Monica Turns Me Out

I guess I never really got over my ex, Monica. Her and I dated for a year and a half in university, and it was amazing. She looked incredible: 5'6, long brown hair, bright blue eyes, an hourglass figure with a perfect set of tits. She loved to get all dressed up with makeup, jewelry, tight clothes, and high heels -- that's actually how we met.

I was at a scummy student bar for a friend's birthday, getting steadily drunk off of cheap beer. She walked in and I'm pretty sure I immediately started to drool. She was wearing a pair of black leather pants, clear heels, a blue top with a deep V to show off her cleavage, and bright red lipstick (I've got a bit of a lipstick fetish, so this was my kryptonite). Luckily, I had enough liquid courage in me to go up and talk to this goddess of a woman, and by some miracle convinced her to take me home with her. I had more sex over the next 12 hours than I've had in some months of my adult life -- it was amazing. She was amazing in every position -- in the elevator up to her apartment, on the kitchen table, in the shower, on the floor, everywhere. She was hands down the best I'd ever been with, and by the time the sun was rising we both collapsed on the bed and promptly fell asleep.

I woke up to a blowjob, with her under the covers licking my quickly hardening cock. I came within minutes, and she swallowed all of it with a giggle. When she laid back down next to me and kissed me, I didn't even mind that she still tasted like my cum -- she was just so goddamn sexy. We started to talk, and it was only then that I discovered that the way she looked was the second sexiest thing about her. She had a wildly kinky mind, and her skills in bed came from experience. She'd been with 50 other partners (men and women), and all that experience had taught her exactly how to please. I couldn't believe my luck.

After talking for hours (mixed in with more sex, of course) we finally got up and I made her breakfast. I had to go to class later that afternoon, so we exchanged phone numbers and left. That was the beginning of our relationship.

Over the next year and a half, she introduced me to things sexually that I never thought I'd try. She'd toned it down during our first night together, but she was a domme. She loved telling me what to do, and the more resistant I was to the idea, the harder it made her cum when I finally agreed to do it. As with all things, it started small: going down on her after I'd already cum inside her. That soon graduated to kissing her when she still had my cum in her mouth, and eventually licking the cum from her fingers. Every time she made sure that my orgasms were mind blowing, and I knew she came hard, so I relented easily. All these things became a regular part of our sex life.

Then the kinkier asks started. She begged to finger my ass while she blew me. Once that started to become too 'regular', then she wanted to use a small vibrator instead of her fingers. The small vibrator became a larger one, then a full-on strap-on dildo. As a straight man, I would be horrified if any of my friends or family knew what she was doing to me regularly. At the same time, she made sure the sex was the best I'd ever had. I never wanted it to end.

One particularly memorable night was after both of us had a few too many drinks at a friend's party, and took a cab to her place together. After stumbling into the bedroom, we quickly stripped. She had a mischievous look in her eye as she pulled her pink strap-on dildo from her nightstand, and slowly put it on. Thinking I knew what she wanted, I turned around and started to bend over the bed for her before I heard "Wait! Put these on."

I turned around and saw she was holding the black lacy thong she was wearing earlier. I nearly jumped when she threw it at me, giggling the whole time. "Come on babe, it'll be fun! If you do it, I promise to hit that special spot inside you that you like so much."

I desperately wanted to please her, but this was a bit far. Wearing women's clothes? I'm straight, I could never do that. I started to object, but she stepped up behind me and began teasing my ass with one hand, while tweaking my nipples with the other. She knew how to push all my buttons, and I could tell she was using that to her advantage. A few long, languid kisses later and I was pulling the thong up my legs, feeling the soft lace against my body. I swear she took me to heaven that night: I'd never cum so much or so hard, and she made sure to let me know that this was going to be a new part of our sex life.

From that night until the end of the relationship, she made me wear panties whenever we had sex. Sometimes, she'd ask that I keep them on throughout the day as well -- on those days, her pussy would be soaked by the time we got somewhere semi-private to have sex. She loved knowing that I could be exposed as a guy who wears panties. She even started incorporating that into her dirty talk as she fucked me.

"You're such a fucking slut, I love it!" She'd say between thrusts of her dildo into my ass.

"I'm going to turn you into a perfect little femboy. You're gonna wear panties all the time, everyone's gonna know you're a sissy." The first time she said this, I actually moaned out loud at the idea.

"Ooohhh, does the little slut like that? Moan higher for me, girlier! I know you like my lipstick so much, maybe next time I'll make you wear it too!" The thought of wearing her lipstick was just so sexy for me.

"Someday, I'm gonna bring one of my gay friends home, you know...they're not interested in me, but they'd LOVE to get their hands on you. A little straight boy who's all ready to be turned gay? They'd turn you out into their little sissy in one night, easy." Fireworks exploded in my mind. That was a new turn on for me, and all I could do was moan like a whore while she fucked me.

"That's right babe. I'm turning you gay, and there's nothing you can do to stop it! You're gonna dress like a slut and get fucked in the ass by real cocks. You're gonna suck them off, and swallow their cum!" When she said that, I blew my load all over my chest and stomach. She slowed down and scooped up the cum, then fed it to me off her fingers. This new verbal humiliation just added to our crazy sex life, and she would reassure me every time that she was 'just playing around', and that I seemed to like it. The crazy thing was, I started to imagine it too. I don't know what scared me more: the fact that she liked it, or the fact that I was starting to warm to the idea.

All the while, school and life continued. I managed to secure an internship as a junior software engineer at a large company in the city. Meanwhile, she was accepted to a masters program at a prestigious university halfway across the country. We ignored the reality for as long as we could, but at the end of the year we couldn't put it off any longer: our relationship wasn't going to work as a long-distance one. We still had strong feelings and respect for each other, so we parted ways as friends. I thought that was the last time I'd see Monica.

Breaking up had been hard, and a pandemic shutting everything down shortly after I started my job certainly didn't help the loneliness. For the last almost two years, all I'd done was work, workout, eat, and sleep. I'd been good at my job and been promoted 3 times, but I still lived in the same little apartment I did during school. I'd even taken up cycling as a hobby to keep busy (and started to shave my legs as a result). I hadn't had sex in months either, so my nights were filled with fantasies of Monica doing depraved things to me. Sometimes she was alone, other times she brought a male friend. Every time ended with me inevitably blowing a huge load, then falling asleep shortly after.

That's why it was such a surprise to hear her voice. I'd just finished work for the week and was getting ready to hit the gym when I received a call from a number I didn't recognize. I answered, only to hear her voice.

"Hey! Long time no talk, how are you?"

"Monica? Holy shit, it's been too long. I'm good, how are you?!" I answered incredulously.

"I'm good! I'm actually back in town this weekend! A friend of mine from school wanted to see the little university town I couldn't stop raving about, so I promised to show her the sights."

"That's great!" I said. "I'd love to see you, if you've got the time!" I couldn't work out how I was going to get her alone with her friend in tow, but that wasn't going to stop me from trying.

"Actually, that's why I called! If you're not busy, we'd love to come over and have dinner if it's not too much trouble! I told her how good of a cook you are, so she's excited to meet you. I'll bring the wine, and we'll be there about 7. Sound good?"

I quickly check my watch. 5:45PM -- enough time to run out and get some ingredients, and throw something together. "7 is great. See you soon!"

The next hour and 15 minutes are a blur. I quickly cleaned, showered, ran to the grocery store, and threw together her favourite dish: handmade gnocchi. By the time I heard a knock at the door, it was almost ready. I barely got the door open before she leapt into my arms, kissing me on the cheek and neck and leaving lipstick stains. She looked as sexy as ever: this time in a little black dress and high heel boots. After holding her for a moment too long, I saw her friend and my eyes went wide. She could have been a clone of Monica, just with blonde hair. Monica grinned and turned to her. "This is Sarah! Sarah, don't be shy -- say hello!"

Sarah stepped in for a hug that lasted almost as long as Monica, kissing the other cheek and leaving even more lipstick. Thoroughly embarrassed, I helped them both with their suitcases and we all sat at the table to eat. As promised, Monica brought several bottles of wine and it wasn't long until we were all telling stories and laughing like old friends.

Deep into the night, after the dishes were cleared and we were all sitting on the couch, Monica looks at me. "So." She starts "I have a small confession to make." She started to grin, and put down her glass of wine.

"Uh oh. I know that look. What's going on Monica?"

"Well, Sarah here knows about you and I."

"What do you mean, that we dated?" I said, not really understanding. "Everyone knows that Monica, the pictures are still on Facebook."

"No, she knows about the things we did...sexually."

I start to immediately go red with embarrassment. I'd been getting steadily more turned on through the night, because she kept 'accidentally' showing off a little skin, or rubbing against me as she walked by. Now however, I was mortified.

"Don't worry! She can keep a secret. In fact, she was SO turned on by the whole thing. I told her all about how you used to dress up, how I used to use toys with you...all of it. In fact, she was so turned on that...well...she has a secret of her own to share."

I was too focused on what Monica was saying to notice that Sarah had stood up next to me. She had pulled her dress up slightly, and her thong down to her ankles. That's when I received the shock of my life: she was stroking her rapidly hardening 7-inch cock. Monica moved closer and began to whisper quietly into my ear as she left a trail of kisses down my neck. "I never forgot my promise...what I said I was going to do. The entire time we were together, I was conditioning you for this. I did the same to Sarah here. She used to have a boy name...and she was just like you. Doesn't she look pretty? Doesn't she look so sexy? Why don't you tell her she looks sexy?"

Her hand reached up my shirt and started to play with my nipple. As if in a horny trance, I say the words "You look so sexy, Sarah."

She started to squeeze and twist my nipple harder as she pushed me forward on the couch, getting behind me. She resumed her kissing and whispering "Doesn't her cock look so good? It's so hard for you. I've ridden her cock almost as many times as I rode yours, it feels amazing."

I can't help but notice that Sarah is stepping out of her thong and moving closer to the two of us. Her cock is eye level with me. Monica leans forward, and kisses the tip.

"Mmmmm she even tastes good! Why don't you just taste her? I know you remember what cum tastes like."

She gently guides my head forward, until my lips are right in front of her cock head. I can hear Monica behind me breathing heavily as she whispers the words. "Do it babe. Become a cocksucker. Suck that cock, I know you want to do it."

I look up and see Sarah breathing heavily too. She's obviously turned on by the whole thing, another thrall to Monica's erotic hypnosis. She starts to rub my cock underneath my pants and I'm already a slave to the pleasure. I open my mouth and take Sarah's cock into it, gently at first, then deeper and deeper into my mouth. I'm surprised how warm it is, and how good it tastes. I'd later realize that our entire relationship, Monica was conditioning me to love the taste of cum, and that I was already addicted.

I closed my eyes and I could feel someone's hands pushing me deeper. I can hear Monica coaching me through my first blowjob. "That's it babe...suck that cock. Use your tongue on the bottom of it, just like I used to do for you. You're a fucking natural, that's so sexy. Don't you dare stop until I say so!"

I feel her move from behind me, but I don't stop sucking. I open my eyes and look up to see Sarah, holding the back of my head gently, rocking her hips back and forth. She looks so sexy fucking my mouth, but I can feel the heterosexual part of me complaining that I'm not gay, I'm not a cocksucker. Still, when I hear Monica telling me to "Stop!" I'm reluctant as Sarah pulls her cock from my mouth, leaving a trail of drool and precum between her and my lips. I chase the cock with my mouth for a moment before I realize what I'm doing and I stop. Too late though -- both Monica and Sarah know I'm hooked, and that I'll do whatever they want.

Monica is standing next to Sarah when she says "Stand up and strip babe."

Sarah smiles at me as I comply. "We're going to turn you out, straight boy. You're gonna love dick by the end of the night, I promise." I shiver, not knowing whether it's because I'm scared or because I secretly hope she's right.

Monica helps me pull all my clothes off, until I'm standing completely naked. It's only then I realize in the brief moment she'd gone, she had retrieved her suitcase which was now open. Inside, I can see a few things: a dress, heels, and lipstick to match the two of theirs. A red wig. And vibrators, toys, and dildos of every size.

"Wow.. uhh...you guys came prepared?" I joked.

"They're for you, silly!" Monica said. She pulled out a black thong first, and as if by muscle memory I pull it on. "You know, those are the first ones you ever put on... they're for you now, babe."

Sarah cooed as she stroked my cock through the panties. The pleasure made my knees week, and we collapsed back on the couch as she started to kiss me. I could feel Monica sliding the high heels onto my feet, but didn't want to open my eyes. My heterosexual side was terrified at how good it felt to kiss Sarah, but was steadily getting quieter. Monica ran her hands up and down my shaved legs, and whispered "Good boi...that saves us an extra step."

Next came the dress, then the wig. At all times, one of them was touching me while the other put something new on me, ensuring I was too weak from the pleasure to resist. Sarah also made sure I had my hands or lips on her cock at all times. Monica made sure she never got close enough to cum, but she was dripping precum all over me before long.

They had me close my eyes for the makeup. I heard someone rummaging through the suitcase while the other applied eyeliner to me. I almost jumped when I felt a small, lubed vibrator slide into my asshole and turn on while they did it. The vibrator almost immediately found my weak spot, and I groaned with pleasure. That pleasure drowned out the momentary pain I felt as they pierced my ears and put on whorish hoop earrings. There was something so sexy about having pierced ears. Makeup could be washed off, clothes could be taken off. Piercings though - they were more permanent.

Once it was all done, they took me to the washroom and made me look in the mirror. Looking back at me was a definite slut: a redhead with red lipstick in a black dress and high heels. She had over the top makeup that screamed "Come fuck me!". Her earrings dangled from each ear, and on each earring was inscribed the word "WHORE".

I didn't have long to admire myself though. Sarah quickly flipped up the back of my dress (when did it become 'my' dress? I don't know), and began to rub even more lube on my asshole. Monica stood next to me and pushed my back down, bending me over the counter. She began to rub her pussy as she watched Sarah slowly push her cock into my ass, taking my anal virginity. As Sarah fucked me, Monica began to spout the dirtiest things I could ever think of.

"You're a slut forever now. There's no going back. No matter what you do for the rest of your life, you're going to know that there was a real live cock in your ass." I groaned as she reached down and started stroking my cock gently. Sarah started to push into my ass deeper.

"You're just like Sarah now. Sarah started off like you, now she's a slut. Doesn't she seem happy? Don't you wanna be happy like her?"

I could see Sarah smile in the mirror. She looked me in the eye "I'm SO much happier now. Monica turned me into a slut, and we get fucked together ALL the time! She told me about you and now you're going to be one of us!"

I tried to protest, but her cock hit that special spot inside me and it came out as a groan of pleasure instead. Monica leaned in again. "That's right slut, moan for us. Moan loud and as girly as you can! Nothing else is as good as having a cock in your ass, is it?"

I moaned again, but Monica grabbed my face and turned it to look at her. "No, higher slut! I want you to sound like a virgin woman getting fucked on her wedding day!"

Confused but so turned on by the situation, I complied. I made my voice high pitched, and moaned for them as loud as I could. Sarah rewarded me by sliding the rest of her cock into my ass, deeper than any toy had ever reached.

"You're a little sissy femboy aren't you? You love that cock, bounce your ass up against it! You're going to get dressed up with us and fuck cocks, aren't you? Men, women, trans, it doesn't matter to you -- you're just a hole for cocks now! This is just the start, you're going to get tits, lip injections, and a tramp stamp tattoo. This is going to be your life forever!"

My heterosexual side's resistance finally completely broke. I couldn't help it, the idea of being a permanent slut was just too sexy. "YES! I'm a sissy, fuck me!"

Sarah slowed down, before saying "Say it again! All of it!"

"I'M A FUCKING SISSY! A FEMBOY! FUCK ME HARDER!"

Monica leaned in. "Say you love cock more than pussy. Say that you're never going back to pussy, and you're going to find cocks to suck."

"I'M NEVER GOING BACK! I LOVE COCK MORE THAN PUSSY!"

Monica grabbed my cock and started to stroke. "Tell me you're gay. Tell me you're going to go on dates with boys, you're going to start dressing like this full time, and that you're just a desperate whore for cock. Then I'll let you cum."

Another fetish was just unlocked: the idea of going on a date with a man. I had a fleeting image in my mind of getting dolled up, taken in public, hanging off of some guy's arm as his arm candy. Then the image changed to him taking me home to fuck me like I used to fuck Monica. "FUCK PLEASE LET ME CUM."

Sarah slowed down again. "SAY IT WHORE!" she shouted.

"I'M GAY! I'M NOT STRAIGHT! FUCK ME, PLEASE! I'LL DO ANYTHING -- I'LL DRESS UP, I'LL DATE MEN, I'LL GET FUCKED ALL THE TIME! PLEASE!"