who's face I've never seen. Before I can come to terms with the first load, the guy on my right is forcing me to turn toward his cock. Soon another cock is pushing at my lips, and although its aroma is strong too, I don't hesitate this time. The taste of the first man's cum is still strong in my mouth, making me suck the second's with a little more fervor. I expertly work my mouth up and down on the second gardener's meaty shaft. His cock wasn't as long as the first guy, but it was thick and I had to keep my jaw stretched wide to give the man the best blowjob I could. His cock pumped into the back of my mouth as pushed down to the base. He begins to thrust in time to me bobbing up and down on his cock, forcefully fucking my face and making me gag.

"Oh yeah fuck that sissy's face! She loves it!" Daddy Larry encourages from behind as he continues to play with my ass preparing it for cock. While I was loving it, I knew my daddy must've been loving it even more. Daddy Larry often puts on Facial Abuse porn when he wants to just get off quickly, so a live show was really getting him going. The guy fucking my mouth didn't really need the encouragement though as he was just about at his limit. Putting his hands on each side of my head, he begins to brutally push and pull my head up and down harshly on his throbbing cock. I gag and gasp for air but I can hear this only exciting him more as he muttered more Spanish slang at me. Then the second gardener forces himself deep and I feel his spasming prick shoot spurt after spurt of hot jism down the back of my throat. I swallow it down as he continues to groan but then finally releases his hold on my head. His cock slowly slides out as I can finally turn my head again. I'm out of breath with cum on my lips when Daddy announces, "Okay she's ready to take one in each end now."