Rebecca's Ch. 10

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Diana gets to know what real man is.
5.6k words
4.81
14.4k
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Part 10 of the 11 part series

Updated 06/10/2023
Created 08/14/2021
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I followed his instruction without any hesitation. With my hand in his pants, I grabbed his flaccid penis and started to pull it out slowly. It was the first time in my life when I held another man's penis in my hand. It was warm, and even if he was flaccid, I could tell he is thick. At last, he was out. It was at least seven inches, and still, it wasn't hard. Circumcised, the head was the size of a small peach.

Playing for the last few months with toys, I knew what to do with my penis. Although, the feeling of warmth of the real skin and completely different flexibility of it felt much better than rubber toy. I started stroking it slowly, looking at how it grows. After a few minutes, flaccid seven-inch turned to ten-inch cock, standing in less than the thickness of my small finger in front of my face. I looked up, deeply into Craig's eyes. He smiled at me, which told me that I am doing good. Then I looked at Rebecca who was sitting on the leather chair. She nodded, giving me some kind of approval. My stress and excitation were on the same level.

I started to open my mouth, and slowly moved toward Craig's penis, which resulted in my lips touching the head of it. I squeezed my hand on the base of his dick and stroked my hand toward the head, to feel as a big drop of precum touched my tongue. At this moment I realized, that I have a penis, another man's penis in my mouth, and I'm enjoying the taste of his precum. I licked the base of the head and started to move my head down his shaft. I took maybe half of it when I felt it touching my throat. I also noticed, how veiny it was, since I didn't notice it when it was flaccid. Again, I looked into Craig's eyes, while I bobbed my mouth up, and slow down again. I could feel constant twitching in my cage.

After a few minutes, Craig gently grabbed my jaw, to tell me I should stand up. Turning me around, he unzipped my dress, which dropped down to my ankles. I quickly stepped out of it, as Rebecca approached and started playing with the band of my panties. It was another signal for me, and I took the panties down. Doing that, I obviously had to bend over, and I didn't miss the chance of feeling Craig's big penis in my mouth again, but only after one bob and a quick lick, I did stand up again.

Craig looked at me, from top to bottom. I think he liked the view of me in the veil, white lace bra, garter belt, stockings, and heels. He knelt and started touching my chastised penis.

"It is so small," He said.

"Yes, it is" I confirmed.

"You don't feel like a man, don't you?"

"No, I don't," I said with confidence.

"Do you feel like a girl?"

"I do."

"That's the right words for a bride." He smiled. "Would you like to feel like a woman?"

By saying that, he slowly started caressing my testicles, and moved to my ass, feeling the base of a butt plug. I felt the rush of emotions as I blushed.

"What do we have here... Do you like the feeling of the plug?"

"A lot..."

"You know, it was my idea with this particular chastity and a butt plug."

"Really? Rebecca didn't say that." I looked at her, and she was genuinely smiling at me.

"It meant to be a surprise," Craig said, grabbed the base of the plug, and pulled it out. "Do you want to feel something better down there?"

"The only better thing there will be your massive cock." I replied.

He smiled, stood up, and kissed me in my mouth again. During the kiss, I couldn't help, but stroke his dick up and down. Eventually, he broke the kiss, grabbed my hand, and guided me to the sofa, instructing me to lay on my back. He climbed on me and started kissing me again. His penis started to rub against my chastity, my testicles, and my anus. When I opened my eyes, I saw Rebecca standing next to us, with a big bottle of lube. Craig took it and squeezed a big amount of it just above my asshole. He started to rub the lube all around my ass with his penis, which was extremely erotic for me. I started to quiver.

My quivering was like a green light for him. Craig placed his cock a the entrance of my hole and didn't rush to push it in. Thanks to the butt plug, and of course the lube, my sphincter didn't resist and the head of ten-inch cock was already inside me. My quivering stopped and I moaned loudly.

"Now you'll become a real woman Diana." Craig said.

"Yes... Please make me a woman..." I whispered straight to his ear.

Craig started thrusting, and my hungry ass was swallowing his penis inch by inch. The feeling of being full was amazing, and ten inches rubbed so well on my g-spot, giving me heaven-like pleasure. During the thrusting, Craig started to kiss my neck, which only intensified my pleasure.

After a few long minutes, Craig pulled out, and I noticed a lot of white goo on his cock. I looked down to see my small clit-like penis is leaking. We both stood up, and Craig told me to get on fours.

With my ass in the air and my face buried in the pillow, my fresh lover placed himself at the entrance again. I couldn't see, but I felt how he is filling me with his meat. This position wasn't so passionate as a missionary one, but Craig started to thrust faster and faster, vigorously fucking my ass. I screamed in pleasure, and Rebecca only encouraged me to enjoy and scream as loud as I can.

After another few long minutes of fucking, Craig slowed down, bent to my ear, and whispered: "Are you ready to embrace your womanhood?" "Yes!" I screamed in pleasure, and he regained his pace once again. A few thrusts later, I felt that he stopped, and his whole body tensed. At the same time, I felt his penis pulsating, and the warmness started to appear inside me. He was filling me with sperm!

But it wasn't like my cumming. Two or three shots and it's done, oh no. He was cumming a lot, and when he was stopping, he thrust a few times more and cummed again. Finally, he stopped and pulled out.

A massive volume of his sperm flowed out of my butt, covering my testicles and chastised penis. It was running down my thigs, completely soaking the lace tops of my bridal stockings. It felt incredibly slutty, but I loved that feeling.

"You are a woman now." Rebecca said. "How do you feel after being taken by a real man?"

"I... I don't know what to say. I feel good, very feminine." I stood up and continued: "I'm happy that it happened."

"That's it?" She asked shocked by my answer.

"Yeah, I mean, no! You know, I was quivering when Craig kissed me on the neck, but when he placed his dick in front of my ass, I was so stressed."

"But a moment later, you were cumming on him!"

"Yeah, I came, I mean my cum dripped out, but I didn't feel an orgasm."

"Really?"

"Really."

"But it was a pleasure for you?"

"It was a great pleasure. but I think it's because it was my first time and I was stressed so much. Although I enjoyed a blowjob."

"I see. So what exactly do you enjoy giving a blowjob?"

"You know, I was on my knees, wearing bridal lingerie, touching his veiny cock with my hands, and giving him pleasure with my mouth. It made me surprisingly horny."

"You thought that he will cum that way?"

"I did."

"Sweetheart, there will be more opportunities to make Craig cum with your mouth, trust me. Now I think you need a shower. Just put the clothes in the laundry bin."

And I went to the bathroom. I could feel not only the lace tops of my stockings were soaked, but the rest of the thigh length of the stockings, right to my knees too. I took off the heels and slowly rolled down the hose. They were so sticky! Craig's sperm was definitely much more fat than mine. I took off my bra and garter belt too, and I went under the shower.

I started cleaning myself, especially my butthole and my legs. Almost everything between my ass and my knees was in cum. When I managed to clean myself decent enough, other globs of white goo flowed out of my butt. It was the proof, that Craig is cumming a lot! I decided to push out the rest of it forcefully and finally finished showering. I dried myself, and I noticed a small pile of fresh clothes in the laundry bin, including a tiny toiletry bag on top of it. In the pile were purple panties with lace trims, and a bra in the same style. Under them, were laying a pair of jeans with a white baggy T-shirt. I put it on and opened the toiletry bag. There was a dark eyeshadow, mascara, and red lipstick, so I quickly applied it to my face.

When I went out, Craig was sitting on the sofa, where my ass swallowed his dick half an hour ago. He was sipping scotch on rocks, but soon as he saw me, he stood up, came to me, and kissed me deeply. I could feel the taste of the scotch, but not for long since he broke the kiss and said:

"That was amazing Diana! You were so amazing!"

"Thanks. I was stressed, so I hope we can redo that some time."

"I'm sorry if I did something wrong." He said.

"Oh, no no, it's not your fault Craig. I was incredibly stressed by this situation. I hope next time will be better."

"I'm glad you are saying about next time. I was a little nervous that I hurt you somehow, you know, by that face pace at the end."

"No, of course not. It was a pleasure to take your big cock like that." He grinned. "There was a lot of your sperm too! I couldn't clean it off!"

"Yeah... I was told that I cum a lot..."

"Maybe someday I could taste it..." I said, and I felt like a flirting whore.

"I'm sure you will Diana, I'm sure you will."

When we both talked like that, from the corner of my eye I noticed that Rebecca started masturbating to our conversation. She was almost laying in the chair from which she observed my sex with Craig. I couldn't resist and I came close to her, kissed her lips, knelt down, and started penetrating her beautiful vagina with my tongue. She came in no time, making the leather chair wet with her juices. I started cleaning her pussy from the juices, as she stood up, so I could get more of it. I was happy that I could eat her like that. Rebecca went to the bathroom to clean, and I was sitting in the middle of the room with ruined makeup, then Craig said:

"If you will give me a blowjob, in the same way, I'm looking forward to it." I smiled back at him, and I went to the bathroom to 'powder my nose'.

When I entered the bathroom, Rebecca was drying herself already, and I started fixing the mess on my face. "Let me, I love doing this to you" I heard, and she stood completely naked in front of me and started doing my makeup. When she finished, she said that it was time to see the rest of the house, so I followed her upstairs.

At the top of the stairs was a wide corridor with four doors. The first door on the left was another bathroom, much bigger than the one on the ground floor. It has a shower for two, a large bathtub, sink, toilet, and bidet. The floor was in the sand color, with stripes on the wall that looked like it's made of wood. We left the bathroom and went through the opposite door. It was the master bedroom, with a king-size bed in dark purple sheets. There was a smaller room inside the master bedroom, which turned out to be a walk-in wardrobe! Rebecca loved to dress sexy, and now it was clear how much of sexy clothes she have. Racks with dresses, skirts, and blouses, drawers full of bras, panties, and stockings plus shelves with heels. I was shocked.

"Do you like it?" She asked.

"Sure I do! It's amazing!"

"I knew you will. You can come here to borrow anything you want."

"Thanks, Rebecca!"

"Okay, let's go to the next room."

The next room was also the master bedroom which confused me a little. I asked Rebecca about it.

"You see, Craig and I are not sleeping with each other for a longer period of time."

"That's... sad."

"Yeah, a bit. But meeting you, changed our lives. It's not sad at all at this moment, we are very happy that we've met you."

"I'm happy too!"

Rebecca kissed me on the cheek and continued: "This is Craig's bedroom. He has a walk-in closet too with his suits, but don't borrow anything from him." Rebecca giggled.

"As I would like to wear a suit!" I laughed.

"Let's go to see your room."

We went to the opposite door to Craig's bedroom. This room was much smaller than the bedrooms I was in before. It was maybe twice the size of the walk-in closet. It was painted in light pastel shades of pink, with similar closets to the Rebecca's on the one wall. The closets were full of very feminine clothes and heels, and in front of a window, there was a large desk, with two twenty-seven-inch screens attached. I realized that this room was meant to be mine.

"Do you like it, Diana?"

"Yeah, it's amazing! So many new clothes... And you bought the desk with screens!"

"You are welcome, darling."

"Rebecca, but I don't see any bed here, why is that?"

"Oh, yes. We have two large bedrooms, with king-size beds. I think it will be best for all of us if you will sleep with me, or with Craig. I think that after sex, you won't leave me alone for the whole night?"

"No, of course not. And it makes perfect sense."

"Okay... I will leave you now, so you can unpack the rest of your things."

And so I did. I've unpacked my clothes and figured out where is what. I had large drawers of lingerie, dresses, and skirts like Rebecca, but my collection of shoes was definitely smaller than hers. I didn't complain, since they bought a lot of new pairs of heels for me, not counting the clothes. After unpacking, I connected my workstation to the screens and turned it on. Luckily it survived the movement so I could start working the next morning.

After unpacking, connecting, and sorting things out, I went to the bathroom, to meet Rebecca there. She approached and kissed me. whispering to my ear: "I have a surprise for you. Strip naked." Then, she grabbed the small device, and from its shape, I thought it was the newest pair of AirPods, but she attached it to my chastity, and a moment later the chrome-pink tube fell off.

"I thought you said it can be opened with an industrial-grade magnet."

"And it is that kind of magnet honey. You don't think I would lock you for the rest of your life?"

"Well... I accepted that idea."

"Really? I'm impressed that thinking like that you've agreed to it."

"I mean, I love you and I trust you, and I thought you are doing this because you want the best for me."

"Of course, I want the best for you! And I love you too Diana!'

We both hugged for a while, and after that, I looked down at my unlocked penis. Now it was like two inches long, and Rebecca explained to me, that long-term chastity can cause that. I wasn't concerned, because I didn't use it for sex anyway, but Rebecca started kissing my nipples, and I think my penis was aware it was out of the prison. It was hard in a second, but three and a half inches of oversized clit was nothing when I thought about Craig's ten-inch cock. Rebecca noticed that I am hard, and started stroking me, using only two fingers.

"You are so small, Diana... It's so cute that you are that small... I bet that you are thinking about Craig's penis, right?"

Damn, she was right. I was thinking of giving him a blowjob and how easily he pushed his penis inside my ass. Rebecca lowered to her knees and took my small pecker in her mouth.

"It shrank a lot, Diana... It passed my teeth and touched my tongue. Can you feel my tongue?" I nodded. "Does it feel good? Imagine how Craig felt when his massive dick stretched your jaw and filled your mouth... You loved that, huh?"

And I came. Few little spurts inside Rebecca's mouth, with the thoughts of giving a blowjob to a real man. I realized that I came by stimulation of my penis, which didn't happen for almost a year. Anyway, it was a good orgasm, but far from the one that I experienced last week, riding my dildo. She sucked the rest of the goo out of me and stood up to share the load. I started kissing her, to receive the sweet taste of my own cum. When the kiss ended, Rebecca said:

"It was clear from the moment I have met you, that you will enjoy eating your own sperm. But you will love Craigs massive loads. Let's shower and go to bed. Today you will sleep with me."

We showered and dried, and Rebecca gave me a black lace babydoll with matching panties. When I slid them on, I felt very nice feeling fabric on the skin of my penis. Then I remembered, that Rebecca forgot to lock it up again.

"Darling, you don't need chastity anymore."

"What do you mean?"

"It was needed for the whole process of your feminization. Also, it had to push you toward toys, and finally Craig's penis."

"That sounds like creepy mind control, don't you think?"

"Yes, and I am very sorry for that. As you see, everything turned out great, so don't think about it anymore. It was the only time when I did something like this, and I promise I will never do anything similar again."

"Yeah, but what if it turned out bad?"

"Honestly, after our fight, I thought it was over. And I thought to send you this magnet so you could unlock yourself, and maybe go back to your normal life."

"I see. Anyway, I understood that living en femme is my normal life. I don't want to change it."

"That's good. If you want, you can wear chastity, and sometimes Craig may want you to wear it. But as I said, don't think about it now, let's sleep. I love you, Diana."

"I love you too Rebecca." I said back, and we both fell asleep.

When I woke up, Rebecca greeted me with a kiss and told me that Craig already headed to the office, and she is leaving for her store too. We kissed goodbye, and half an hour later, I went to the bathroom to start my morning routine. When makeup was applied, I opened my new closet, full of feminine clothes. The worst, and the best thing is, that I didn't find a single sock, only stockings in various densities. I took one pair in lion color, rolled them up to my legs, and attached it to a silk black garter belt. Black panties and bra with lace trims, matching the garter were a perfect choice, and because it was a nice day, I chose a blue sundress with white polka dots. At the moment when I put it on, I realized, that it was very short, revealing my whole thighs, with lace tops of my stockings and stripes from my garter belt. But I didn't care. I ate my breakfast and started working.

Almost eight hours passed, and my eyes were exhausted, because of the new screens. I think that I will have to adjust their settings and lower the brightness. The sun in the sky wasn't covered by a single cloud, and it felt nice and warm on my skin. Remembering about a small pier on one lake, I decided to go for a swim and cool down.

I couldn't find any swimsuits in my closets, so I went to Rebecca's. She had a few of them, but all were two pieces, and her bras were too big for me. I took the red one, like in the 'Baywatch', slipped my feet in flip-flops, and went to the pier.

When I jumped into the water, I felt sorry for myself that I didn't think about checking the temperature of the water with my foot. It was cold. But as soon as I started swimming and my muscles started working, water-cooled down my overheating body. I was maybe a hundred feet away from the pier when I saw a shape waving at me. When I swam closer, I recognized Craig. He waited with a big white towel to help me dry.

As soon as he wrapped me in it, he kissed me on the lips in greeting. I kissed him back, and I didn't even realize it when we started making out. He was stroking my thighs with his muscular hands and squeezing my ass cheeks. Soon after that, he moved Rebecca's bra I was wearing to the side and started kissing my nipples. I've become incredibly horny, with a small tent on my bikini panties. I whispered "I want you in my mouth" to him, and I dropped to my knees, unbuckling his belt and dropping his pants.

His penis was half erect, maybe around eight and a half inches. Immediately I took it into my watering mouth and we both moaned in pleasure. I was bobbing on his cock forward and backward, still kneeling in front of him, like a cock hungry wife, while he was caressing my hair. Using my tongue on the basis of the penis' head, I gave him a lot of pleasure, hearing him moaning louder and louder.

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