Brian's Story

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"Good boy," I felt my rim starting to spread as she pushed her synthetic cock inside very gently, "I'm going to go really slow and soft until you get used to it," she smiled, reassuring me.

"Yes, Emily," I moaned as another few inches pushed into my anus.

I felt so full and stretched open. It hurt, but I'm not one to complain. She was being gentle as she could. I focused on her face and how her perfect tits are upturned at the bottom and how hard her little nipples were against her brown areola.

"That's about half, you okay with that?" she asked as she slowly pumped in and out of me.

"Yes, I'm good, Mistress," I grunted.

"Good boy, I'm going to put the rest of my cock in you now," Emily said as she gently thrusted into me.

I groaned as she filled my anus completely and it made my toes curl. She settled with it entirely inside my ass. I was breathing really hard and felt sweat beads popping up on my forehead.

"You're doing great," she said softly with a grin.

Emily squeezed fresh lube into her hand as she grinded into me.

"How does it feel having my big cock in your ass?"

Her hand found my organ that was rock hard and grasped onto it. She smeared the lube along my short shaft.

"It feels so naughty, Mistress," I groaned as her fist began sliding up and down my slick cock.

"That's cause you are a naughty boy aren't you?"

Emily withdrew the silicone dick from my anus, just before popping out of my rim, and then it went back in. I grunted again. The fake cock had me stretched open, and as she pushed back in I felt it rub against my prostate.

"I'm your naughty little boy, Mistress. I love being your bitch," I mumbled.

Emily worked the dildo in and out of my ass, taking her time to pick up speed. Her hand on my tool pumped in time with her thrusts.

"Do you want me to fuck you harder?" she asked more sternly this time.

"Yes please, Mistress, fuck your bitch boy's ass harder," I moaned.

Emily put everything in her tiny body behind the thrusts, getting faster and faster until she was pounding into me. With every thrust, the cock would massage my prostate, making the sensations inside me go on overload. She had to let go of my cock and stop fucking me several times. Then she would pick back up like she had never stopped.

She was getting sweaty and strands of her mane stuck to her face. I loved seeing her breasts bounce on her chest with every thrust into me.

She played along as if she really did have a cock as she drilled me, saying things like, "Your ass is so tight on my dick," and "my cock feels so good inside you."

Every one of her nasty lines made my member throb and ache. My legs were starting to cramp from the curled up position I was in, but my girlfriend was fucking me in the ass with a strap on. I wasn't going to say something about it.

Emily really gave it to me, I don't know where all that power came from in her tiny body but she was fucking me harder than I had ever been able to do to her.

"Are you my anal slut, Brian?"

"Yes, I'm my Mistress' anal slut. You fuck me so good," I panted.

Her hand was a blur on my cock when she hissed at me, "cum now, Brian, cum on your slut face."

I exploded immediately. I hadn't cum all week per her wishes. The angle she had me in made my thick seed shoot onto my face. I closed my eyes tight after seeing the rope fly at me. I felt my hot cum splash onto my nose, mouth, and cheeks. I wondered how Emily was able to look up at me with her eyes open as she took my load on her face. That must have taken years of practice, I guess.

I felt Emily pull out of me and heard her working to get the harness off as I wiped my eyes, making sure it didn't hit there before I opened them. My cramped legs settled back down on the bed.

Emily hopped back on top of me and licked the cum off my face, sharing it with me between licks.

After I was cleaned up, she collapsed on top of me with her head on my chest. We both let our hearts slow down.

"That's hard work," she giggled, nuzzling her sweaty face into my chest hair.

"You were amazing," I smiled and dropped little kisses on her sweaty forehead.

Emily really is amazing. There has never been a woman I could be so open with or knew how to get into my head so easily.

The next morning while eating our breakfast of pancakes, eggs, and bacon, Emily brought up what we had talked about the night before.

"Brian, the cuckolding stuff that we talked about last night, was that just dirty talk or were you serious about it?" she asked, and then sipped her orange juice.

I had to finish chewing before speaking. "Well, it came up because of what was happening, but I was serious. I think it's something I want to try."

"You know how open I am and I could be interested in it, but I just don't want it to tear us apart. Do you know what I mean?"

"Yes, I do. I've never done it before, but it's something I've fantasized about for a while now. I can't guarantee I'll like it, but I would like to give it a try."

Emily nodded and then took another bite of her pancakes. I could tell she was thinking about it.

She took another sip of orange juice before speaking, "All I need is you, really. It kind of scares me to think about being with someone else."

I reached across the table and squeezed her hand. "Sweetheart, I love you. You're the best thing that I could ever ask for. Maybe we could give it a shot, and if we find that we don't like it or either one of us doesn't like it, then we don't have to do it again."

Emily rubbed the back of my hand with her thumb, "Okay, we will give it a try. But promise me that if you ever find that you don't like it anymore if it becomes a normal thing, let me know and we will stop immediately. No matter what."

I smiled. Her words made my heart melt.

"I promise you, Emily, if my feelings change about it I will tell you. And you'll do the same for me, right?"

"Absolutely. I don't ever want to lose you. I love you to bits," she said, and then leaned over and kissed my cheek with her sticky, syrup stained lips.

Of course we did explore some of her kinks as well; it wasn't just about me all the time. Emily is really into role-playing. She enjoyed dressing up like a cop, a sexy librarian, Tinkerbell, or my boss, to name just a few. She used a lot of her old Halloween costumes. Emily would act out the characters and tell me who she wanted me to be and it always resulted in fun, awesome sex.

Another fun thing we would do is meet at a hotel bar and make up fake names, pretending like we were strangers and sometimes cheating on our significant others. We would have a wild one night stand with each other.

Emily is also really into anal play. As I said before she had fingered my ass, but more importantly, she loved having hers fucked. The nastiest things would come out of her mouth when she was taking it. She also liked having her ass fingered while I gave her oral and even tonging her back hole. Butt plugs and anal beads were also common play toys.

She also enjoys some light spanking and has me take over a more dominant role from time to time.

There was still one big thing I was hiding from her though, and it was eating away at me. I was too embarrassed to admit it until she stumbled across it.

We also hadn't discussed her fucking other men since that morning. I kind of secretly hoped she had forgotten about it. I knew it was something I wanted to experience, but I was extremely nervous. She was busy with school at the time, winding down the semester and organizing the Holiday PTA performance, which I attended.

About a week before Christmas and right around our one year anniversary, Emily asked me to move in with her. Of course, I said yes. I hurried, packing all my stuff. It really wasn't that much except for my ridiculous collection of match box cars and comic books. I left a lot of that at my parents' house, considering the size of her apartment. I did bring along a select few favorites.

She helped me move my boxes on the first day she had off of work for winter break.

We were unpacking and the only big thing I brought with me was a dresser. I wasn't really paying attention to what she was unpacking because I was setting up my dorky display of cars on top of the dresser.

I looked down at her on the floor and immediately recognized the box of underwear and comfortable shirts I wore for sleeping.

"Emily, don't open that!" I panicked.

Her hands stopped moving, holding the flaps of the box open and she raised a brow at me, "Umm, why?"

"I just, I just want to do that one myself," I stuttered.

Emily looked down in the open box then back up at me, "What's wrong with it? It looks like boxers and old t-shirts."

"There's just some stuff in there, that's um... breakable." I'm a terrible liar.

My girlfriend looked ridiculously confused and shook the box, her eyes burned into me, "It's not heavy and it doesn't sound like something is bouncing around. Why don't you sit here with me and I'm going to pull the stuff out. You know we don't keep secrets."

I groaned in embarrassment and plopped down on the floor next to her.

Emily pulled out several pairs of boxers and t-shirts, folding them neatly and placing them on the floor.

Several agonizing minutes later, she found it.

Her hands pulled out a Ziploc bag stuffed with women's panties. She didn't say anything at first, taking her time, laying each pair out over her outstretched legs. There were about a dozen of them in the bag and she examined each one, making approving faces at the cute ones and sneering a little at ones she didn't like so much.

When she finished, I could feel the heat radiating from my blushing cheeks. They had to be bright red. I felt a little bit of sweat on the back of my neck.

"So, it looks like we have something to talk about," Emily said calmly.

"Yeah," was the only thing I could say.

"You don't just have these to look at do you?" she asked as her fingers ran over the neon yellow lace hipster panties on her thigh.

"No, Emily," I confessed.

"So, you like wearing women's panties?" Emily kept the same calm voice.

I gulped. "Yes."

My girlfriend's fingers moved to the next pair, a white cotton g-string with sort of leopard print on it with pink trim.

This fetish was also rooted back to the same night when I discovered how erotic feet were. I was curious and snooping around a bit in their bedroom after finding the magazines. I found the woman's lingerie drawer and, instead of just looking at them, I tried on a pair of black lace crotch-less panties. I looked at myself in the mirror with my penis hanging out. I felt naughty and taboo, in a good way. I felt like it wasn't a normal thing for guys to do until the wonderful internet showed me that it's more common than I thought.

I didn't steal her panties, but one day I was at a friend's apartment in college while she was doing laundry. She went to use the restroom and I swiped a little pink thong of hers out of the laundry basket and stuffed it into my pocket.

Another time in college I was at the laundry mat in my apartment complex. No one else was in there and I noticed a dryer full of women's clothes. I took another pair. I did this on more than one occasion.

I didn't buy a pair for myself until I was with my ex. While we were still having sex, I bought her a couple pieces of lingerie and a few pairs of panties for myself. Over time, my collection had grown into what was now sitting on Emily's legs.

I liked wearing them when I jerked off. I also enjoyed cumming into them and eating my cum off of the fabric. I also enjoyed wearing them under my clothes on random days when I was feeling naughty. I always kept my boxers on over them, not wanting obvious panty lines.

"You're such a naughty little boy, Brian," Emily teased me. "I wish you would have told me sooner. We could have been playing with this fetish of yours for months now." she grinned devilishly.

"I didn't tell you cause it's embarrassing," I said.

Emily nodded, "I understand, but you know how open I am about everything." Then, that familiar devilish grin returned to her lips that told me something deliciously wicked was about to come out of her mouth. "To make up for keeping this from me you're going to model every single pair, right now," she giggled.

"Seriously?" I gasped

"Yes, you naughty boy, right now."

Emily gathered all the panties and hopped up on to our bed.

She held out the neon yellow ones first, waving them in the air. "Let's get started."

I felt like my whole body was blushing as I undressed, and then took the panties from her. I pulled the little undergarment up my thighs and tucked my cock and balls inside the lace.

Emily started giggling hysterically, "It looks so cute with your little bulge inside," she could barely breathe she was laughing so hard.

I liked when she giggled at me, even in this exposed state. I'm a glutton for her teasing and embarrassment.

She was clapping her hands as I walked the "catwalk" in what was now our room, strutting back and forth in the area between the bed and dressers.

"Your butt looks mighty cute in those," she continued to giggle. "Now these." She waved a pair of black satin bikini panties in the air.

I took them from her and switched into those. This pair was a bit looser, and held my junk better.

Emily's unrestrained giggles continued. "I love it, you look so cute and girly." She reached out and snapped the waistband on me as I walked by.

"Are you just getting a kick out of this or do you like it?" I asked her as I put on the next pair, a green silk type material thong with light blue ruffled trim.

She cocked her head as she looked at them on me, "Actually I kinda do like it. I haven't thought about it before really, but I think we can have fun with this."

Her giggles erupted again as I walked the "catwalk" and she smacked my ass when I passed her. I still felt insanely embarrassed and on display but I was feeling more comfortable.

"Do you like how they feel on you or is it just a naughty type thing?" she asked as I put on the white leopard g-string.

"It's both, Emily."

The fashion show continued until we had gone through every single pair of my panties.

The next day, Emily and I went shopping. I thought I was in for another standard shopping trip for Emily to buy new clothes and lingerie. I loved doing that. I could also pick up the last minute Christmas presents I still needed.

However, as we were walking up to Victoria's Secret, she told me I would be buying panties for the both of us. I was shocked to be already buying panties for her and me. We picked out several pairs, two of each kind, an extra-large for me and a small for her. It was fine until we got to the cash register.

While the girl didn't say anything, I could see it in her eyes that she wondered why there would be duplicate pairs of different sizes. I felt clammy while Emily just smiled calmly. We got out of there quickly after paying and continued a routine shopping trip.

That night I fucked her with the baby pink silk thong I just bought. It was pulled to the side, exposing my cock. She had her matching pair pulled to the side, as well. It was Emily's idea, and it was very hot for both of us. That wasn't the last time we did that.

Over the next few weeks, she got really into our panty fetish. She deemed Friday as "Panty Friday" and I wore panties under my pants at work, without the boxers this time. Sometimes we would match. Other times, we didn't.

My collection grew exponentially. The first time she sent me out alone to buy panties for myself I was so nervous. I had done it before, but with her directions of what specifically to look for and being commanded to do so, made it different. Alas, I survived.

One night, Emily's friends Kate and Jennifer visited. Both of them were cute blondes, spunky and full of life. They had been her closest friends since college. We were having a couple of drinks and chatting.

Then, all of the sudden, Emily's hand rubbed my back and she said, "Brian likes wearing women's panties. He has some on right now."

She had exposed me. My cheeks flushed red and my heart sped up.

Her friends didn't believe it. They demanded to see them. Emily made me stand up with my back to them. She undid my belt and tugged my loose jeans down just enough so they could see the blue lace of my thong.

I heard them gasp and giggle. I felt like I should hate what was happening, but I didn't. I liked what Emily was doing to me. I always liked what Emily did to me or made me do.

Whenever we saw Kate and Jennifer after that night, no matter where we were, they would ask if I had panties on. If I did, Emily would make me show them and they would giggle just like they did the first time. I ate up every minute of it.

I guess I got off track there a bit with the panty talk. Emily and I did end up trying the cuckolding thing out about two months after it was first brought up.

The first time, we bit the bullet and put an ad online. We got a flood of responses. Emily looked so cute sitting on her laptop sorting through the disgusting and ridiculous e-mails.

We wanted someone normal-ish. When she would come across a guy whose picture and e-mail didn't seem too intimidating or freaky she would show it to me. If I agreed, she put it in the maybe pile. We finally had it narrowed down between two guys and met with both.

Emily and I couldn't decide between them. As long as all went well with the first guy, the other guy would be all set up for the next time.

Leading up to it I was quite nervous. I watched her get ready and put on a cute emerald green satin bra and panty set and a matching robe over her body. She reminded me that no matter what was about to happen, she loved me and I would be the one she went to sleep next to and woke up with in the morning. I got the hint she was a bit jittery as well.

After Emily let him in to our apartment his hands were all over her. Watching her kiss him was what got to me the most. We later agreed kissing was the only thing off limits. She didn't like kissing strangers and it hurt her as much as it did me. Fucking him wasn't even near as hard on my heart. She thoroughly enjoyed feeling his big cock inside of her and I adored seeing her face as she was filled.

Of course, we weren't stupid. He had a condom on, although it would have been fun to eat his cum from her body.

My cock was rock hard and she allowed me to rub myself through my pants. It was so hot looking in her eyes as he drilled her. She even told me she loved me while riding him.

Emily was gorgeous with another man's hands on her body and his dick that was almost twice the size of mine inside her.

I didn't think it was possible, but I loved her even more after that night. I made love to her used body after he left. We talked about what had happened. I woke up next to her the next morning, and still do.

This became a regular thing for us. Once or twice a month, we would post ads or call up a guy we had already used.

A few times, a close friend of ours would fuck her. Those experiences were always great because since he was our friend and we knew him well, he didn't have to use a condom. Emily threatened cutting his dick off is he gave her a disease. Yes, she is still clean and he still has his cock.

He would cum inside her pussy and Emily would make me eat the creampie from her. It was so divinely dirty sucking his cum out of her and then sharing it with Emily. Too bad we didn't have more friends we could have done it with, because we both really enjoyed that part.

Over time, she started making me be her bitch boy in front of the other men. I wore panties and she wouldn't allow me to touch myself while she was being fucked. Every time, it got more intense and we both enjoyed it more and more.