Brie's Night

My name is Brianne though often I go by Brie. It is not the name I was born with. I had it legally changed when I started my transition three years ago. That's when I began living full time as a woman. Since then I've had breast implants, adam's apple surgery and all the hair I didn't want lasered. I was happy matching how I felt. I still enjoy a sexual release of course but it's changed since the transition. It's a different group of people that accept the new me. The following is a recount of a time before I met Sandy, my partner for life.

I found a profile of a man living just a few miles from me who was looking. He has a fantasy of having sex with a transgender woman, one with a big cock. More specifically he wanted to be used by a woman with a big cock. We talked on the phone several times and exchanged many pictures. We agreed to go on a date to meet only. I wouldn't be going home with him that night. I called him an hour after I arrived home from our date.

"Hi Preston, it's Brie. Are you still interested in taking things further?"

"Yes. There's no doubt. I want to." he answered.

"There's one stipulation that I have. I will be reasonable, but you have to follow all instructions I give you without exception. Will you do that for me?"

"Yes, I will do anything you say to have a night with you Brie. I'm available any day that works for you."

"Saturday then. I will call you during the week to confirm." Knowing he's busy during the week I chose to make his first night as free from stress as possible.

Honestly what he wants perfectly matches my desires. I love the satisfaction of being the first time for someone being taken by a woman's cock. I always let them think I am the one doing them a favor. Thursday night I started the fun, calling to give him some instructions.

"Hello?" He answered.

"Hi Preston, I have a few things I want you to do before I see you Saturday. Tonight, shower and shave your body. Then use the body lotion you mentioned to keep your skin soft. Before you go to bed put in your small plug."

"Ok." He agreed.

"I want you to wear the small plug until lunch tomorrow. Then you need to switch to your medium plug." I instructed.

"But that means I have to take the other one to work and change in that bathroom."

"Yes, I know you can handle it. Wear the medium one until we meet on Saturday."

"Ok Brie, I will."

"Before I arrive clean yourself with an enema bag, then shower and shave and lotion your body again."

"Ok, I will Brie."

"Also... I'm Mistress Brie from now on."

"Yes Mistress Brie."

"Thank you, I will see you Saturday."

During previous conversations Preston had given plenty of hints about wanting to be submissive, some less subtle than others. I'm going to push him some because I know he will find it enjoyable. He also asked me to be sure his neighbors didn't notice me or see anything unusual. It is somewhat conflicted so I convinced him to let me arrive while it's light. In return I promised to wear a coat over my outfit, and I will.

Saturday arrived and I went to have a mani-pedi and lunch with my girlfriend Kylie, yes a girl like me. And yes she and I had fooled around before but decided to resist it going forward. We each really wanted something else from life. Over lunch and a few glasses of wine I told her what I had planned for the night. She wanted to do my hair and makeup. We took a cab back to my place and she started on me. I wanted my hair back so any of Greg's neighbors would see my striking makeup. She wove my long blonde hair into a beautiful French braid. Then she reapplied my makeup giving me a deep blush and dark smoky eyes with heavy black eyeliner and long fake lashes. The rouge lipstick she chose was perfectly lined and glossed to set everything off. My face looked striking and was complimented by my new dark red nails.

Kylie helped me into my outfit for the night. We started with black fishnet stockings with a black garter belt. I let Kylie pull the stockings on and attach them to the belt. Then she chose a dark red lace thong and bra. She pulled my thong on me and then clasped my bra. My cock was held to the side in my thong. It was soft and barely contained for now. She helped me into my stilleto boots that come just over my knees. They are perfect for tonight allowing my stockings to show. Last was the coat. I chose my lightweight dark red coat to complement Kylie's lingerie choices. It too is perfect for tonight because it barely covered my butt. It kept me legal but did nothing to hide my stockings and the garter straps.

Kylie and I had a few glasses of wine while getting ready so I called a cab. We checked myself out in a full length mirror just as the cab pulled up. We pulled an amazing transformation off. I looked incredibly sexy and slutty. Like sex on a stick. She gave me a quick kiss on the cheek so my makeup didn't smudge and I headed out to the car.

The cab driver was impressed. I had confirmed the address for her and she was still staring back. I had my knees together. While she was still watching I crossed my legs. I didn't reveal anything between my legs but it did let her see much of my left cheek. Enough for her to know I was either commando or in a thong. We made eye contact and she saw my smile as she was turning forward.

"Hot date tonight hon?" she asked as we pulled away.

"Yes, I'm meeting a friend." I replied.

"Sure looks like fun."

She and I had a nice conversation. She was truly interested in hearing more about the night so we set up a date for the following weekend. She dropped me off at Preston's house. I was sure to lean forward when paying to give her a full view at my bra under my coat.

I walked up to the door without caring who could see me or more importantly see my boots, fishnets and garter straps. Out the corner of one eye I see a neighbor turn and watch me walking. Hopefully they will ask Preston about it sometime. I rang the bell and waited. He opened the door and I walked in. Preston was concerned about me dressing like this when neighbors could see. He stopped talking completely when I took my coat off and told him to hang it up. He complied and I suggested he pour a couple of glasses of wine for us. I knew he had some all the time and i knew he needed to relax now. He handed a glass to me and drank from his.

I walked in a slow circle around him.

"Are you embarrassed having me here Preston?" I ran my hand across his ass.

"No of course not. I'm just not sure how to explain it to them. I haven't told anyone else about my desires."

"Your desires?" I asked so he would verbalize it again. It will be easier for him to accept the more he talks about it, even if it's only with me.

"Yes."

"Yes? Tell me what they are. Maybe I misunderstood."

"I want you Mistress Brie. I want you to take me"

"Take you? Where would I take you?" I teased him a bit.

"Mistress, I want to suck you. I want you to fuck me." His face turned a bit red from this even though we had talked about it many times on the phone and messages. I wanted his first cock to be the experience he compares all others to. I'll have to reinforce his desires.

"You're wearing too much. It's making me feel under-dressed. Strip for me." I instructed before walking over to his arm chair to sit and watch. He started unbuttoning his shirt.

"Be sexy when you strip for me Preston." He slowed and awkwardly spun around while I stifled my laugh. He dropped his shirt and started unbuttoning his pants. He swung his hips around and let his pants fall. He was wearing his black lace boyshort panties, nice choice. He pulled them off and turned to look at me. I smiled my approval.

He topped off our glasses and I had him sit on the couch. I walked to him and asked him what he thought of my outfit now.

"It's really sexy Brie. You're beautiful."

"Pull my thong off for me." He pulled it down and my half hard cock flopped forward. I held it up.

"Lick my balls Preston." He started licking them. His tongue was warm and was turning me on.

"Lick the tip of my cock." He complied by timidly touching his tongue to my cock head. "Lick it again. Run your tongue in a circle around the head for me." And he did.

"That's good Preston. Now put your lips around it and circle it with your tongue again." He did but hesitated.

"What's wrong Preston?"

"I just can't go back if I do this." He said.

"I know that's true. You already had it on your lips and tongue though. That won't ever change either. I know you need it. You've been needing this your whole life. Take it in your mouth slowly. You will feel better when you do."

And he did. He took in half stretching his jaw open to accommodate it.

"That's it. Take it in as far as you can. That's good Preston you have me really hard. Keep moving your head on me." He did. He took it in too far and gagged a couple of times. I slowed him down a bit and helped him with his technique.

"That's it, rub your tongue below the head. Now take it in all the way again cocksucker." He responded by taking me in his mouth half way.

"Take a deep breath and hold it while you swallow my cock." He took my eight inches in, down to my balls. "Mmm that's good. Now pull back and try it again my cocksucker." His nose pushed on my bare skin as my cock again slipped down his throat. I had him do it again.

"Do you like my cock in your throat?" I held his head on me.

"Mm hmm. " He confirmed as well as he could. I let him pull back before pulling his head down on my cock again.

"Are you my deep throating COCKsucker?" I asked emphasizing the cock. I wanted to be sure he accepts his newly found talent.

"Mmmmm." He confirmed.

"Good. Pull your head back and rub your tongue below my cock head, then deep throat me again Preston." He did. "Keep doing it."

"Hold my balls while you suck me. That's right cradle them. Massage them lightly. Good, that feels good."

"Mmmmm." He moaned adding a thrilling vibration on my cock.

"Oh yes, swallow my cock again then lick under the head." Preston did. "Oooh that's my spot, keep doing that to me. If you keep doing that you will make me cum. Do you want me to cum?"

"Mmm hmm." He confirmed.

"Do you want to taste my cum?"

"Mm hmmm." He confirmed again.

"Oh yeah you're making it happen. Ohh shit yeah keep doing that. Ohhhh I'm cumming Preston. Take it. Ohh Preston." I came across his tongue. Shot after shot I flooded his mouth. He swallowed it as it shot over his tongue.

I pulled him to me and brought his lips to mine. As we kissed I reached around and softly wiggled the plug in his ass. I tugged and pushed on it a few times making him moan. I broke our kiss and asked him to refill our glasses.

When he returned I suggested we head to his bedroom. I removed my bra letting my firm D cup breasts free, dropping it on his couch. He led us back and I laid on the bed.

"Please get me hard again." He kneeled over me and started working my cock with his mouth. After a few minutes I stood up.

"On all fours on the bed." I directed him. I grabbed lube and a permanent pen from my purse and kneeled behind him. I put some lube on the plug to start working it out. It was lubricated enough that I could spin it. I started pulling it and he moaned. I held his cock with one hand while pulling the plug out. He groaned at its widest point.

I lined my cock up to his hole. Me moaned when the tip touched him. I pushed and he moaned louder. I pushed harder and my head popped into his hole. He moaned louder still and started breathing heavier. I gave him a minute before sliding in another inch. He was stretching and tight around my cock. I slowly slid the rest of my cock into him. When I did he slid away from me and I had to pull him back. He was breathing heavily now so I waited again for him to adjust.

I pulled back keeping only the head of my cock in him. I saw a couple tears run from his eye when he turned his head to look at me. I slapped his ass hard when I slid my cock all the way back in. He moaned and continued breathing hard though he was a little looser around me. I repeated another stroke and slap. When I was filling him again I learned over him and kissed his back.

"Do you like my cock in you?" I asked him.

"Yes, oh fuck it's big. It's bigger than anything else I've had!"

"It's my ass now. I own it don't I?"

"Oh yes Brie, you own it! My ass is yours to use. Please ohhh."

I pushed my cock in completely again. He groaned loudly. It was still a lot for him to take. I pulled the cap off the pen and pulled back again. When I pushed in again I entered slowly and lightly dug a few fingernails into his lower back. I repeated this again. The third time I wrote my name in a beautifully feminine cursive across his lower back. I pulled my cock out to leave him feeling empty.

"Tell me again who's ass this is!" I slapped his right cheek hard leaving a pink handprint.

"It's your ass Mistress Brie! It's yours, you own it!" he yelled. I slapped his left cheek, hard.

"That's right, I own it! And I will fuck this ass whenever I want."

"Yes Mistress!" I slapped again, harder this time.

I pulled out and pushed in slowly again, drawing a flower to the right of my name. And again with a flower on the other side. I pumped him a few more times before I pulled my cock out.

"Lay on your back with your ass at the edge of the bed." I commanded. He obeyed.

I slipped my cock back into Preston's ass. I leaned forward over him to kiss. I love kissing him. His passion is intense. Our tongues played together while I pulled out and in a few more times. He was loosening a bit more.

I pulled his legs up to his chest while putting my knees on either side of his hips. He moaned and sucked my tongue. Knowing he could feel my boots and fishnets on his hips I started stroking his ass again with my cock. It was perfectly tight holding on to my cock. Each time I entered him he moaned and sucked my tongue. When I pulled out our tongues resumed wrestling.

After several minutes Preston started responding more to my thrusts. When I entered him he pushed back to meet me. I would pause with my cock fully inside him so he could grind his ass against me.

"Fuck me Brie! Your cock feels so big, ohh yes fuck me fuck me fuck me harder! Ohhhh"

And I did. I started pulling out slowly and ramming my cock in him. He kept telling me to fuck harder but it was nearly unintelligible as his moans and groans became louder. I fucked him harder. I slowed for a minute to feel his ass gripping me. I sped up. I needed to cum again.

"Fuck Preston you make me want to cum. Oh Preston do you want me to cum?"

"Yes please I want you to cum, ohhh."

"You have me close, your tight ass is really holding me tight."

"Please cum, I want it. Ohhhhh."

"Are you ready for my cum in you?" Building him up more.

"Ohh yes Brie. Cum in me! Uhhhhh, uuhhuh."

"Do you want me to cum in you? Do you want to feel my cock shooting off in you?"

"Ohhhhh, yes I want you to cum in me! I want you to shoot your cock in me! I want to feel you do it! I want to carry your load! Oh shit Brie I'm cumming! Ohhhh I'm cummmmmmming!"

"Oh yeah shoot your load on your stomach while I fuck you! Oh Preston I'm cumming too! Ohhh Preston keep cumming! Ohhh keep gripping my cock!"

When I looked down he squirted his cum covering his stomach and chest. I wiped a bit up with my finger and put it in my mouth. I sucked on it after I shot my cum in his ass. I leaned down to see beads of sweat on his face. I layed my chest on his smearing his cum between us. I licked some sweat from his forehead and then kissed him. I could faintly taste my cum from when he sucked me earlier. We made out for until my cock had softened and slipped from his ass. I broke our kiss and he smiled.

"I can feel your cum running from my ass."

"Oh shit you made me cum hard Preston."

I rolled off him. It was dark out his window. He went to the kitchen to refill our wine glasses. When he returned he laid next to me.

"Your cum was running down my leg when I got the wine. Makes me feel so satisfied. Thanks Mistress Brie, that was amazing."

"It was for me too." I said.

He turned on his side and I moved closer to spoon him. We slept. The next thing I know the sun is shining in his window and he is sleeping soundly in the same position. I wasn't planning sleeping over but it happened anyway. I saw the two glasses of wine on the nightstand so I took one and drank it. It went straight to my head. I started sipping from the other. He had mentioned in our conversations that he is a bit of a wine connoisseur. This one was excellent.

When the wine was finished I rolled back to him, spooning him again. I reached over to fondle his nipple. His breathing quickened and it got me hard instantly. I took the bottle of lube from his nightstand. I covered my cock with it and squirted the bottle between his ass cheeks. I put the lube back and resumed my place behind him. My cock slipped between his cheeks. I rubbed his nipple again. His breathing quickened again.

I couldn't wait for him to wake up. I slipped the head in him. He moaned and reached back. He pulled me to him and my cock pushed in completely. His ass was snug but looser than last night.

"Oh you feel good." I moaned. His ass enveloped my cock.

"Your cock feels so good in me. I need you to fuck me again." He said.

I started a slow rhythm fucking his ass. My cock slipped in his ass easily now. I reached further to rub his other nipple. I could feel his dried cum still on it from last night. I pinched it hard each time I slid my cock in. Preston was really getting into the rhythm. He met every thrust pushing back to me. We fucked like this for as long as he could handle it.

He started breathing really heavily and turned his head back to me. We held eye contact while I pumped his ass. I started to feel my orgasm rising and I warned him. He begged me to cum in him.

"Cum in me Mistress Brie, I need your cum in me. I need to feel it."

"Ohh your ass feels so good. You're making me cum. I can't hold it back. Ohhh I, I'm cumming!"

"Fuck me Mistress Brie, cum in me!"

Oh I came hard in his ass. My cock was throbbing and my body couldn't stop thrusting my cock in him. I held him close and rolled his nipple between my fingers. While my cock was still in him I put lube on my hand and reached down to his cock. It mixed with his precum. I rubbed his cock. He started fucking my hand. He came quickly in my hand.

We slept again until Preston's doorbell rang. He said a lawyer from his office needed some paperwork signed and would be back in a few minutes. I reminded him to wipe our cum off before answering the door. I slept through their meeting. When I awoke the only thing on my mind was using the bathroom.

Preston came back just as I was washing up. After handing my bra and thong to me he informed me that he had to go to the office. I got dressed and put on my coat. We got into his car. I let my coat open so he could see the shape of my cock through my thong. When he pulled up I leaned over to kiss him. Our tongues played for a minute. I sat back.

"May I see you again this Saturday?" He asked.

"I wrote my name on your back while I was in you last night." I said. "Have it tattooed this week with some flowers of your choice around it. I will come see it on Saturday."

"Yes Mistress, I will. Thank you."

We kissed again before I came inside. Kylie was waiting for me. She and I had a long detailed conversation about my night. Oh wow it was exciting to relive and Kylie got very hot throughout. That's a story for another time.