tagTransgender & CrossdressersA Boiled Frog Pt. 05

A Boiled Frog Pt. 05


First off, I apologize for the delay. I played hooky all summer and enjoyed the great outdoors. It did give me time to map out the story in my brain. Hopefully, now I can get it on paper quicker. This time I need to thank Misty F and Son of Battles for going through Part 5. Again, please vote or favorite the story if you like it, that's the only payment I get.

Chapter 1

Here I was, laying on a couch, with two of the most beautiful creatures on the planet. I had just had my first threesome and was feeling special. Just a few short weeks ago I never dreamed that anything like this was possible, in fact I firmly believed I would go through life with only screwing one woman period, never two at once. Of course, I never dreamed I would have tits on my chest either. But the world never works the way you want it.

And then I had to open my mouth.

"Ok girls, I need to know," I said "Tell me one thing that you guys have planned that I don't know about. Just one. I don't think I can handle it all at once. But right now, I think I can handle one thing."

The girls looked at each other, then nodded to one another.

Hesitantly, Lisa spoke, "If it's okay with you, of course, we have you scheduled for breast augmentation surgery on Thursday."

"Um, what happened to the injections?" I responded. "Didn't we decide to go that route? I specifically remembered stating that I wasn't comfortable with augmentation."

"But you're not gaining weight," Julie piped in. "Lisa hasn't been able to do even one injection. I don't think its viable because your metabolism is just too high."

"Let me think on it, that's a pretty drastic step," I said. At first, they protested, but when I got firm, they both nodded at me, for the first time seeming unsure of themselves as I didn't cave in immediately.

After a couple of minutes, Julie got up and headed to the restroom. The moment she left the room, Lisa vaulted into action. She was out of the cuddle and on her knees with my still flaccid dick in her mouth trying to revive it.

"Um, Lisa," I said. "I'm okay right now and don't need a repeat. That was pretty good."

"I didn't get my turn on this dick," she declared. "I get to ride you now."

I glanced over to where Julie had headed, knowing she was in a fragile state, but Lisa was pursuing her case with an abundance of passion. My cock knew what it wanted, as it was rapidly gaining length and girth from Lisa's administrations. Once I was hard, she quickly got up and impaled herself. I laid there letting her do all the work, thoroughly enjoying myself.

As she got into a good rhythm, she began issuing orders.

"I need you to come home with me after this. Ash is worried about us since you weren't in my bed last night. She kept asking where you were. I need a good performance from you tonight so that she can report back to my parents that we are still in love and things are going well."

"I can't tonight," I said. "And I don't think that's why Ash was asking about me. You saw the fragile state Julie is in. She needs me tonight. I am sure you understand, right?"

I could see Lisa's eyes harden. She kept saying she was willing to be second fiddle to our marriage, but part of her always liked to be in control.

"Jules is tough, she will be fine," Lisa declared. "But I NEED you. You have to do this." She then went on with a laundry list of reasons of why I needed to take her home and fuck her loudly.

I'm such a sucker. I could feel myself capitulating and I had just said "Fine" when Julie walked back in.

Julie looked at Lisa going up and down on me and I looked for jealousy and saw none. In fact, it was the opposite -- her eyes were lighting up with lust. I guess she was really okay with me fucking Lisa. Did she still love me? I mean if I had walked in on her and Mick I would have thrown a conniption fit. Did that make me immature? I told myself I would have to think on this later as right now it was becoming harder and harder to concentrate on anything with Lisa's Kegel exercises working wonders.

Julie came up and started making out with me as Lisa rode her way to orgasm, both hers and mine. She was kissing me and backing off and whispering sweet nothings to me, telling me how much she loved me and cared for me and would do anything for me. I whispered back to her that I felt the same way and her beaming smile filled her face and my heart with joy.

After we were truly done, I mentioned to Julie that Lisa needed me to go with her tonight. Julie immediately got upset.

"No, I need you with me tonight," she demanded.

I looked over at Lisa and her eyes were pleading with me.

I turned back to Julie and said, "What do you need me for? Lisa has Ash and doesn't want to break cover."

"I don't want to be alone," she pouted. "Please be with me, Chris."

I was surprised to hear that name from her. Lately, she had only been calling me Tina.

I turned to Lisa. "How bout we all four go to dinner since Ash knows Julie is my roommate? Then after dinner, I can go home with you, put on a performance for Ash, then slip out and say I need to work early so I am going home. Then I can rush home and be with you Julie. Would that work for the two of you?"

Both girls spoke at once. Lisa stating that she wanted to wake up in the morning with me and Jules asking what she would do while waiting for me to finish with Lisa.

"There is only one of me, girls," I pointed out. "You two are going to have to learn to share. You guys are the ones who put me into this mess, you have to deal with the consequences."

Puppy dog stares was their response. I knew it was my decision. I preferred just going along with whatever my wife wanted and whatever Lisa wanted. But I guess at some point, I needed to take control. And yet, I am so weak. I punted the decision down the road a little further.

"Lisa, go home and put on something sexy. Me and Julie will run home and change and then pick up you and Ash and we'll hit Tru tonight, all four of us. Then we will see how the evening goes before making any more decisions."

The girls seemed okay with this plan and we headed out, agreeing to meet up later.

Chapter 2

The girls looked amazing. All four of them. Yes, I am including myself in that mix. Julie surprised me by pulling out a new sparkly blue dress that she had bought me. It was backless so I could wear no bra. I still had enough boobage for them to jostle around enticingly under the material, marbleizing my nipples in the process. The dress also came with a new pair of matching 4' inch stiletto heels.

Lisa was in a classy cream-white evening gown that was tight against her neck giving off no cleavage but cut sharply down her sides which emphasized her bosom even more. The dress went all the way to the floor but had slits that showed her legs when she moved. She looked elegant and worth a million bucks.

Julie went with the little black dress, but one that looked spectacular on her. It made me glad I had locked my penis up in the femini girdle because otherwise I would have tented my dress for sure. She oozed sex appeal.

And Ash had gone all out. Her dress was a red Chic Me sexy backless halter neck-plunged dress that exposed most of her flawless skin. The plunge line in the front went at least three inches below her breasts and I could see everything but the nipples. It was cut all the way to her waist, so when she walked I could drool over her long legs. And she had on the highest f-me heels I had ever seen, coming in close to 6' inches.

Needless to say, the three of them were all dressed to emphasize their sexiness and draw interest. In fact, it was a guarantee that every male eye focused on us as we walked in the restaurant. We had barely been seated when the first male approached, an alpha male Adonis who zoomed in on Lisa, who was obviously the most expensively dressed of our bunch.

She blew him off with style and precision, obviously something that was rote to her. I studied her while she did it, since I figured that was a skill I needed to develop if I was going to continue as Tina, which seemed more and more inevitable as each day passed. I then watched Julie do it a few minutes later, and even Ash got a chance to turn down a guy before the dinner was done. No guy approached me, which I was thankful for.

At one point, I felt a foot graze my leg. Someone had kicked off her heel and slowly dragged her foot from my ankle and upwards to my knee before pressing forward. From the angle of the attack it had to be Ash who was sitting across from me. As she nuzzled her way towards my crotch I reached down and grabbed her foot, holding it away from my groin and started to massage the balls of her foot. She smiled at this and smirked at me. This girl was trouble.

But as I sat there and enjoyed the company, the flirtations and the food, it dawned on me how impossible this was. There were more than 50 guys in this establishment, and I was with the three hottest girls in the place and all three of them was interested in me. Wimpy, little Chris. Maybe being Tina wasn't so bad after all.

Ash had a plane to catch in the morning so I suggested we all head over to Lisa's place for a nightcap and to stop the procession of hopeful men. Even before we left the table, Ash announced, "I want to ride one more time in Tina's new car, so I am going to ride with her."

Luckily, I had foreseen this possibility and honestly told her, "Sorry, Ash, but I rode over with Julie. She drove."

Disappointment shone through her face and she was silent as we split up and headed to our vehicles. Julie walked with me, although she restrained from showing any PDA until they were safely out of sight.

She grabbed my arm and pulled herself in close as we walked. Her tone was flat as she said, "You are going to spend the night with Lisa, aren't you?"

"Actually, I am not," I replied. "I really do want to be with you. We are going back to Lisa's pad where I will perform, as you to put it, for Ash. Then me and you will go back to our place where I can spend Sunday with you."

She snuggled in closer and kissed me before we separated to get into her car.

Once we were buckled in and heading out of the car garage, she switched subjects.

"You could fuck her, you know," Julie stated.


"No, Ash," she responded. "She wants you bad. It's pretty obvious."

"I know," I replied. "She tried to grind her toes into my groin during dinner. That's why I had you drive. I can't be alone with her right now."

"I am okay with it," she said. "I give you my permission. She certainly is cute."

"Honey," I glanced at her in astonishment. "I can't do that. I mean that's Lisa's little sister. That's just wrong on so many levels."

"Wouldn't that be hot, though?" she mused. "Imagine doing them both at the same time. I get goosebumps just thinking about that. You would be such the stud. How many guys actually get to be with two sisters, especially two of that caliber?"

"Not very many, that's for sure. In fact, I don't think there are too many sisters that hot out there, period."

"Just think about it," she requested. "I would love to watch that."

Thoughts trickled back to what I heard Deidre and my wife talk about in the diner. It did seem like my wife was delving into pornography. Where else could she be getting these ideas? Yet, I never saw her doing it around me, so I couldn't be sure. In fact, she was barely ever on our home computer.

While I was contemplating her response, we made it to Lisa's place. Lisa and Ash arrived simultaneously and all four of us walked up together. Once inside, Lisa headed for the kitchen for wine and Ash said she was going to slip into something more comfortable. Julie and I went into the living room where Julie turned on the TV and started pulling up Netflix.

Ash returned in lingerie. It was see-through and I could see her nipples were erect. She then sidled into the couch right next to me, effectively forcing everyone else to sit away from me. Then dramatically, she called out, "What we watching? I hope it's something sexy."

She then leaned into me and whispered, "It's my last night in town. I am hoping for some good memories. Don't let me down!"

I looked at her and glared, but I kept my voice to a whisper as well. "Ash, you need to cut this out. I told you I am unavailable and I meant it. I can't cheat on Lisa. I just can't. You need to let me be me. As I told you in Vegas, I need time."

She pouted.

I had to give the girl one thing. She was like a heat-seeking missile once she had locked in her target. Unfortunately, that target was me. I didn't know how to handle that.

I quickly stood up when Lisa entered the room and went to her and kissed her with a peck on the lips. Then I waited for her to sit down and sat right next to her, on the opposite side from Ash. Ash smirked at this and blew me a kiss.

The movie started but I couldn't focus on it. After the first 20 minutes, I got up and went to the bathroom. There, in the bathroom, I took the time and hassle to remove the femini girdle since I was supposed to 'perform' later. Coming out of the bathroom, Lisa was waiting for me. I guess that time was now.

As we entered her bedroom, light leaked in from the full moon and Lisa didn't bother to turn on any lights. She turned her back to me and asked me to unzip her. As I pulled down the zipper, exposing her back, the moonlight danced across her flawless muscles. It reminded me of Vegas, and the magic I felt there.

I leaned forward and kissed her scapula lightly, continuing to peck as she slowly turned around to face me. My pecks went from her scapula, to her bicep, to her breasts. Avoiding the nipples, I gave each of her breasts a light peck before raising up to her mouth. She still had her heels on, so she towered above me and I had to strain my neck to reach those luscious lips of hers. She took pity and leaned down, opening her mouth to meet mine. Her hands simultaneously grasped the spaghetti straps that held my dress up, pushing them off my shoulders and pooling my dress onto the floor.

After I pulled away breathless, I whispered to her, "You are wonderful."

She giggled.

"I was thinking the same thing about you. Thank you for choosing me tonight."

"I am going to go home with Julie," I said. "But let's not think about her, let's focus on us."

She had only panties and heels on after the dress had been removed. She wore no stockings tonight. I slid down to my knees and tugged the panties down. She stepped out of them for me, and as her legs split, a rich aroma drifted towards me and I jumped at the opening provided.

My tongue lashed at her clit and I saw the rivulets of moisture already starting to run down her legs. She was ready for me, strong with desire. It amazed me that this beautiful creature wanted me. As I tongue-bathed her, I thought back to our first meeting so many years ago. She had seemed too frigid then, controlling and cruel even. She was a distant memory of that now.

After a couple of minutes, she pushed me away and climbed onto the bed to lie down. As I followed, she grabbed me and pulled my head back into place, this time controlling my head so that I'd focus on her clit. I felt her getting close so I started to slow down.

She whimpered.

"You're going to torture me, aren't you?" she gasped. "Can't I please just have this first one?"

I pulled my head back. "You know it's better if you wait."

"I hate waiting," she growled.

I ignored her protests and continued to tease, stretching out her pleasure and bringing her slowly to a boil. After the third time of bringing her to the brink, I succumbed to her begging and brought her to a very loud screaming climax.

I heard the door knob twisted but Lisa had locked the door. Then we heard giggling outside the room. They must have heard Lisa cumming and came to investigate.

I yelled out, "We are fine in here. Everything is okay."

Lisa shouted out. "More than okay, even."

I heard Julie's reply. "Have fun, you two. Don't mind us out here."

Lisa shouted back. "We won't."

She then climbed onto me and said, "My turn to tease."

She slid herself down onto me and started to rock. She started to squeeze her inner muscles and milk me. As I felt the pleasure build, she slowed down with a smirk.

"It's better if you wait," she teased. "In fact, let's see how long we can draw this out. Three hours, four, maybe we should have you come just as the sun rises."

"You would be bored by then," I teased back. "In fact, the first time it starts to feel good for you, you will lose all control and bounce like a pogo stick."

"A pogo stick, huh," she said. "I will show you a pogo stick."

Her hips started to thrust down with emphasis, slamming down into me and causing the bed to bounce. I moaned. My eyes were riveted to her breasts, those huge monsters were flying all about. I wondered if she would hurt herself.

"Oh, you like that, do you?" she snarled. "Does my little Tina like my pogo stick skills?'

"Uh, huh," I gasped, getting close.

She lifted herself completely off me and started to climb out of the bed.

"Too bad."

It was my turn to snarl. I dove at her, wrapped my arms around her and speared my dick back into her pussy from behind. I then proceeded to do my best impression of a jackhammer as I pistoned rapidly over and over into her.

She laughed and thrust back into me. It was exquisite. My release came quickly and I dumped into her. She fell back onto the bed, turned over and snuggled into me.

"That was fun," she whispered.

"I agree," I added. "We need more fun in our lives."

"Agreed," she said, sighing.

I started to pull away from her to get up, but she clung to me.

"Chris, please," she whispered. I was surprised to hear that name from her. It had been a while since she had called me that.

"Yes, love?" I responded.

It was a miracle to see her hesitant but she was struggling to get out her thoughts. I had never seen her looking this vulnerable before.

"Please don't," she begged, looking at me imploringly.

"Please don't, what?"

"Please don't sleep with my little sis," she finally breathed. "Ash asked me earlier today. She really wants to be with you. I don't want to share you. It's bad enough I have to share with Jules."

Heat boiled into me.

"Then what the hell was all this Mick stuff about," I asked. "Julie told me you helped plan it all. And that was after I confided in you I wasn't interested in guys."

"Julie insisted," she eked out. "She said it would help you be a better Tina."

"I guess I need to go have a heart-to-heart with her." I kissed her on the forehead. "Go to sleep. I am going to go take Julie home and say goodbye to Ash. I will see you tomorrow?"

"I can't," she said. "I know it's Sunday but I have to fly out for a meeting in Boston. I won't be home until Wednesday. I guess the next time I will see you is in the operating room on Thursday."

All the tension that I had released through sex immediately returned and I felt my shoulders knotting up. I didn't want to get into that now so I just nodded and kissed her again before leaving the room.

As I walked down the hallway to the living room, I heard voices. Curiosity had me slow down so I could eavesdrop.

I heard Ash's voice. "Admit it," she accused. "You like her just as much as I do. I am just more open about it."

"What makes you think that?" Julie responded with. "Whatever gave you that impression? Tina is my best friend."

"I saw the way you were checking her out tonight," Ash countered. "You looked like a bitch in heat."

"I could say the same thing about you."

At that point, I didn't want a catfight to break out so I appeared.

"Please, ladies," I said. "I was the least attractive one at that table and both of you know it."

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