Rebecca's Ch. 11

Story Info
Business trip with Craig to the city of Big Apple.
3.7k words
4.69
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9

Part 11 of the 11 part series

Updated 06/10/2023
Created 08/14/2021
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It's been a few months since I moved in with Rebecca and Craig. During that time, I embraced my feminine side, completely resigning from any male aspects of my life. I was living a hundred percent en-femme and I was incredibly happy about it.

Years before all that situation, when I watched porn on the Internet, I was repelled every time when there was a close-up scene on the penis of a male actor. I'm not talking about some lesbian scenes, where any kind of toys, including strap-ons, were in play. I am talking about real penises. And there were a lot of scenes, where the camera was pointed more on a dick during penetration or even male orgasms, and I was sick about it. I had to immediately fast forward it, to look at some hot, big-boobed blonde wearing lingerie. I am saying this because I never knew how much pleasure is given by a male penis, and I am still surprised that I have fallen in love with sex with a well-endowed man. Before, disgusted and repelled by the thought of even touching another man's penis, now - I cannot imagine not holding it in my mouth and giving sensual twirls with my tongue on its glans.

Another part was semen. I came so many times when mentioned hot blonde received torrents of sperm on her face, but I never thought about myself in that position. Today I'm trembling in ecstasy, when warm, thick cum lands on my face, gluing my dark-painted eyelids and extended eyelashes. And the taste! I feel fantastic when Craig is filling up my mouth. It's the ultimate reward for me and a sign that I made him happy.

The last thing that I want to mention is anal sex. Even the day before meeting Rebecca I enjoyed watching it, especially how the girl's ass is filled up by some big cock. The thing is, I never even imagined myself putting even a finger up my hole. It was a one-way road, and I wanted to keep it that way, but Rebecca showed me a whole new dimension of pleasure through anal stimulation. Sure - plugs and dildos are great, but they cannot replace a real human being behind me, thrusting a dildo, or even better - a real penis inside. Chastity was a great help here. I would never decide to put anything in my butt if not the chastity. It controlled my male, if it even is called like that, erections and what's more important in my case - significantly worse orgasms in the best way possible, forcing me to check the new things. Of course, there is a problem with hygiene down there, but when it becomes a routine, it's no problem at all.

So I am living as a woman, being a lady on daily basis, but acting like a whore in bed. And I love this lifestyle, but I wasn't ready for the things that happened recently.

I was sleeping with Craig that night, wearing nothing more than black lace panties and babydoll. My red painted toenails were showing up just at the edge of the blanket I was sleeping under. When I opened my eyes, Craig kissed me on the lips, and slowly guided my hand on his already swollen member. I love to tickle him down there with my long nails, giving him a little pleasure, but I knew exactly what he wanted. What I wanted as well. A moment later, my head was bobbing under the blanket, swallowing his rod as deep as I could. Deepthroat wasn't an option here, because he was too big, and even after intensive training, I couldn't do it. Still - I was enjoying having his warm meat in my mouth.

Morning blowjobs became something very normal when I slept with him. He loved when I swallowed his load to start my day. And I was proud that I could start the day in this way. Maybe it will sound disgusting, but I never brushed my teeth after that, but the moment after I ate breakfast. I was thinking about this conditioning, just when Craig filled my mouth with his sticky semen.

"Did you like it, baby?" Craig asked.

"As always," I responded, running my tongue through my teeth.

"I'm so happy you like to do it. It may sound dirty, but you are the perfect cock sucker!" He laughed.

"If it comes to sucking your cock Craig, it sounds like a compliment! Although every time when I sleep with you, the first thing I want to do just when I open my eyes, is to put your dick into my mouth."

"That's sweet honey, but don't you have the same with Rebecca?"

"Unfortunately not. Don't get me wrong - I love to eat her out, but there is a need for a romantic atmosphere. In our case, we just go straight to business."

"Does that make you unhappy? Because we can be romantic -"

"No, that's the point! I just love to suck your cock, not making a big deal about it, and go for breakfast."

"To be honest, I like it that way as well. Of course, we can be romantic later, right?"

"Yes, definitely, I love to have romantic sex with you too."

"Whew! I thought you don't like it when I'm kissing your neck when we are in doggy position."

We both laughed, and we went to the kitchen to eat something in the morning. Rebecca already left, but I saw two pieces of luggage - one black and one light purple.

"What's this Craig?" I asked.

"Oh, that's the surprise. You and I are going to New York for a week. I have a court case there, and we talked with Rebecca about that would be a huge step for you to travel through states as a woman."

"Wow... That is a really big step. What's in the baggage?

"Clothes packed by Rebecca. For you, of course, I've packed mine. She said you will love it. We have a flight soon, so let's eat breakfast, go dress casual and we will go to the airport."

We both ate light food, and I went to my wardrobe. It was a rainy, cold day, so with my light pink lace bra and panties, I decided to put on more opaque stockings to warm my legs. They needed a garter belt, and the only one which could hold them had metal clasps. I've put it on, and picked a black skirt just above my knee and knee-length leather boots with red soles. With my top, I went for a cotton, turtleneck blouse in burgundy, covering it with a black leather jacket, matching my shoes. Soon after that, we drove to the airport.

When we were already standing in the queue to check in, I saw a security checkpoint, with a metal detector gate. And I've panicked. Metal clasps? Checked. Metal bra joints? Checked. Metal chastity? Hell-checked. Fortunately, Craig quickly noticed what was going wrong and calmed me down.

"Diana, it's cool. They will check you on this gate, but even if you will have personal control, it will be done by a woman in a private room."

"That doesn't help at all" I was almost crying.

"Calm down, everything will be all right."

Soon, our turn has come, and when I was crossing the gate, there was loud beeping. I felt like a criminal when they moved me to the side, and a chubby guard scanned me with a hand metal detector. There were beeps as well, and I was told to move to room number three for personal inspection.

A nice dark-haired woman in her late twenties appeared at the door, wearing a security uniform and latex gloves.

"Hi, please take off your clothes to the underwear."

I did as instructed and stood in front of her just in my lingerie.

"What is this small object in your panties ma'am? May I please ask you to take it out?"

I was sweating like a beaver in the water.

"Un- Unfor... I'm sorry. Unfortunately, it's impossible."

"Okaay, then I need to ask you to remove the panties. Sorry ma'am, but that's the security policy."

Embarrassed, I slid them down, revealing my metal chastity cage.

"It's... It's some kind of tube on your... Penis?" She asked with visible shock on her face.

"Y-yes. It is."

"Why you didn't say so before? I strongly accept this kind of lifestyle and you have to know that I support you in hundred percent. You are traveling with this handsome man you standing next to?"

"Yes, I do."

"Nice! I see you are traveling on business, so I cannot stop you more. I wish we could have more time to talk about this." She pointed at my cage. "You are good to go - ma'am" She winked, and told me to dress up and leave the room.

When I went back to Craig, I told him about the whole situation. "I told you Diana that everything will be all right. Women understand these things. Now let's go to the plane."

The flight was usual, and we landed in the city of Big Apple. The cab drove us to our apartment, which was on the top floor of one of the best hotels in town. We even had the balcony with a glass railing, and the view was... Well, I thought that seeing Central Park in the sunset for the first time in my life will stick in my head till the end of my life, but the next thing that happened was even better.

I was standing there, bending over the railing and admiring the view, when Craig came to me very close and started kissing me on the neck. I moaned silently, but I felt his stiff cock rubbing against my skirt. In no time, he slid it down, moved my panties to the side, lubed my ass with saliva, and slowly pushed his enormously hard penis inside. And at this moment, my moan wasn't silent anymore. I was penetrated by his massive cock, standing on a balcony and having a whole New York in my sight. I just hoped that the glass barrier won't break and we won't fall down, but with every thrust of his shaft, I felt my orgasm is closer and closer. After a few more thrusts, my eyes widened, my mouth shaped in a big 'O' and I came.

My climax was silent. Not a single sound came out of my mouth, but I felt massive pleasure throughout my whole body. My juices were going through the pink lace fabric of my panties, landing directly on the balcony. I just looked down for a split second, but I never produced that amount of white sperm in my life. And the better thing is - it didn't stop, as Craig continued his vigorous penetration of my stretched ass hole. His tempo was getting faster, as he finally grunted, and the only thing I started to feel was his pulsating member, filling up my ass with his warm and sticky seed. Maybe a minute later he pulled out, and a tremendous stream of semen ran out of my ass. He bent over and kissed me on my neck again.

"That was incredible Diana." He whispered into my ear. "Would you like to take a shower with me?"

"Yes, I would love to. And yes, it was amazing. I don't know if I ever came so hard."

"But you were so silent, honey."

"I know, but the feeling... I thought I'm going to black out."

He laughed. "That's cute. It means that the fuck was good, right?"

"Right." I laughed too.

Craig after our short after-talk went to the bathroom, and I started to get myself together to join him. My stockings were ruined, at least the tops of them, all of Craig's cum flew out of me and soaked into them. Panties? There were more both of our juices than the lace fabric itself. They were incredibly sticky, but I was surprised how much of these juices were mine. I followed Craig, undressed from my sticky clothes, and put them in the sink, to handwash them later.

The shower cabin was big enough, so the two of us could easily get inside. Craig took a bar of soap and started covering my whole body in it. He even played with chastity on my locked penis, but I didn't feel much pleasure from it, and suddenly it clicked and I was chastity-free.

"What are you doing Craig?" I gently asked.

"I want this thing off for now." He said. "Look how small you've become." He put his pointing finger on my completely limp dick. "Does it frighten you?"

"No, what it would frighten me?"

"You know you will never use this for sex again, right?"

"I am very aware of that. Besides, why would I want to use this, if I have this?" And I grabbed his semi-erect cock.

"Whoah! I didn't expect that! But don't you think sometimes of fucking Rebecca with your real dick?"

"No, I mean... I feel much better when I put on a strap-on and we can have long-lasting lovemaking? It's like 'I can have whatever dick I want, and give pleasure with it'. And when I want to cum, and of course when Rebecca wants me to cum, she uses the strap-on on me."

"So.. you like to be fucked?"

"Duh!" And we both laughed.

We finished the shower, later than sooner to be honest. I was hypnotized by soaping and cleaning Craig's cock for a few minutes. I think he liked that, and I was admiring the view, caressing the full length of it with my palm. Craig returned the favor, cleaning my bottom and my shrank penis as well. We finally went out of the shower and dried each other bodies. I opened the suitcase to grab something to wear, and I was stunned. On the top of the clothes was a note from Rebecca.

"I've packed more "erotic" clothes for you, Diana. I hope you will both enjoy them. xoxo, Rebecca"

The first thing just below the note were black panties. Full lace, but with small writing on the back. 'Hard cock here please' With pointing directly to my hole. When I slid them on, the writing became a little big bigger, due to the stretching of the fabric. And the fabric! The first time, when my chastity was unlocked, I wasn't sure about covering my small penis with it. Now, it only deepened my feminity. I think I will resign from wearing chastity just to feel the lace directly on my limp penis. But I can't parade just in my panties, so the top is needed. There was of course matching bra with a wide belt behind and with similar text on it, but since it was almost evening, I chose a pink babydoll with a black lace finish. The writing on the front, just below the breast line says 'Daddy's Cum Lover'. It was slutty. I felt slutty. But it was true - I love Craig's cum. I love when he fills my mouth or my ass, I love the taste of it, the texture and volume he produces. Wearing these clothes made me realize, that I want his hard member in my mouth right now.

I applied red lipstick and I left the bathroom to show myself to Craig. Now, his eyes widened when he saw me in my slutty bedclothes, and I started sucking my finger. His boxers went off faster than Road Runner in Looney Tunes, and I was kneeling in front of him, stroking his cock again. I didn't have to be persuaded, or convinced in any way - I was already tasting a massive drop of precum from his cock, closing my eyes and moaning in ecstasy. His solid chunk of meat felt incredibly warm inside my watery mouth. For a minute or so, I just kept it inside, not bobbing, sucking, or doing anything else - my lips were just wrapped around it, and I was just simply bonding with it, enjoying every second of me being on my knees. Craig brushed my hair with his fingers and gently grabbed the back of my head, slowly impaling my head on his cock on and off. I understood the allusion and started doing my work, giving him maximum pleasure. A couple of minutes later, we changed the position. He lay down on the bed, and I, as a devoted girlfriend, crawled towards his member, trying to grab it without using my hands. And I succeeded, which lead me to give him more and more head. Not soon after, my knees were sore enough, so I sat on the bed, letting him stand in front of me. Now, I was giving a blowjob sitting, slightly leaning toward Craig's body.

Many bobs later, he silently grunted, and slowly filled my mouth with the sweetest nectar of his semen. I was swallowing every single drop of it, but I was hungry for cum that night, so I twirled a few times with my tongue around his glans. The effect was very predictable because, with every twirl, his cock twitched and spurted another glob of sperm on my tongue. There was also a side effect of this, because, with every twirl, the corners of my mouth opened a little, letting Craig's cum cover my chin and drop on my thighs. In fact, it wasn't a side effect at all. I loved to have sprayed face with Craig's white, sticky sperm and I always wear it with pride and belief of my job done well. When I finally let him pull out his cock from my mouth, it was almost purple from the pleasure I gave him. But I continued my seduction by looking deeply in Craig's eyes, as I scooped everything from my chin, and licked my fingers clean. He only smiled and fell on the bed next to me. We cuddled afterward.

"Diana, you are the most amazing girl I ever had."

"Thank you, but what about Rebecca?"

"Rebecca, yes, she is an amazing woman, and I love her with all my heart, but your personality and talents are... exquisite! But if you had an opportunity of going back and changing anything..."

"I wouldn't."

"You sure? What if you could stay in 'guy mode'?"

"And what is the purpose of that? From the moment I met Rebecca, I started to wear nice clothes. Not hoodies, not sneakers, but really nice clothes. And from the moment I've met you, I finally feel good in bed."

"I see. So what was your love life before?"

"Before meeting Rebecca? It was a single life. I was only watching porn. Tons of it."

"What kind of porn?" He asked smiling.

"Mostly vanilla, I had some favorite pornstars to watch."

"And what did you like when you watched it?"

"I loved to admire the girls. Their lingerie, heels, and heavy makeup. The way they sucked a dick, how they rode it. I loved the moments when they received a facial and were happy about it."

"Have you ever imagined being that girl?"

"No never."

"Why is that? You didn't resist much when Rebecca told you to put on your first pair of panties."

"Yeah, I know, this is really messed up. I loved to watch it on a girl in the movie, I imagined myself stroking her thighs covered in stockings, or touching the lace panties just above her vagina..."

"See? I think your subconscious was silently telling you that you want to wear them. You never experimented as a kid or teenager?"

"Frankly, I remember one particular thing. When I was around thirteen, I went into a bathroom and saw my mom's lipstick on the mirror shelve. I took it involuntarily in my hand and opened it."

"Have you applied it?"

"No, of course not! But the moment when I screwed it out, and when I saw the burgundy color of it, I was hard in a second. I just masturbated in front of a mirror, holding lipstick in my other hand."

"Another silent sign from your subconscious. You should have applied it back then. By the way, your lips looked super lusty tonight. And it was an incredible erotic view to look down and see them wrapped around my cock."

"Thanks, it was a pleasure."

"Indeed! So... If you want, go brush your teeth and we will go to sleep. I have to wake up really early tomorrow."

"Okay, but what should I do when you'll be gone?"

"There is one thing. And it's a surprise from Rebecca and me. But you will get to know more tomorrow morning."

I said 'okay' and went to the bathroom. The very sticky panties and stockings were waiting for me in the sink, so before brushing, I had to wash them quickly. The feeling of partially dried and cold sperm on these clothes felt strange, but I wasn't disgusted at all. Eventually, I started brushing my teeth, and when I finished, I noticed two globs of Craig's semen on my thigh. Without thinking too much, I scooped them and wiped my finger on my tongue. Fresh teeth with a salty taste of cum, that was all I needed after our evening. When I get back to Craig, he was already sleeping, so I cuddled him and fell asleep too.

I woke up in the morning. Craig was already gone, based on the empty hanger where his suit should be. But I found a medium-sized envelope on the table. There was a printed small logo 'Day1' on the front. I was really curious about that, so I opened it quickly. The first thing was a note.

"Hello, Diana. Because we both love you so much, we have this unusual gift for you. The only thing you have to do is to go to the address printed below. We hope you will like it." Signed by Rebecca and Craig.

And there was a full address below.

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11 Comments
AnonymousAnonymous4 months ago

Pleasee continue with this story. I'm in the process of feminization myself with the guidance of my best friend (she has no sexual interest in me) and i would like to live vicariously through Diana.

ideasforwife84ideasforwife844 months ago

Loved the story. Please continue..

theresa628theresa62810 months ago

Need part 12 tSo can read about 1st day in NY.

JackiemichelleJackiemichelle11 months ago

Wow. Loved the story. I wish it was about me. I hope you finish the story. Couldn't stop reading

RachelPrRachelPrabout 1 year ago

I am so loving this. Please continue this story. I would love to see how their relationship builds and to know what's in store from "Day 1" through the rest of the week.😘

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