I was lying in bed after my shift, I replayed the events of the day and how I was lured into the cell with Yolanda. I could have left her cell many times but deep down I seemed to want this. Why? Why now in my life? Was I always interested but kept it in my subconscious so I wouldn't have to face it?
I never considered myself gay, in fact, never even crossed my mind, despite hearing people say, "everyone thinks about sucking dick at least once in their life", but not me. But now I not only thought about it but I actually did it and if I'm honest, I kind of liked it. This was hard for me to process because I always considered myself a typical red blooded hetrosexual american kid, I was a 3 sport athlete in high school, I served in the military before applying to be a corrections officer and always dated women. Nothing in my past would suggest, or even hint, that I was queer. I drift off to sleep trying to make sense of this and more importantly, wondering what I'm going to do tomorrow at work.
"Is my girl wearing her panties like she was instructed? Yolanda questioned.
"Yes" I said quietly, trying to prevent anyone from hearing.
"Does my little girl want to come show mommy her new panties?"
I pull out my keys to open the door and let myself inside. I stand in front of Yolanda not knowing what to say or do so I keep my head down ashamed.
"Go ahead, let me see your cute ass in those panties...I know you want to model them for me"
"Oooh, how sexy, do you feel sexy? I bet you do and I bet it feels nice against your skin, doesn't it?"
I stand there frozen not able to speak or move but my dick is starting to tingle and I feel it getting hard.
"Is my baby girl shy now? Cat got your tongue? I can give you something you can put that tongue to work on. Is this what you want?" As she pulls down her prison issue jumpsuit to show me her bulging cock in her panties.
I take a step forward and extend my hand to reach for her cock but before I can grab it she says,
"No, no, no...you remember you need to ask my permission to touch my cock, remember?"
Something in me screams that I need to get my hands on this beautiful cock, I can't think of anything else at the moment..."Can I please touch your cock Yolanda?" I plead.
"I don't think you are ready yet, let me get some lipstick for those cocksucking lips of yours"
Without resisting I let Yolanda pull out lipstick and start applying it to my lips. Then she tells me to close my eyes as she pulls out eyeliner and starts applying it to my eyes. I feel her cock rubbing up against mine through our panties, it's getting me turned on as my dick starts to dart straight out from me. She intentionally sways her hips to rub on me some more while she continues to add some blush to finish the look.
"There you go, such a pretty girl...does Tracey want to play with me tonight?" She coos.
I nod up and down while staring at her big cock bulging in her panties prying to get out.
"Go ahead girl, get down there and give your momma's cock a little kiss"
I slump to the floor and pull out her cock...I stare at it for a second and then rub it across my lips in admiration. It feels so good as it slides back and forth across my lips, I'm savoring the smell and feel before I dive in.
I open my mouth and give it a gentle kiss followed by a lick up and down the shaft. Then I feel her thrust her hips forward and "POP", her cock forces entry and slides deliciously into my mouth. I start sucking like a dog in heat, slobbering over this wonderful dick and then I hear footsteps. I try to rise but Yolanda has the leverage and pushes down on my shoulders keeping me on the ground. I try harder to move away but it's no use, I hear,
"What the fuck are you fags doing in there you?" The guard yells
I recognized the voice, it was one of the guards named Mike. Mike was this arrogant prick that thought he was god's gift to women. He'd always bragged about how many girls he fucks and how they are all sluts. He also hate gays and would make fun of the femboys in prison by calling them fags or cocksuckers. He seemed to relish being a dick to them, it made him feel powerful.
As he gets closer his eyes and mine make contact and he realizes who I am and that I'm on the floor sucking a cock.
"You fucking fag, if you want to suck cock you could have just came to me, get over here you sissy bitch so I can give you something to suck on" He orders.
Beeb, Beeb, Beeb...I awake to my alarm going off...I feel my cock ready to explode so I quickly start to jack off but instead of thinking about Yolanda I was now focused on Mike.
I imagine him standing over me while I'm sucking his dick. He's taunting me by calling me names...
"That's right you faggot, suck my dick like the queer you are. You are gonna be my bitch from now on aren't you?"
I can only nod as I continue to suck his dick.
"Yeah, keep sucking...Who's my bitch?" he asks rhetorically.
"I can't wait to tell the guys about this, they won't believe me that you are a cocksucking fag...and you are even wearing panties, what fucking sissy" He chuckles.
I couldn't take it anymore, I exploded with cum shooting straight up landing all over my stomach. I continue to stroke my dick to get every last drop out still imaging Mike laughing while standing over me slapping his dick across my cheeks.
Holy fuck, that was intense. I could feel my muscle that runs underneath my balls tighten and lock up like an engine that seizes, I couldn't get it to relax. My legs are buzzing from the orgasm and I feel my heart pounding out of my chest.
I try to focus, and as my muscles start to relax thoughts run through my head. Shit, what was that about? Mike? Really? I thought he was such an asshole yet I was on my knees sucking his cock like some homo in a porn theater. Clearly I enjoyed it as I came so hard that the spasms in my groin area had frozen in the contradiction state. Why did that excite me so much? I'm still trying to figure out the whole Yolanda thing and now I got this sexual thought of Mike dominating me while I'm wearing panties.
I get up to jump in the shower, I have a few hours before I need to be at work. As I'm showering I'm thinking about what I should do. If I was to listen to Yolanda I would have to go buy some panties from someplace. But if I decide to not do that I risk her telling everyone about us. And if Mike gets a whiff of even a rumor to that effect he will ride me constantly. I can hear him now, "Hey Terry, I understand you give the best blowjobs, bring your faggy ass over here and I'll let you taste a real cock".
I feel myself starting to get hard again...I don't normally have the ability to reload so quickly, ironically it was one of the things my girlfriend and I argued about. She loved to fuck but I tried to explain to her that it's different for guys, we need time to recharge our batteries so to speak. But she was a nympho and told me her last boyfriend didn't have that problem, she then would question if I was even attracted to her if I couldn't get hard minutes after we just had sex. It was all bullshit of course but she didn't get it and eventually it led to us fighting about other stuff and eventually breaking up.
I reach down to grab my dick while the hot water runs down my back. I continue to think how Mike would love making fun of me if there was a rumor about me and Yolanda. It doesn't have to be true for Mike, he thinks he's a badass and the funniest guy in the department so he would look at it as an opportunity.
"That's right faggot, suck that dick like a bitch...I should hand you over to the Bloods (the reigning black gang in our prison), they would love to have a sweet piece of ass like you to fuck."
I'm stroking my cock in full force now thinking how I would be passed around the other inmates as a sex toy for their use.
"Maybe we'll get you some high heels and a mini-skirt for you to wear around the cellblock, you'd probably like that wouldn't you faggot?"
For the second time in the past 20 min I shot cum over my hand and the shower floor.
I start plotting out my day as I get dressed. I think the prudent thing to do is go find some panties to wear so I can avoid Yolanda telling everyone that I sucked her dick, especially Mike. I'll need to go somewhere where they sell both men and women's clothing, that way I can buy a few things and sneak the panties in with the other items.
I head over to the mall, I go into one of the department stores there which sells everything from appliances to toys and of course women's undergarments. I start in the men's section grabbing some underwear, t-shirts, and socks, all of which I need anyway. I meander over to the women's section, trying not to look suspicious. I casually walk around the area pretending I'm not paying attention to anything in particular.
I spot the area where the panties were, I see a pink pair right away. As I reached the panties area I took a quick look around, I felt like a burglar looking to see if anyone was watching me trying to break into a car. I look back at the panties and I see all these sizes, shit, I don't know what size I am in women's underwear. Obviously I can't ask someone so I look for and grab the biggest pair I see. I don't even bother holding it up to gauge if it would fit, I just throw it in my cart with the other things I got.
I looked for a register with someone who looked clueless. I definitely didn't want to go to some young girls lane...I spotted an old Indian man who looks about as happy as I am to be here. Thankfully I guessed correctly as he barely even looks at the items he is scanning. He bags them up and I quickly head for my car.
Back at home after eating my lunch I start to get ready for work. As I'm standing in my bedroom I look at these panties, I'm still not sure I can put these on, it seems so wrong. After stalling for a minute or two I pull the panties up over my crotch and ass. Surprisingly they fit pretty close, a tad small but passable. I did feel my ass cheeks hanging out, a combination of the cut of the panties and the fact that they were probably a size too small.
These feel great I admit to myself. So silky and smooth on my dick, I like the way that feels. I walk to the mirror to check out what they look like. My dick is rubbing against the sheer fabric as I walk, I can feel my dick start to stir. I stop to look at myself in the mirror, I look like an idiot but I can't think of another option at the moment.
I finish getting ready and head to work. As I pull up to park I see Mike getting out of his F150 truck. He gives me a head nod as a hello and I give him a slight wave of acknowledgement. I sit in my car for a minute while I watch him get far enough ahead of me before I get out. I'd rather avoid him for the time being, especially after that wild dream.
I do my regular rounds and know I'm going to have to confront Yolanda at some point. I'm hoping if I wait to walk by her cell that it will be late enough and she'll be fast asleep. I take my dinner break, I still haven't gone by the tier where Yoland's cell is but after the break I can't avoid it any longer.
I think about what I'm gonna say if she is up. Maybe I'll simply say hi but as soon as she starts to engage in conversation I'll fake like I'm getting called to an emergency in another part of the cell block. It's pretty easy to key up your mic without anyone noticing, they'll hear the static and the chirp from the radio. Typically the inmates are so used to hearing that kind of chatter that they naturally block it out so I doubt Yolanda would even know that no one actually called for me. I like this plan as I continue towards Yolanda's area.
