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My first encounter with Jake the delivery driver.
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Brian70
Brian70
171 Followers

I was enjoying a rare Saturday alone. It was a cool Fall day. My wife had to work until 4pm to meet with clients that were heading out of town in the evening. So I immediately started to do what I do when I have time alone. I dress, cross dress, become a sissy, whatever you want to call it. She had left early in the morning to do the final preparations leaving me with the whole day to be myself.

I wasted no time pulling off everything I was wearing and walking naked to the garage. I pulled out my breast forms and a green bra from the leaf blower box I keep on a back shelf. After putting them on I put on a matching green thong and garter belt with black fishnet stockings. I pulled my straight blonde bobbed wig from the same box putting it on. I also selected a pair of black Stilleto heels. I bent down to slip them on enjoying the sensation of the hair brushing my cheeks as I moved.

Standing in lingerie and heels brought the same rush as every time before. It never becomes routine, does it? The first time I stood in heels was amazing. Suddenly four inches taller, I felt the shoes pressing on my feet differently from what I was accustomed to, having to catch myself from losing my balance by putting my hand on the door jamb. At first I thought I would never take them off. Now I still get the rush of excitement even though I have learned I will appreciate taking them off after several hours.

I stood with confidence in the garage. My feet firmly planted at shoulder width and my hands on my hips. My reflection in the car window brought a smile to my face. Well more of a satisfied smirk. The curve of the window distorted the reflection while the tint made it clear. It showed the reflection of a sexy blonde in heels and lingerie. A few times I had gone for a spin daring people to see me. When the weather was nice I always put the windows down. The weather was not nice and car was low on gas so I decided today wasn't going to be one of those days. And it was too chilly to stay out here. Even the house was going to require some clothes for warmth. I walked back inside heading to my closet. I enjoyed the sound of my heels clicking as I crossed the concrete and then tile floor as I stepped inside.

Once back in the closet I checked my appearance in the mirror. With approval I moved on to shave the stubble on my face, temporarily taking my wig off to keep it dry. I had shaved everywhere yesterday so a quick once over here would do.

I pulled a pleated charcoal knee length skirt from behind my dress shirts and a snug white sweater from the back of a drawer of sweatshirts. Pulling them on I checked my look in the full length mirror again. It all came together well except the natural look of my face. I put on lipstick, eyeliner and a little eye shadow. Just enough to make me happy but would be quick enough to remove. It had been a while since the last time I had this opportunity and I wanted to use every second.

I opened a new bottle of merlot, spent the day with a couple of romantic comedies and called some friends and family members. Yes, a couple of them commented that I was cheery. I sounded happier than my usual self. I really wished I could tell them that Brianne was happy to be out. I managed to run and unload the dishwasher and even washed a couple loads of clothes. Domestic chores gave me the excuse to walk around with a casual purpose. Every step satisfied my needed feminine feeling with the skirt hitting my knees, the sweater accentuating my temporarily endowed chest and the heels forcing a sauntered walk, clicking when I crossed the tile floors. Every step also built the need to feel it more though. One day I would have a significant life change but it wasn't in the cards for today.

All too soon my alarm went off reminding me to change back to pretending to be a happy male. I cleared it from my phone grateful that it gave me time to change yet frustrated and disappointed that Brianne's time was up.

I had about forty-five minutes to do some last minute chores and clean up before she would be home. Time to man up I guess, literally. I laughed to myself at the idiocy of me being manly. I fake it well enough but long for the day where I don't have to.

I took the last remaining sip of merlot from my glass and stood to go change. Wow. I was a lot drunker than I expected. A lot. I walked to the kitchen to see I how much of the bottle of wine remained. Empty, I guess that explained it. I put it in the recycling container we keep by the counter then took it all outside to the bin in our side yard by the gate. I had enough experience with heels that I could manage getting around carefully while drunk. Frankly today I didn't care if the neighbors in their two story homes happened to look out and see me. Ok, I probably did care but the odds were low.

Done and back inside I headed upstairs to change.

DING DONG.

The doorbell. I am not answering dressed like this. Plus I was already upstairs. We often have the same man bringing packages so I couldn't out myself.

DING DONG.

Then I froze. My heart raced as I remembered. Fuck, she mentioned I would have to sign for a delivery today that she needed. She couldn't wait until Monday for it. Fuck, what can I do. If I didn't get it she would check and see him come and go on our surveillance. She'd know I didn't answer it. The system she wanted installed. I had to get it. I had to open the door.

I went to the door hearing the doorbell ring a third time.

"Coming!" I called out on my way.

"Hi." I said opening the door just enough for him to slip the envelope and device through to sign. I just got the device though.

"Hey, I've got three boxes. They're heavy." he said. I recognized his voice. That voice. That sexy voice, his voice always made my heart skip. It was Jake. He was usually here a couple times a week delivering to us. We occasionally had conversations when he stopped. He was a few years older than me and very attractive. I had tried to check him out with every opportunity. He looked like he was in good shape and my eyes were always drawn to his crotch. There was always a generous bulge. A couple of times I thought I saw the shape of a nice cock hanging down his pants leg.

"You can leave them there. I'll get them shortly."

"The rain is just starting and they'll be soaked in just a few minutes. They're still on the hand truck so I can bring them inside easy."

"Ok, give me a minute or two here to get something on." I responded. Maybe he'll believe I was just showering if I mention it next.

"It's a deluge out here, I'll be quick and not look. It's alright."

Defeated. I had no choice. I knew there was no way he wouldn't see me. Even in just a peripheral glance my skirt and wig would be obvious. I decided that I had to allow it.

"Ok, come in." I let him in. He brought the boxes in setting them to the side. And I thought to myself, you might as well look, you couldn't miss seeing me anyway.

At first he didn't look because I was partially hidden by the door. It wouldn't last though. When he turned to leave he froze. I felt the cold air rush in, rushing past my calves. It fluffed my skirt giving me another feminine sensation. My mind flashed to being a woman walking on a sidewalk downtown before returning to the present reality of my life as I know it crashing down.

It seemed an eternity before he spoke. I felt my breathing quicken.

"Uh, you're in makeup and heels and everything." he said. Was he offended?

"Uh huh." I acknowledged blushing hard.

"Really. Hah. So uh what's going on? Are you alone? Does wifey know about this?" he chuckled again after his question. Well, at least he didn't seem offended. I didn't think he was.

"Alone." My face had to be bright red by now. I could feel it burning. Every millisecond I waited for him seemed an eternity. My heart thumped so loud I thought I wouldn't hear him if he spoke. I thought I was going to pass out.

"Well, you don't look too bad. Pretty good for a sissy actually." Jake said.

"She'll be home in thirty minutes. Sorry, I'm really embarrassed. Please don't mention it to her when you see her." I responded without registering what he had just said. Wait, did he say I look pretty good? The wine must have made me hear what I wanted. Sissy? True but what did he know about that?

"Mmm. Well, I could but I don't know. It might come up just in our normal conversation you know. Your house is on my route pretty often. I can't promise it won't come up." he said.

"Please, I, look she doesn't really need to know this. What do you want? I-"

"Well, maybe it's not my business to share. If I'm keeping your secret maybe you could help me out a bit."

"Ok, sure. Anything. What do you need?" I responded without thinking. Besides I had no choice but to comply with whatever Jake asked. At least I had a way out.

He stood waiting. I was oblivious to what he was really asking for. He closed the door and walked to the living room. I followed at that point figuring out what he wanted. He turned and stood, waiting again. I kneeled on the carpet feeling my stockings only partially blocking the scratchy fibers pressing on my knees. I reached out to his belt, unfastened it and unbuttoned his pants. They fell a few inches and I pulled them the rest of the way down. I pulled his boxers down next revealing a gorgeous eight inch cock.

"Fuck, you're big." I said without really consciously realizing it. It was beautiful. I stared at it while I pulled off his shoes and he stepped out of his clothes.

Wearing just the button down shirt he walked across the room and sat on the couch. I crawled across watching him watching me. I placed my hands on his knees spreading his legs. I kissed his knee. I moved up his leg kissing his soft and lightly hairy skin. My blonde hair brushed over his dark hair turning me on to no end. I lifted his balls to kiss where they rested, then kissed them. I kissed over to the base of his cock. My tongue came out and I licked up to the head. His skin was sweaty and a little salty from the day working.

I circled my tongue around the head before taking his cock in. I took it in until my lips were wrapped around the base. I had taken a breath and was holding it while his swollen cock head was in my throat. I felt his balls press on my smooth chin. I looked up at him as I pulled back.

Fuck, he was pointing his phone at me. I went to pull off the rest of the way and take the phone. This blow job was over!

He used his other hand to slam my head back on him blocking my airway again. My eyes watered as I stared at his eyes. They were not looking at me. I couldn't push myself up. He wasn't using much force though because I had submitted. I tried repeatedly to make my hands move and my arms to push to no avail. I wanted that cock in my mouth.

Several seconds later he looked at me.

"That video is synced to my cloud account." he started. "It's just some insurance."

I nodded my confirmation feeling a rush of embarrassment and anger, and then adrenaline shoot through me. The doubt I felt about wanting to go further didn't matter any more. Fuck, he owned me.

My eyes watered from his cock still held in my throat. I was nearly out of oxygen. He let go and I pulled back coughing and trying to catch my breath. I closed my eyes and saw a few flashes from the camera. Then I stared at the camera. Fuck it, it's too late now.

He touched the screen and then scanned the camera around the room. Then it was pointed back at me. I smiled making eye contact with the camera lens while I went back to sucking his cock.

"Tell me your name." he said.

"Brianne." I said pulling off just enough to say it. I kept eye contact with him.

"Brianne, what's your number?"

I told him.

"You like dick?" he asked.

"Yes." I responded exhaling as I answered. I felt like I was admitting it to the world.

"You like my dick?" he asked.

"Yes. It's beautiful. I love it in my mouth and throat." I said.

"Are you going to worship my dick?"

"Yes sir." I responded.

"Are you going to suck my dick again when I feel like it?"

"Yes, I want to suck it every day." I responded again.

"Good. You want it in your ass don't you?"

"Yes sir."

"You want my cum too?"

"Yes sir."

"You want it on your face?"

"Yes sir."

"You want it in your mouth?"

"Yes sir."

"Are you ready for it in your ass?" he asked again.

"Yes sir. Please." He pulled me off and up.

"Get some lube." he said.

I stood and rushed to the bedroom. My heels clicked through the tile hallway. I returned quickly handing it to him. I was starting to get worried about time. I probably had fifteen minutes left. He put some lube on his cock and handed it back. I lifted my skirt and pulled my thong to the side before squirting some in my hole. I rubbed it around as much as I could.

He pulled me to him. I straddled his legs. My legs naturally parted as I lowered onto his thighs. I reached down to his cock. I aligned it with my entrance and eased down the rest of the way on him. I felt my entrance stretching around the head as it parted me. Fuck he was thick. When I got the head in I started to ease the rest of the way down. He held the camera to capture us from the side.

I was quickly taken over by his cock. I forgot about the camera. I forgot about the time. I knew I had to go change and remove my makeup but I couldn't. I started riding his cock slowly feeling every detail as it slipped in and out. I put my hands on his chest and proceeded to stroke his cock with my ass. I started sweating as we fucked. I quickly realized this was so good I didn't care who knew. If my wife had walked in I wouldn't have been able to stop. She would meet Brianne. Slutty Brianne. Slutty, needy, feminine Brianne.

I heard a notification from my phone in the other room. Probably my wife saying she was almost home. Oh well, she was going to get a show. This was worth it. I rode him faster and he kept up, moving in coordination with me. He was enjoying it but he didn't seem anywhere near coming.

He moved his hand momentarily so I could see the time. Fuck, it was exactly when I expected my wife to be home. I started to panic more and almost thought of pulling off of him. My legs were starting to give out as he started moaning. They increased as the burning in my legs did.

"Oh fuck, ready for my cum?" he asked.

"Ohhh, yeah baby. Give it to me." I responded.

"Oh fuck you have me close. Ohhh!" I stared into his eyes as I kept riding him. I saw it on his face just before he was about to explode. He lifted me off him.

"Kneel and get ready for it." He ordered.

I knelt and looked up to see him holding the phone recording us. I opened my mouth obediently while looking into his eyes. I watched his face change as his orgasm started. He jerked his cock a few times before unleashing the torrent of hot cum. The first shot blasted across my face from my hair to my chin. The second covered my cheek forcing me to close one eye. It seemed like it would never stop as shot after shot landed on my face and sweater. When it finally slowed I licked the head, milking him to get the last few drops.

"Thanks Brianne. That was hot." he said as soon as he finished. He ended the video recording on his phone but took a few closeups of my cum covered face. I didn't care. I was so turned on that I just wanted him to fuck me again soon. He put his underwear and pants back on and I went out to watch him walk out to his van.

Just then I saw her car coming up the street. I slammed the door and ran in my heels upstairs to the bedroom. I pulled my sweater, skirt and heels off throwing them in my hamper. I pulled my breast forms out hiding them in the sweater. I set my wig softly inside the hamper too, on top of the clothes. I heard the garage door close as I moved to the sink. I used a towel to wipe as much cum from my face as possible. I rolled the towel to conceal as much cum as possible then put it in the cabinet under the sink. I pulled out a cleaning pad to wipe off the remaining makeup, quickly throwing it in her trash to be camouflaged with the others. I pulled on sweat pants, a sweat shirt and socks over my lingerie then walked out of the closet. It was just in time to pass her as she went to change clothes.

"Hey, I saw the boxes in the hall. Thanks for signing and bringing them in." she said.

"No problem. Jake actually brought them in."

I couldn't believe how close it was. Later that night Jake texted me a link to the private site with the videos and pictures. I was able to watch and relive it. It was so hot to watch him fuck me. I'm sure I watched it several times that night. This was just the first time that Jake had his way with me. There were many more times that I dressed for him. Sometimes he made me meet him somewhere. Each time we met he recorded it.

Brian70
Brian70
171 Followers
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3 Comments
ptscuriousptscuriousabout 2 years ago

Personally if I called at a house and found a Woman such as Brianne, I would want to Suck her Cock, because I am a Cock Sucker myself, not Sub or Sissy just a perfectly normal Man who loves to Suck Cock and if the Cock to be Sucked Cums Dressed in Sexy Feminine attire all the better.

TurningintoCDTurningintoCDalmost 6 years ago
Amazing!

Awesome story! Please continue! I want to read more chapters with these 2 characters. I would love to be Brienne

AnonymousAnonymousalmost 6 years ago
A friend in need

Why the need to record his pleasure delivery. With the secret out he can enjoy life so much more. The threat of blackmail is not needed.

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