I was rummaging through my closet when I spied my old football helmet. It brought back memories. Though not what you might think. I was never on the football team, never a large strong guy, never talented in that way.
It was maybe five years ago, on Halloween, that I’d dressed up in a costume that included the helmet.
I’d worn women’s clothes: jeans, flats, wig, gloves, and halter top. On top of that, a football jersey, mask, shoulderpads, and the helmet. The effect was that I appeared to be a girl dressed as a football player. You see I couldn’t just dress as a woman: my shoulders were too broad, my hands too manly; I would not be passable.
But the first layer was me being dressed as a woman, then the second layer would hide the faults: a costume in a costume.
I did it because I was curious to try sucking a cock but had no other way to do it. With the costume, and some alcohol in a bar, the unsuspecting men were quite willing to plunge their cocks into my mouth.
I liked it. It was surprisingly fun to trick them as well – they all thought they were enjoying the mouth of a woman. While I enjoyed sucking cocks, the thrill from them being unwittingly fooled excited me to no end. Additionally, I liked being thought of as a girl.
Halloween was only a month away. Maybe I would resurrect the woman dressed as a linebacker.
A couple weeks later I was leaving the sporting goods store, as I was walking around the corner into the mall, there was one of those temporary Halloween stores that pops up.
The sexy mannequin in the window caught my eye. She was hot considering she was plastic. She was dressed in a furry cat outfit: lots of fur everywhere. She wore a crop top hooded fur jacket with built in cat ears. Then a fur skirt with matching fur around her ankles and fur paws on the back of her hands.
I was shocked at my own lusty reaction to a plastic mannequin. Looking closely I could see it would be better than my sports costume from so many years ago. My old costume had been crude and hobbled together like the costumes of cheerleaders I’d seen in college who borrowed their boyfriend’s football gear. In contrast, this was very professional and exploded with sex appeal.
The fur ankle things could be worn with any shoes and would hide the size of my feet which were a little big for women’s feet.
The fur paws would hide the size of my hands unless someone looked directly at the palms. They would also allow me free use of my hands.
Because the jacket was fur and had a hood it would hide the broadness of my shoulders.
She wore a bodysuit underneath, but I could easily see a lace bra working as well. Then my waist would be the only part of my skin showing. This was, coincidentally, the most feminine part of me.
On impulse, I bought it on the spot. I knew I would need to solve the problem of my face showing later. I arrived home while my wife was out and stashed it in the garage.
The cat outfit came with a tiny plastic catwoman mask large enough only to cover my eyes. With some searching online I found a soft furry whole-face mask that would allow a man to fuck my mouth without scraping on sharp edges.
I found time on several occasions to try it on and admire myself before Halloween. I even practiced putting my wife’s sex toys in my mouth to test it out. This was definitely going to work.
For the next part of my plan I sent myself an email, which appeared to be from ‘corporate’, requiring me to choose a date to go out of town – either on Halloween or our anniversary. It was easy enough to leave my computer screen open so she would accidentally see it. When she did, she demanded that I attend on Halloween.
Of course, I didn’t go out of town. I just booked a room in a hotel where the bar was having a large Halloween party.
Halloween afternoon, my wife, Aimee, dropped me off at the airport where I did not board a plane, but quickly caught a cab to my hotel thirty minutes away.
I laid out my outfit thinking about tonight. I got dinner in the hotel restaurant, and happened to see a bottle of perfume at the gift shop I thought would help solidify the illusion – so I got it. Then I got the bright idea to get hand lotion to soften my hands too.
I consider myself to be an occasional crossdresser, having done it that one time before five years ago, and not a tranny. Though I had read a guide for transvestites once since then, which had the most helpful tip: a man’s voice only sounds that way when he speaks out loud, a whisper sounds the same whether it comes from a man or a woman.
So unlike that time so long ago I would be able to have a conversation tonight.
Later I sat at the bar sipping a pink daiquiri through a straw. I just knew it wouldn’t be long until an unsuspecting dupe got the night of his life when the girl he picked up let him lead her into the bathroom for an ‘impromptu’ blowjob in a stall.
So, I was tricking guys, it wasn’t malicious.
I was so excited my hands trembled. I decided that my name for the night would be Treena.
Half an hour later the bar was half filled, disappointingly, no action yet. Scanning the room I saw a lot of couples but no singles so far. No groups of men either.
With my peripheral vision I saw the body of the woman ordering drinks next to me. She was tall and pleasantly plump, really long red flowing hair, with an ample set of breasts I could tell were real by the natural way they bounced under her jersey. She wore a feminine little ankle bracelet my mom would have disapproved of, saying only loose women wore them. But I thought it was cute with a little unicorn charm on it.
I leaned close to practice my whispering, the coincidence naturally led to me striking up a conversation: “I wore the same costume a few years ago.” I didn’t mention that mine included the secret underlayer. Noticing her ring I added, “I bet your husband loaned you his shirt?” She didn’t have a helmet, just eye-black under her eyes.
The bar was a little loud so she put her sexy lips right up next to my ear, “So we’re doing a whispering thing, I can play along.” She continued whispering, “I like your costume too. Very sensual! And yes It’s my husband’s. Not pro, but he played in his first year of college. I’m Alicia.”
A few minutes later her man, dressed as a cowboy, replete with hat and lasso, came over, wrapping his muscular arm around her intimately. We all hit it off and they offered to keep me company until I found a steady ‘dancing partner’. I kept my eyes on the room but apparently I’d picked the wrong bar since it seemed to be all couples.
I had a fantastic time with the friendly duo: Flint and Alicia. It almost made up for the fact that my night’s goal was a complete loss.
We took turns buying rounds and when Flint loosened up and started flirting with me as well as Alicia she didn’t even mind.
Another guy, dressed as the obligatory Dracula, flirted with me too, complimenting my “pussy costume” effusively, a bad play on words but I wasn’t here for humor or to start a relationship. But as luck would have it, soon enough, his girl, a female version of the same, swooped down on us putting a quick end to that.
I was feeling no pain when Flint dropped the bomb saying, “Treena…Alicia’s too shy but she and I have had this fantasy for a long time… She suggested I share it with you”
They waited to gauge my reaction. I flashed them my best smile, but then remembering that the soft mask hid my identity completely, I let my hand rest on Flint’s arm, “Tell me more.” Everything I said sounded more sultry while whispering.
Flint continued, “I’ve got this fantasy where my partner watches a hot woman service me. We’re sitting side by side on a couch while this girl is kneeling between my legs…and here’s where it gets interesting, then this girl moves over to my partner and does the same…back and forth.”
Alicia, tipsy as all get out, leaned close and whispered to me, with a drunken wink, I think it’s super hot and I wanna be a part of it.”
I looked back and forth between the handsome charming cowboy and the sexy footballer. I imagined myself between his strong legs, him thrusting his big cock between my lips… Then I imagined moving over to lick her sweet pussy… I haven’t even seen another woman’s pussy since I got married.
I glanced at her crotch. I could almost make out the form of her labia through the tight material of her jeans.
The idea of switching back and forth from one to the other was sooo hot. My next thought was that he would fill my mouth with cum, then I would fill her wet gash with cum straight from my mouth.
I agreed effusively, “You’ve found the right girl. That scenario totally hits my buttons. And giving oral is my favorite thing to do. I don’t even need anything in return.” I couldn’t believe my night was actually turning around. I couldn’t believe we were discussing what we intended to do. With the other guys things developed organically and without any planning. But here we were, Flint just said what he wanted then Alicia and I fell into line.
Flint put his arms around both our waists now. The touch of his nine inch bicep on my skin made me swoon. He practically cheered, “This calls for a celebratory shot!” Not only did he order us shots but he got us each a flight. He toasted to our night, “To my two favorite ladies!” Then referring to our costumes: “My beautiful furry kitty-cat and my gorgeous tight end. May we have a great adventure.”
For me the best part was knowing I had a secret – that only one of us was really a lady.
We drank up. In the conversation that followed I learned that they had driven in from the burbs and didn’t have a room. I volunteered my room of course – because it was right upstairs. I learned they had been together for three years. And I learned they were thinking of starting a family in a year or two.
Right after we saw the contest winners announced, we headed upstairs. We were all feeling no pain but still managed to stumble to my room. Outside the door I swiped my card then slipped in quickly to close the closet door so they wouldn’t see my male clothes hanging in there.
Flint looked around while Alicia tinkled, “This is gonna do fine. You’re a lovely lady, Treena. We’re so lucky we ran into you. Maybe after tonight we could make one of your fantasies come true.”
He put his hands on my waist, feeling up my body. I wasn’t worried, I had the best falsies I could afford, perfectly weighted, natural feeling nipples, everything but the jiggle. And my cock and balls were well hidden too. I answered, “You’re already doing that, like I said, I like to give.”
He spun me around then pushed me deeper into the room, “Aww, there’s no couch. I guess we’ll have to adapt.” He hugged me close groping my ass, first through the fur, then under. He even went so far as to let his longest finger touch my anus. He shouldn’t find anything as long as he didn’t reach too far. I let his tantalizing finger probe my ass while I rubbed his growing member through his chaps.
Alicia returned. She grabbed my buns too, so now four hands were squeezing and massaging my backside. She kissed my neck from behind then whispered salaciously in my ear, “I like a woman’s tush as much as a man’s. And your’s looks delicious.”
Together they lowered/pushed me so that I was on my hands and knees, laying over a footstool. Her language worried me a bit. Couldn’t have her poking around back there. I whispered back, “Alica, I’m here to serve you. It’s Flint’s fantasy.”
Flint wasted no time, his half hard dick was already protruding and rubbing against my lips. Meanwhile, Alicia had flipped my skirt up commenting on my tiger panties. I’m glad I opted not to wear any men’s things. But if she kept this up she would find something unexpected, and no doubt unwelcome, beneath my stripes.
As loudly as I could without breaking into a man’s voice I pleaded, “Alicia, bring your muff up here so I can switch between the two of you. You’re gonna love my tongue.”
Flint stuffed his cock in my mouth which unfortunately stifled me. He still wore his costume and, I suppose, on a lark, he wrapped his lasso around my head to better enjoy fucking my face. Perhaps I shouldn’t have told him earlier that I was curious about being treated roughly.
I struggled a bit. Not because I wanted to escape his hold on me but because I was powerless to influence Alicia’s wandering lips. She rubbed my whole ass through my panties and kissed the small of my back. I squeezed my legs tightly together hoping, against all odds, my package would be on the side away from her – but I could tell it wasn’t.
She started to slowly peel my underwear down, teasing me, rolling them as she went.
My thoughts were nearly totally consumed by what was happening on my front end. The last time I had sucked cocks I found it to be very important to control the depth using my hand as a stop. Today, I specifically wore gloves that left my hands bare. However, the way they had me splayed over the footstool I needed to use my hands to support myself and they were not free to protect my throat from the immediate stabbing danger.
The less pressing, but greater, danger was that of being discovered, and that was all playing out in the back. Alicia had my knickers rolled low enough so my asshole was exposed to her view. I sure hope it looked female enough, but just how did a female butthole look different from a male’s? It didn’t seem to matter to her as I promptly felt the flat of her tongue lapping at my previously most private part.
Flint had the ropes wrapped around his hands and was pulling on my head, thrusting in and out of my mouth with just a hint of force. He had a running commentary going the whole time, “Oh Babe, you have an amazing mouth. And the way you’re sucking me in with your lips is fantastic too You said all throats were equally good and we’re gonna test that. You ready? Did I mention how sexy your waist looks with your skirt hiked up and my partner’s face stuck in your ass?”
I sensed that he started talking to Alicia next, “You don’t mind the change in plans, do you? I really did want to get dual oral but there’s no couch. Let’s do an Eiffel Tower! That can be our surprise instead.”
Alicia lifted her face, “Oh Flint. You’re so wicked. Guess what? I’ve got a surprise for you too. I’ve been holding onto it all night.” Having said that she caressed my ass then stuck her hands into my panties stroking down my legs all the way to the back of my knees.
For a minute there it sounded like she knew I was a man. Restrained on the stool I wondered how much longer my secret would be safe? What would she do when she discovered it? I could struggle but I’m pretty sure I was going to be discovered one way or another – might as well enjoy it while I could. I hoped Flint filled me with his spermy flood first.
My internal struggles came to a sudden end when Flint decided to push into my throat. I was glad for the lasso, or his hands would be in my wig, possibly dislodging it. His cock fit tight in me. I’ve never had a cock actually go into my throat before and no one ever told me it would be tight. I was prepared for the possibility of gagging and had spent plenty of time practicing with Aimee’s dildo. Guess it must have been thinner than Flint.
Flint spoke enthusiastically, “Let’s fill her pussy up Dear! Doesn’t that sound hot?” I wondered if Alicia had a vibrator in her purse? Or if they planned to switch. I’d been looking forward to munching on her snatch ever since they mentioned it.
Flint kept working in and out of my throat. I would gasp for air whenever I could and he would remind himself out loud to let me breath. My body was rocking back and forth too, requiring me to brace myself against the footstool constantly.
Alicia drew her hands up the back of my thighs then let go of me. I’d dodged the bullet yet again. Next, I heard Alicia’s purse open, so that answered that question. With a click of the tube she squirted a blob of lube into my ass and smeared it in with her fingers. I felt her long nails, imagining the black polished points rubbing the lube into me.
She leaned over my back, kissed me on the back of my neck, and whispered, “We’re gonna share our surprise with Flint soon. He’s going to love it. Don’t worry Dear.” I knew exactly what she meant by ‘our surprise’ because her hands slipped down to grasp my balls just as she was telling me about it. So there it was, she knew!
This was the most exciting and thrilling part of the night. I delight in tricking unsuspecting men and now I had an accomplice! When he was done I would actually get to see the look on his face for a change, and he wouldn’t blame me because Alicia was in on it.
Flint seemed more concerned about the dildo. “Was it in your purse? Why don’t you go back there and fill her up. I’ve gotta know if pussy is everything you remember from your days of experimenting.”
Alicia got behind me and started pressing it against my anus. I’d never had anything up there before. I imagined a thin yellow vibrator like my wife’s favorite, but feared a thick purple one like my wife’s other vibrator. I wanted this super hot girl to take my anal cherry. Alicia’s body and Flint’s cock were going to be a part of my fantasies for a long time.
Flint continued to talk non-stop, “This is so fucking exciting! The two of us fucking the same girl. Did you finger her gash? Was she wet?”
Alicia pushed it in slowly but steadily. It took her several attempts: pushing in then retreating a bit only to resume entering my tight asshole. Once she had it all the way in she started with a steady rhythm. Flint went on fucking my mouth but asked, “Are you in? Is it in her puss?”
I loved the sensation of the large object up my bum.
Alicia answered, “Oh Baby, yes and no. And it’s great!”
” ‘Yes’ and ‘no’, whatya mean?”
“I mean, I’m fucking her and it feels great, but I’m not in her pussy.” She laughed, “I’m doing her ass.”
“Hot shit! I guess we’ve had more than one change of plans tonight. Should we tell her now?”
“Oh yea!”
Then to me Alicia said, “Treena, we’ve got a little surprise for you.”
And to Flint she said, “Flinty, we’ve got a little surprise for you too.”
Still sawing my mouth, Flint sounded amused, “Well out with it. We’re dying to know.”
Alicia practically sang her answer, “Treena here isn’t what she seems. She’s a beautiful, sexy – man. And that’s why I’m fucking her ass and not her cunt.”
Flint gasped!
She slapped my ass, talking to me now in a full throaty voice, “And I’m not what I seem to be either. I’m a man too! Flint’s my husband and I’m his.”
I didn’t know why I thought she had a dildo in me. They’d never said that. Of course, I realized instantly that Alicia was fucking me with a big cock. A big wonderful living penis. And it felt great!
I thought I was tricking them but it turns out Alicia had spotted my Adam’s Apple early on.
I did get to hear the shock in Flint’s voice when he discovered I was a guy. He thought he was fucking the mouth of a woman for his first time.
The two of them fucked me for a while more, eventually filling me with cum from both ends. They pulled me back and forth, four hands holding me tight. I tried to help, jutting my ass up and positioning my throat as straight as I could.
Flint kept talking, joined by Alicia’s deep grunts behind me. They had great teamwork, communicating and timing their thrusts. Eventually they came together pumping my mouth and ass with cum simultaneously.
We played together for a couple more hours. Getting naked and exploring what three guys can do together. We all came twice. All of their climaxes were in me.
We ended with the two of them licking my cock and sucking me off together. It was the best blowjob of my life.