Sissy Friends Forever Ch. 02

"Glad we found a winner."

She collapsed on the bed. "I know what would be five stars."

"What?" I lay down facing her.

"Do me with your cock."

"You know I want to give you whatever you want. If you want me to fuck you, I will fuck you." I had some reticence in my voice and she picked up on my uncertainty.

"but..."

"I'm just having such a good run of feeling girly at the moment and that's the quintessential masculine act. I'm worried it might make me feel like a real man and shift my mental focus into a different space where I just don't want to be."

"That's OK sweetie. I don't want you going alpha on me. That's the last thing I'd want."

"Are you sure?"

"Certain." She kissed me. "If you tried to fuck me with your micro-penis I'd probably not even notice anyway. Can you even get it up? Would I be able to see the difference if you could?" She looked at me derisively and shook her head. "As a man you could only ever leave a woman woefully unfulfilled."

"Good sissy." It turned me on when she questioned my male adequacy and I loved her for doing it.

Cindy rolled on her back and stretched up her arms, beaming a wide smile, before rolling back towards me and hugging me tightly. "But as a woman, you thrill me beyond all imagining."

"You always make me feel like a queen."

She started stroking my ass with a certain provocation."So are you ready to try anal yet? I know you've never done it before."

"Not yet."

"Come on, you'll love it. Give it a chance. Nothing will make you feel more like a woman than being penetrated."

"I'm saving myself."

"What for?"

"My wedding night. I'm a good Catholic sissy. No anal before marriage."

"I'm not sure you understand how Catholicism works."

"I want my innocence taken in a 5-star hotel, with a 5-star dildo by a 6-star girl."

"Do I only get 6 out of 5 stars?" she pouted.

"There's not enough stars to rate you."

Cindy smiled. "When I make an honest girl out of you, I am going to give your tight little behind an experience it will never forget." She started singing. "Like a virgin, touched for the very first time!"

"I love the idea that I've got this whole new world of sexual experience ahead of me. You'll make me feel, shiny and new."

"Only when I get my wedding band." She wiggled her fingers in front of me. "We are living in a material world and I am a material girl."

"In the midnight hour, I will feel your power." I stared lovingly into her eyes and stroked her hair. "Let's not leave getting married much longer. I'm getting desperate to make you mine forever." Cindy squeezed me tightly. "Have you been thinking about what kind of wedding you want?"

"Only since I first laid eyes on you."

"What are we going to do? So obviously you're being the bride and I'm the groom."

She looked at me like I was a moron and tapped me several times on the forehead. "Is there a brain in there somewhere? I thought I was the bimbo. We're doing it as two brides, obviously. You're wearing a long, white flowing bridal dress with white stockings and garters. You're going to have long hair and flawless make-up. You're the girl walking down the aisle with all eyes on her. You're going to be more elegant than you have ever dreamed of and every woman in the church will be jealous of you."

"I don't know how my Mom is going to react to her favorite son wearing a wedding dress."

"I think you should maybe start warming your family up to the idea that you wear girl's clothes now."

"Nah. I don't think so." I grinned. "This is how they're going to find out."

She looked confused for a second, but then got it and started laughing. "Oh my god. This is the way you're coming out to your folks? Seriously? You're going to glide into the church in a wedding dress and make-up with them all staring at you?"

"It will be memorable."

Cindy looked stunned. "That's one way to put it. I wonder if they'll try and stop the wedding."

"First they'll think they're at the wrong wedding. Then it'll slowly dawn on them that it's me." Cindy started staring into space. I wondered if I was going too far. "Is that OK with you?"

"Are you kidding? I was just imagining it and nearly came. This will be the best day of my life."

"That's my only hope. So what are you wearing?"

"I'm going full slut bride. It will be very revealing and very, very pink."

"In my fantasies, when I see you in the church, you are looking outrageously inappropriate."

"I will not disappoint." She cupped her breasts. "These bad girls will be on full display."

"I think the officiating minister is going to faint when he sees you." I licked her nipple and she shuddered with delight. I wondered if she was getting any more sensitive.

"Elouise can be your bridesmaid."

"You don't mind her coming to our wedding?"

"Not at all. I want her there. Now you are firmly in your sissy-zone box I'm not scared of her in the slightest. In fact, I want to show her that I got you and she didn't in the most public way possible." She tapped me on the chest with her fingernail. "You belong to me."

"Oh, I'm your personal possession am I?" I wondered if many men might be intimidated or stifled by a girlfriend who was so jealously possessive of them, but not me, I felt the exact opposite. It made me feel so wanted and loved that I so fully occupied Cindy's thoughts, just as she did mine.

"You'd better believe it sissy," she said without any ambiguity. "You will love, honor and most importantly obey. Well I will be obeying you anyway, I'm already working on a new hypnosis trigger word. As soon at that ring goes on my finger, if you snap and say the word 'obey', I will be compelled to do whatever you want without question."

"That's the most erotic wedding gift someone could ever give."

"That's how much I trust you. Promise me you will abuse your power over me as often and as irresponsibly as possible."

"I'll try." I kissed her. "Do you think they still say 'obey' in wedding vows?"

"Ours sure will."

"Glad to hear it. Objectify me some more. Show me just how much you intend to own me like chattel."

"Hmmm ... maybe instead of giving you a wedding band I will have 'This sissy is property of Cindy' tattooed on your rear."

"I'm not sure the minister is going to let you tattoo my ass over the altar. Maybe I should have a wedding band as well."

"That's no fun. Next you're going to tell me they won't let me suck off the best man while you walk down the aisle."

"I understand that is considered a faux pas."

"Which is why after the public ceremony, we send the guests to the reception and ply them with champagne for half an hour, while the real ceremony takes place... in private."

"Tell me more." I was intrigued.

"Still in our wedding dresses, we hold hands and get on our knees in front of two big men."

"Good start, this is definitely going in the right direction."

"After we have pledged ourselves to each other, we will commit to loving cock, worshiping cock, and being forever addicted to cock."

"Then we each suck off our respective man and exchange the cum with a kiss?"

"Do you know why I love you?"

"Is it my talent with a dildo?"

"That and the fact your mind is just like mine."

"We'll need a third ring to mark the occasion. Engagement ring, wedding ring and ... "

"... cock ring."

I couldn't stop laughing. "Perfect."

"Can I have pink diamonds and pink gold please?"

"Anything you want."

"And maybe dicks engraved on the inside of the band?"

"Of course, but you're explaining it to the jeweler."

"I'll say it's some kind of Elvish from Tolkien."

"This is going to be the most amazing day. I'm not sure what I love more, you're body or your devious sissy brain."

"My brain. Stop having straight male thoughts about my body."

"I'm not, I swear."

"Well, I'll allow it for ten minutes. Got the strength to pound me with one last dildo?"

"One more, then sleep. I've got a big day ahead of me tomorrow."

....

It was now early evening, but I'd spent the whole of Saturday getting ready. My legs were freshly waxed, my nails done that morning, eyebrows threaded and I'd had my make-up professionally applied at a beauty salon just hours before. I was quite hungry as I hadn't eaten anything yet for fear of smudging it. I'd gone a bit further than I usually did, I'd had false eyelashes put in and I was still getting used to the feel of them. I was trying to look as different from myself as I possibly could.

I was wearing a long, elegant evening gown in attention-grabbing red with a split down the side that just teasingly revealed my black stockings as as I walked. I'd spent a long time selecting it, trying on different dresses until I found the one that would help me make the boldest and most feminine impression. The neckline exposed my cleavage and I was wearing a very uncomfortable bra that pushed up the little I had to build something that might catch the eye. To complete the outfit I had my finest wig carefully fitted, with long flowing blonde hair cascading down my back. It looked completely natural.

I glided into the restaurant in my heels, walking like a model, each step carefully metered. I was on the arm of a tall and handsome man. Cindy had insisted I take Matteo on this occasion, she had reasoned that this would send the stronger message that I was a sissy.

The host guided us to the table where Naomi, my first ever girlfriend, was waiting for us with her husband. I hadn't seen her in years, but I recognized her immediately. She was wearing casual clothes and by comparison I was massively over-dressed for the occasion, but that was my intent. My heart raced as we arrived at the table. My sissy exposure was about to begin.

We motioned as if we intended to be seated when Naomi interrupted. "Oh, excuse me, these seats are taken, we're waiting for some friends."

"Your friends are here," I said with a smile. "Naomi, it's me."

"Er, who?" she said with not a glimmer of recognition.

"It's Aaron, from college."

"What?"

"I look a little different now." I had understated the situation by a mile.

She stared at me opened mouthed, in complete disbelief. "Aaron?" she finally said.

"Yeah, it's me alright."

Naomi got up and we hugged, then she stood back and looked at me. "Wow! Erm, when did ... I don't know what to say."

"May we take a seat?"

"Oh, sure. Erm. Please."

I introduced Matteo as my 'boyfriend' and Naomi introduced us to her husband, Colton. He just briefly shook hands with me across the table and nothing more. I couldn't read what he made of me but he seemed completely disinterested, doing only the minimum that was socially acceptable. I had hoped to make an impression on him with my outfit, but he didn't seem to notice. He greeted Matteo more warmly though, with a firm handshake and a smile.

In the corner of my eye I saw Cindy enter the restaurant and start making a fuss. She was dressed conservatively, just in a plain T-shirt and jeans paired with black, knee-length high heeled boots. Her long hair was scraped back and tied in a ponytail and she was wearing her glasses, which she rarely did. This was her attempt at being inconspicuous and trying to avoid attracting attention but she was failing at it. She was busy loudly harassing a waiter, demanding that he seat her right next to us, even though the table was far too big for one. Eventually, it turned out the customer was always right and she pitched up just a few feet away from us, easily able to overhear all of the proceedings.

"So when did, erm," Naomi gestured at me, "all of these changes happen?"

"Some time ago. My feelings about my gender go back to when we were together." I gave Cindy the quickest of glances. Unbeknownst to Naomi, we were playing a game to spice things up and it was about to start. A few days ago I'd been lusting over a new pair of designer shoes but in the end I'd passed on them as I judged I just couldn't justify the price tag. Cindy said she would use all of her store profits to buy them for me, but only if I successfully completed a certain number of challenges this evening. She'd set me some special sissy tasks to complete in front of Naomi that we'd dreamed up together over a bottle of wine. They were the sort of things that sounded good when you were drunk and horny but trying to do them in reality was a whole different ball game. Cindy would be rating me on how I did and it would certainly make the evening a little more entertaining.

"I just want to start by saying how sorry I am for not being a real man to you. I'm so glad you've got the husband you deserve now." I saw Cindy studying a menu but with her index finger prominently raised. My first task had been to apologize to my ex-girlfriend for not being masculine enough. Cindy had heard me complete the challenge and was indicating I'd scored a point.

Naomi was slightly taken aback by my admission. "We had some fun Aaron," she said magnanimously. "There's nothing to regret." She turned to her husband and they shared a look of longing. "It's just I've just found the love of my life now and we are so happy together."

"That's awesome." I squeezed Matteo on the leg to give him a signal. "Well, that makes two of us." He reached over and put his arm around me and we kissed with some passion, a long, lingering kiss. I was two for two. A man kissed in front of my ex-girlfriend was another challenge passed. I reached up and removed the lipstick I had left on his lips with my finger, then turned back to Naomi. Her eyes darted back and forth between the two of us, I didn't think she could believe what she was seeing.

"So what do you do for a living Matteo?" she asked.

"I work in hospitality," he said vaguely. It was sort of true. I expect that was probably his go-to job description in regular company.

"Oh, nice, I'm sure," she said, not bothering to ask any follow-up questions. She wasn't very interested or impressed.

"And yourself?" Matteo inquired out of politeness.

"Oh I'm a homemaker," she said quickly. She then turned to address me specifically. "You know Colton's an airline pilot and he used to be in the Air Force."

As she tried to impress me with his credentials, I suddenly had an epiphany. I was sure her original intent had been to compare her husband to me, to try and show how inferior I was as a man to him and that she had 'upgraded'. However, my arrival in a dress had completely derailed her plan. Now instead she was intent on comparing her husband to my boyfriend, trying to demonstrate his occupation held greater prestige. Matteo had made himself sound something like a bartender and she was keen for me to know that she had the capability to attract a man of higher social status than I did. She didn't even ask me what I did for a living, nor even consider I might earn my own money. She wasn't socialized to expect that, maybe none of her circle of married friends worked. Her core identity was clearly built around her husband's job and she anticipated that mine was too. She was treating me exactly like a rival woman she wanted to outclass. I felt a warm fuzzy feeling inside. I had accomplished something. She didn't see me as a man at all. She saw me as a dependent housewife, just like her.

"Really?" I said, briefly turning to Colton, nodding an acknowledgment. "I bet you have some wild stories to tell. I'll look forward to that."

"He does," said Naomi proudly.

I decided I would play her game. I leaned on Matteo and held his arm, stroking his bicep. "You know in Matteo's job, he has to spend a lot of time working out. He keeps himself in such good shape for me." I lightly ran my fingers down his chest while looking at Naomi and saw her eyes track my hand.

She stared slightly too long at his flawless body. I think she appreciated my man had his charms too and we were even. "Erm, shall we order?" she said eventually.

We all agreed we were ready and I decided to go for another challenge while we were waiting. I put my purse on the table and pulled out a compact mirror and lipstick. I opened up the mirror, held it up in the direction of Naomi and checked my make-up. I slowly and deliberately refreshed the lipstick I had lost to my kiss with Matteo. I was trying to read her expression over the top of the mirror. Her lips were just a fraction parted, her eyebrows lowered and she slightly wrinkled her nose. Was it disgust I was seeing in her? Was it disappointment? Whatever it was, it gave me the thrill of emasculation I craved. I closed the mirror, looked directly at her and just gave her the slightest of pouts as I raised my eyebrows. She broke my stare and glanced away. I felt a little bad at deliberately trying to make her uncomfortable, but not too guilty as she clearly had been attempting to make me feel inferior by showing off her new husband.

After we ordered, Naomi wanted to go to the bathroom and I went with her. As we washed up together I struck up a conversation. "Your husband's really cute." I achieved another point by telling her that, as my large-busted shadow was there to hear it. She had followed us to the bathroom and was pretending to check her make-up in the mirror.

"Thanks. It feels so strange hearing you admire a man like that. I mean you're right, he is cute isn't he?" I nodded in agreement. "When we were together though, I never got any idea at all that you were into guys. Not even a hint." An opportunity had just presented itself. I felt butterflies in my stomach but I worked up my courage. It was now or never.

"What can I say? I love cock now." Cindy never thought I'd figure out how to work that into the conversation nor have the nerve to ever say it to her. I wasn't sure how Naomi was going to respond.

"Well ... OK then!" She touched me on the arm supportively. "I'm pleased you're happy."

I was feeling in the zone and wanted to keep going. "Good job Matteo is so big," I said dreamily. I closed my eyes and bit my lip, pretending I was visualizing him. In reality I was seeing my score racking up, my new shoes were in sight. "I just ache for a man to get deep inside me. Don't you?" I stroked the front of my dress just above my crotch for emphasis. Naomi looked shocked at my performance.

"So are you, you know, all woman down there now?" She indicated between my legs with her finger.

"Oh yeah," I lied. "Well, you remember my manhood don't you? Be honest, it was hardly worth keeping was it?" Cindy started smirking, revealing that she'd been eavesdropping. Naomi glared at her and she rapidly left the bathroom. She couldn't keep a straight face. As much as I was getting off on humiliating myself, as far as Naomi was concerned this conversation was at an end. There was little point continuing it anyway if there was no Cindy around to hear it.

"You look amazing hon," she said to change the subject. "Your dress is incredible. Tell me, how long did it take you to get ready tonight?"

"Oh this little thing?" I gestured at myself "I just threw it on."

"Yeah right!" she laughed. "I mean look at you. You're gorgeous."

"Thanks, you're really sweet."

"I'm such a slob next to you."

"Don't be silly, you're hot as hell." The evening had started with an adversarial tone, but I think I was starting to like Naomi again, as I had once done all those years ago. Maybe she'd gone from ex-girlfriend back to girlfriend again, but of a different kind.

We went back to the table and were surprised to see the previously silent Colton deeply engaged in conversation with Matteo, the two were laughing together. "Hey Naomi," said Colton enthusiastically. "Matteo was just telling me he's from Tuscany."

"No way! We went there on our honeymoon. Small world."

"Beautiful region," said Colton. The two men remained in conversation for the rest of the evening, which was causing me a problem. Cindy had challenged me to flirt with Naomi's husband but as much as I tried, I couldn't attract his attention in the slightest. I tried looking suggestively at him but he didn't respond. I tried breaking into the conversation but it didn't work and he cut me out. I just assumed it must be either out of respect for his wife, perhaps he didn't think I was pretty, or quite likely it was because I was trans. With his wife sitting right there, I wasn't expecting much in any circumstance but I hoped to get just a little flirting out of him. Whatever the reason though, he was completely stone cold to me and didn't want to play at all. This was a tough challenge.