Sissy Friends Forever Ch. 02

I walked into the lounge and encountered my half naked fiancée kneeling in front of the couch with her head between the legs of another man. She was enthusiastically sucking on his cock as he sat with his eyes transfixed on the TV. Neither of the pair seemed to notice as I silently slipped in. I sat down beside him and snuggled up, offering him an opened beer bottle.

"Ah, Birra Moretti," he said approvingly.

"Nearest I could find to something Italian at the store. Hope that's OK."

"Grazie."

"Prego."

I reached between his thighs and stroked Cindy's hair as she worked away. It was good to see her enjoying herself. The man she was sucking was Matteo, a gay male escort we both once hired. In more recent times he had become part of the family and a permanent fixture in our lives. This evening we'd invited him round to catch up on episodes of our favorite reality dating TV show and he let us play with him as we watched. Sucking off a man wasn't cheating in our relationship, it was positively encouraged. We both adored giving oral, it was even better when we could do it together.

Cindy stopped what she was doing, looking like she was exhausted. She stood up on her heels in front of us and stretched. "My back is killing me."

"I told you to get smaller boobs."

"I wish I'd gone larger," she countered, looking down at herself. A couple of months ago she'd had breast augmentation. As per her typical style she had opted for the ridiculous. As well as being too big for her frame they were also far rounder than was natural, looking more like balloons that had been inflated on her chest, but that was exactly what she loved. She craved looking fake, it wasn't an accident or a case bad surgery, it was a deliberate aesthetic choice. Combined with her plumped up lips she was achieving the bimbo body she'd always dreamed of.

We'd both been on hormones for months, daring each other to keep taking them, and both of us were very gradually changing shape. I had the beginning signs of budding breasts and was slowly and very subtly morphing into a slight hourglass shape, but she was a million miles ahead of me in the transformation process. I was still straddling the line between male and female but she was almost pure woman, only a bump in her panties suggested anything could be otherwise. Her former identity of Chris was gone now and Cindy was blossoming in his place.

"What do you think Matteo?" She unhooked her hard working bra and pulled it off her shoulders, letting it fall to the floor before kneading her ample assets like dough. "Does this give you any ... inspiration?" she said sexily.

Matteo rolled his eyes. "Won't work honey," he said with complete disinterest. "You know tits do nothing for me," Cindy dropped her arms by her sides and look dejected.

"Something is definitely happening over here though," I said approvingly.

Cindy smiled, then looked in my direction and blew me a kiss. "Thank you babe." Cindy pointed accusingly at Matteo whilst addressing me. "That boy is being one tough sucker tonight. I must have been on his cock for ... what? It feels like I've been down there for like fifteen or twenty minutes or something."

"I am not a tough sucker," Matteo interjected, pointing his finger back at her. "The problem is you are not a tough sucker. You have no stamina."

"Can you take over, just for a few minutes?" she whined at me. I'd already blown Matteo an hour ago and had my fill of his cum. I was already a very satisfied girl and just wanted to snuggle him now with my favorite show.

"No. If you want the reward, you have to put in the groundwork. That's how it works."

"You got it easy. I should have gone first when his balls were full."

"Sucker." I stuck my tongue out and she snarled back at me.

"He's got me beat."

"Suck it up soldier and get back in the fight."

"I don't think I've got it in me."

"You'll never have it in you if you don't get back down on your knees."

"I know," she said unhappily.

"Sucks to be you."

She put her hands on her hips and studied Matteo's cock like it was her arch nemesis. "OK, I'll get it out of him if it kills me. I just need to build up my strength first."

"That's my sissy. Never give up. Never surrender."

Matteo's favorite reality contestant had just appeared on screen but Cindy was in his way. "Down in front!" he complained, trying to look around her.

"Drop for cock!" I commanded as I snapped my fingers. Cindy obligingly fell to her knees with her mouth wide open, clearing the view of the TV for Matteo. Her hypnosis was still as effective as ever, in fact she had been going ever deeper.

"That guy right there," Matteo said pointing at the screen, "fuck me he is hot. If I only had his lips around me now..."

"Hold that thought and use your imagination," I said. "Cindy sweetie, now's your chance. I think he'll blow his load any second now." She was still in a zombie state, staring into space with her mouth wide open. I placed my hand on the back of her head and gently guided her lips to his dick. She instinctively applied herself to the task with renewed vigor.

"What is it about him that's hot?" I asked Matteo. I had been trying to develop an attraction to men but it wasn't working very well, or even at all. I knew deep down I couldn't genuinely alter my sexuality but I wanted to be able to convincingly role play. I wondered that if I could authentically pretend I loved men, I might fool myself and my mind and body might somehow follow. It was like the idea that if you force yourself to smile when feeling low, it can lift your mood as your mind mirrors how your body is behaving. If I convincingly acted out attraction, maybe I would really feel attraction. I needed some kind of guide though, a mentor to help me appreciate the male form. "I mean I just have this kind of very vague sense that he's handsome. I know he is perceived as good looking, but what exactly is it that you think is attractive about his body? I just see... a gorilla. Describe it to me."

"I don't know, it's the way he carries himself, it's his smile, it's his .... " Matteo closed his eyes and finally came into Cindy's mouth. "He's just hot."

"That's not really much help." I'd have to get my education from someone more eloquent.

Cindy pulled herself off his cock and slumped to the floor. I gave her a round of applause for her hard won success. She clawed her way up onto the couch and collapsed beside me. I put my arm around her and tried to kiss her but she stopped me by putting her finger on my lips. "Thought you were going to steal my prize, did you? Bad girl. I worked hard for that." She very deliberately swallowed in front of me and licked her lips whilst looking into my eyes, then she removed her finger. "I'll have that kiss now please."

"Sorry I'm a bad girl, but you've been a very ..." I snapped my fingers "... good girl." She closed her eyes and retreated into a state of hypnotic euphoria, her mind triggered for pleasure at my suggestion. I gave her a long slow kiss whilst she was under. After about ten seconds she came around and put her hands behind my head, pressing me tightly against her face and we played with each other's tongues. She didn't want to let me go, but I eventually pulled away.

"That was amazing. That's so much better. I just woke up to you kissing me. It's like going from bliss into heaven. New house rule, I want a kiss when you use my good girl trigger."

"I'll see what I can do." I loved it when I discovered a new way to please her.

"Hey no kiss for the star of the show?" asked Matteo. I lightly pecked him on the cheek. "I've been ripped off," he complained. I compensated him with a proper kiss which was more to his satisfaction.

I turned back to Cindy. "Your lipstick has gone to shit."

"You really know how to charm a girl," she replied sarcastically and pointed at Matteo. "His cock is wearing most of it. Yours isn't exactly catwalk ready either."

"It's in the bedroom. Should have brought it through. But that means getting off the couch."

"I ain't movin'. We'll fix it later. So what did I miss?"

I filled her in on the reality show we were watching which had just started to reach a climax at about the same time as Matteo did. The show finished soon after and our Italian friend started making moves to leave.

"Can't you stay for one more episode?" I begged.

"No, I got to go. Work in the morning."

I reached out and held his hand, trying to stop him from leaving. "Please stay. Sleep in with us. Always room for you in our bed."

"No, I got to see a client early in the morning before he leaves town. Besides, if I stay here, one of you two cum vampires will try and suck me dry in my sleep again." He stared piercingly at Cindy, his glare amounting to a stern accusation.

"It was her I swear," she lied, pointing at me with her thumb.

"Tomorrow's cum is for paying customers only."

"We'll behave," I assured him. "Maybe."

"You know you are my two favorite ladies and I would if I could, but I really got to make a move."

"Come back soon. We miss you."

We both kissed Matteo and he left. We tidied up and made for bed. I had work myself in the morning. As I got between the sheets Cindy rolled over to face me.

"Tell me honestly, do you think I'm pretty?"

"Of course I ... " I paused sensing a deception, furrowing my brow. "Now why am I suddenly thinking of that Admiral Ackbar character from Star Wars? The one from the meme."

"Is it my fish lips?"

"No! It's a trap! I love hairy men and fat cocks," I said without any real conviction. She tried to cunningly deceive me with that question all the time and I invariably fell for it. I couldn't help but automatically respond that she was beautiful. "I want broad shoulders, a chiseled jaw, six pack abs, beards, that sort of stuff."

"Good sissy." She pecked me on the lips. "But you didn't love beards when I asked you yesterday. You're inconsistent which makes me think you could lying."

"Well I just decided I do today."

Cindy rolled onto her back. "But just imagine for a moment you were a heterosexual man, near impossible as that may be for you, would you find me pretty?"

"I would say you are the most attractive girl I have ever seen and you get hotter every day." She found my hand and squeezed it.

"Seriously though ... "

"I am very serious."

"I know my look isn't what you'd usually go for. I've been thinking. I want to change my body. I want to become the girl that you want. I want to be your dream, your fantasy."

I hugged her. She needed a lot of reassurance. "You are the girl I want right now, always have been and always will be. I want you to be the happiest girl in the world. I will love you whatever you want to look like."

"I'm too lucky to have you," she said. She rolled back over and we snuggled and kissed for a while. I started to play with her nipples and she flinched.

"How's the sensitivity going?" She'd been getting a little more sensitive, possibly from the hormones she was taking, but she'd also been trying new hypnosis to enhance the experience.

"Nowhere close to enough yet. I want my nipples so sensitive I can have a female orgasm just from a single touch."

"Well, I guess we should see how we're doing." I started sucking on her nipples but then paused for a moment and looked up at her. "Now you understand I don't enjoy this, I'm thinking of dick right now."

"You're not even remotely convincing, sissy." She shook her head in disbelief. "Now shut up, get back on my tits and take one for the team."

"Well only because you insist."

...

In the morning Cindy got up before me as she often did. She was in the kitchen cooking breakfast in her underwear but I could see immediately something was wrong. She wasn't wearing any make-up, which was very unusual for her and she looked unhappy. I went up behind her for a hug and kissed her on the neck but she was antsy and squirmed.

"Everything OK?"

"It's fine." It wasn't.

"Hmmm...." I had a sense of what the problem may be.

I put my hand into her panties and found her cock cage was sticky. I scooped up some of her pre-cum on my finger and put it between her lips. She licked it off.

"I think it's time."

"I don't want to," she sulked.

"Pretty sure you're on your sissy period, it's getting very wet down there."

"It's not fair."

I turned off the stove. "Come on, someone needs milking, let's get it over with before I go to work. I'm not leaving you to suffer all day."

I dragged her through to the bedroom and sat her on the end of the bed. At least every couple of weeks she needed a release or else she just got into a progressively worse and worse mood as the sexual frustration built up to more than she could bear.

"But I'll turn into him and I don't want to," she started to tear up in the corners of her eyes. "You've masturbated in your girl clothes, right? You know how bad it makes you feel."

"I know. I know." I stroked her hair. "Come on, let's get it done and you'll be back to your normal self in no time."

I knew exactly how she felt. When I came whilst wearing women's clothes, my perspective altered the instant I ejaculated and I immediately wanted to be out of the clothes. I'd tear off my dress and resolve to throw away all my outfits. Sometimes I'd been close to purging my entire collection on the spot. I often asked Cindy to lock the closet door and keep the key safe when I went for my release. When I was on my sissy period, I generally jacked off in the shower on a weekday before I went to work. I would then be getting into male clothes anyway. The sudden shift in my thoughts was even occasionally useful to help me focus on the day, sometimes I could actually make use of it when I had something important to do. Cindy didn't have that luxury though, she was trying to be a full time girl. The clarity also seemed to hit her a lot harder than it did me.

I got on my knees and unlocked her cage. She sprang up almost instantly in expectation.

"Aaron, I'm going to say something really dumb when you do it. I know I am. Just don't listen to me. Slap me, tie me down, do whatever you have to. Don't listen to my bullshit. Promise me."

"I'll look after you. Nothing to worry about."

I started masturbating her little clitoris between my finger and thumb at the same time as sucking her, trying to get her to come as quickly as possible. She was more than ready and came in my mouth in only a few tens of seconds. I wasn't sure if the hormones should be making her produce less sperm by now, but she delivered a large load. I always enjoyed giving oral, but when I sucked Cindy it was almost non-sexual, it was more like a clinical duty that I wanted to be over as fast as possible. I licked her clean and looked up at her.

Cindy's shoulders slumped and she breathed noticeably heavier than usual. She looked around seeming almost disoriented before looking down. "Aaron, I want to get these implants taken out." Her voice had lowered in pitch. She normally spoke in a highly practiced female voice, but she'd dropped it. This was her natural tone.

"That's not what you really want sweetie. We both know you're not thinking straight right now." I got up and sat beside her and tried to hug her but she pushed me away.

"Can you make an appointment? I'm serious." She was unsmiling and looking frustrated, her usual female mannerisms had vanished. It was as if a man had suddenly possessed her. She'd regressed back to her former self, she was Chris again, but not just that she was the most heterosexual straight version of him who had suddenly found himself in a girl's body. I needed to expunge him, I needed some kind of masculinity exorcist to get the male demon out of the girl I loved, but the only tool I had at my disposal was patience. We'd been through this enough times now that I knew if I waited an hour or so, she'd be fine.

"Lie down, sweetie." I gently guided her on to the bed. I snapped my fingers. "Go limp." The special hypnotic trigger rendered her unable to move and she would lie motionless until I released her. I started to get ready for work and came back to check on her every few minutes. I was never sure when she was in this state if she was genuinely unable to move or if it was just some form of deep role play. I kept moving her limbs occasionally in case she got cramps. The fact that she kept perfectly still even though I knew she was in a very agitated state and not in the mood for play made me wonder if there was something more to her hypnosis than I suspected.

I took a shower and started to get dressed for the office. While I dressed in women's clothing most of the time, I hadn't gone much further with overtly displaying my sissy side at work. I had bright red nails which I always kept pristine and my eyebrows were femininely shaped but apart from that nothing had changed. At my encouragement, Cindy had been pushing me to go further. Co-workers at my office thought I was gay and my nails made a clear statement that I was in some way femme. Realistically I had license to do whatever I wanted when it came to female attire, but change was always difficult and I felt pressure to place some kind of limit on my self expression in a professional setting. Perhaps today was the day for a little more though. I put on a black bra and a white blouse that could almost pass for a man's shirt but it was in a feminine cut and had a little detailing around the collar. I wore my regular suit and a tie over the top. I looked in the mirror to see if the bra was visible. In a certain light perhaps you could see the outline and I had just a small hint of a bosom from my little budding breasts. It was just enough to make me feel anxious, which was exactly the effect I was looking for.

By the time I was done I was ready to see if the girl I loved had returned yet. I went over to her and snapped my fingers. "Wake!" I commanded. Her eyes blinked, she exhaled and sat up. "Are you a little sissy?" I asked tentatively.

She smiled a broad smile and stretched her arms in the air. "No, I'm a big sissy!" That was my girl. I knew she would be back, but I always worried every time I lost her.

"Good girl!" I snapped my fingers and she collapsed back onto the bed and closed her eyes for a few moments. I went in to kiss her and she woke up with my lips pressed against hers.

"You remembered." She put her arms around me.

"New house rule."

She smiled and then sat up again. "I've been thinking while I was lying there. I want to punish him somehow for taking me away from you."

"Punish who?"

"Punish me, when straight male Chris is inside my body. If I can't get rid of him, I'm going to make him pay."

"How do you mean?"

"I want to find a way to force him to be a girl and put him in a situation where he can't do anything about it."

"What you got in mind."

"I was wondering what would happen if I had my sissy period outside, far from the house. Somewhere where it was impossible to change clothes. He couldn't do anything but suffer being a girl until he got home, by which time I'd be back to normal again. I mean what if Chris arrived, say, when I was in the middle of the supermarket or somewhere? Imagine if your brain suddenly snapped into pure male mode when you were wearing a dress and make-up out in public. You'd have to just ride it out. Imagine how humiliated you would feel."

I liked where she was going. "What if you came when you had a dick in your mouth? Do you think you'd be able to finish the blowjob?"

Cindy laughed. "Oh wow. That's pure evil," she said wickedly. "I love it."

"But how would you do it? You can't exactly jack off in a public place."

"Have you never been to a Walmart?"

I rolled my eyes. "Seriously, though."

"I wonder if I could hypnotize myself to cum."