New Pink Panties - Part 2 (cuck, cd, bi)
The following day, after Jaylen left, an awkward silence fell between Wendy and me. I had showered, washing off the makeup and other stains of the night before. When I stepped out of the shower, Wendy was gathering up the lingerie I had worn the night before, tossing it in a mesh bag with her own to throw in the laundry. In the light of day it all felt very strange.
I made an excuse to go out and run some errands, and when I came back home, my bra, panties, and garter belt were arranged neatly on top of my chest of drawers.
"You need new stockings." Wendy said, walking up behind me. "I had to throw the ones from last night away, too many runs. Let's go shopping, to a store this time. I think it's time we get you a dress."
We drove to the mall, pulling up at Wendy's favorite department store. She had measured me beforehand, and gathered a few skirts and dresses which she discreetly passed to me at the men's dressing room. Every time I opened the door, my heart pounded at the thought of a clerk catching us, but the store was nearly empty that Sunday afternoon. We left the store with three dresses and a few extra pairs of stockings.
Wearing lingerie in our house was one thing, but it was clear that she now wanted to take me out "in public." She wasn't quite ready to tell me where just yet. We drove home, and we spent the rest of the evening trying on different combinations of dresses, makeup, and lingerie, until she was satisfied with how a few of them looked.
It did not take long to find out her plans. The following Friday when I got home from work I walked in to an empty house. Wendy was usually there; she always had Friday afternoons off and was usually home. She had not mentioned anything to me earlier that day about being out. I assumed she was out running errands. That was until I went upstairs to our bedroom to change.
On the bed was one of my new dresses, some lingerie, and a new pair of black pumps that she must have bought earlier in the day. There was a note from Wendy the address to a club on the other side of town, with instructions to meet her there at 10. She was leaving me to dress myself, and go out for the first time on my own. At the bottom of the note, she had written, "Wear your cage, I don't want you getting hard at the wrong moment. And your name for tonight is Samantha."
I had gotten hard just seeing the things on the bed, and the note just made it worse. I hopped in the shower to freshen up and shave myself smooth. I jacked off after shaving my pubes, and came quickly, preparing myself like that had pushed me to the limit.
Dressing took forever, especially the makeup without Wendy there to help. It was good I had started early. It slowly came together though, and by the time I slipped into my dress, the degree of transformation was shocking even to me. I looked in the mirror, and Samantha, tonight a brunette, looked back. In the bright light of the dressing mirror, I would still fool no one, but in a dark, smoky club, it might just pass for a while.
I looked up the club she had chosen online before leaving, it was listed as a gay club, but the reviews indicated it now drew a mixed crowd, drawing a large crowd of students from the nearby all black college. What the hell was she up to?
When I got in my car, I quickly realized that I was not quite ready to drive in heels. I kicked them off and drove barefoot. The thought came to me that I would have to dance in them tonight as well, and dancing had never been my strong suit, even in "normal" shoes.
After parking, as close to the door as I could, I realized that I did not have a purse. I had tossed my wallet onto the seat beside me, not that I had any place to put it now. I pulled a couple twenties out of my wallet and tucked them inside my bra. I summoned what courage I could, then stepped out in public as a woman for the first time.
I had no idea what to expect, but the bouncer at a gay bar has probably seen everything, and paid me little attention. There was no cover for ladies, a nice advantage of my current "state." Inside was dark and smoky, as I had hoped. Once inside, I texted Wendy, as she had asked. I had expected her to meet me inside, but could not see her on the dance floor.
A minute or so later, I received a reply from Wendy's phone. It had not been sent by her, because the photo attachment that came with it showed her on her back, legs wrapped around a black man I did not recognize, getting fucked. The text said simply "Have fun, she will pick you up when she's done. Don't leave."
I looked around, confused at the change in plans, and felt a pang of anxiety about being alone. I almost lost my nerve and walked out, but someone tapped me on my shoulder. I turned to see what was obviously another crossdresser, white and probably in his early forties.
"Samantha?" He, or she, or whatever, asked.
"Yes." I answered, trying to soften my voice as much as possible. My mouth had gone suddenly dry.
"I'm Amanda. Wendy told me to meet you here, she thought I might be able to help you out a little."
Amanda was a little shorter and thinner than me, and was wearing a red mini dress, white stockings, and red pumps. What caught my attention were the full lips and bright red lipstick. Amanda had had plastic surgery, and I caught myself wondering if "her" breasts were merely forms or if they were implants. My cock tried to stiffen in its cage, but the rigid plastic did its job and suppressed my erection.
I took the drink, sipped it to moisten my lips before answering. "Help me out with what? She didn't really mention any of this."
"This is your first time in public isn't it?"
I nodded.
"I was terrified my first time, even with my wife with me. It's a big change, one you can't possibly understand yet."
"How do you know Wendy?"
"My wife Becky is with her tonight, she and Mike have been lovers for a while now. They're the reason I've become Amanda. Mike had been fucking her for about a year before he convinced me to do it. Things had gotten tense at home, I thought Becky was falling in love with him, and I started to get jealous. He thought it would make things easier for me, help me become more submissive, if I were to become more feminine. It looks like you are off to a good start. How did you start?"
I told him about the time he had given me Wendy's stockings to wear, and of how my crossdressing had grown since, finishing with the story of going all in the previous week and letting Mike fuck me.
"It's easier to deal with now isn't it? I know Becky is getting fucked right now, but I'm happy for her. I don't even need to watch any more, I have my own thing now."
One
"What do you mean?"
"Everyone needs sex, but can you really go back to women at this point, even if your wife wanted you? She's getting everything she needs from Mike and her other guys. At least this way you get a little taste too."
I had no idea how to answer, but he was right, it had been a long time since I had imagined fucking Wendy, but I now thought about having another cock in my ass all the time.
Amanda, she still hadn't told me her real name, glanced down at her phone. "If you want to stick around, a couple of guys are coming here to meet us in a few minutes, and if everyone hits it off I have a hotel room a couple blocks away. I've been with both before, so the three of us will be OK if you are not ready for this yet."
I thought for a moment, then answered, "I need another drink first, but yeah, let's see what happens." When Joel and Rob arrived, everything happened very fast.
Two hours later I was being led through the lobby of a budget hotel, holding hands with Joel. Amanda and Rob followed along behind. My head was buzzing a little from the drinks, but I was fully aware of what was happening. I had been dancing for the past hour alternately with the two of them, and had learned enough about them to feel safe. They were lovers, but enjoyed sissy bois. They had met Amanda a few months back at the club, and had shared her several times. They were eager for a foursome, and I must have met their expectations. They were clearly there just for the sex, and had shown little interest in chit chat. They happily agreed to move on to the hotel the second Amanda suggested it.
Once in the room, we found our way to a bed, Amanda and Rob taking the other. Joel was gentler than Mike had been, exploring my body as he would have a woman, slipping off my skirt and sliding his hands up and down my stockings, taking his time.
I reached for his crotch, feeling the hard cock that had been pressing against me as we danced, and unzipped his pants, freeing it from his clothes.
I slid down in the bed, taking him in my mouth, and savored the taste of his cock. He was a little smaller than Mike, and I was able to deep throat him easily, quickly making him slick with my saliva. I glanced over to see Amanda, now on her knees next to the bed, sucking Rob with deep, sloppy strokes. Her dress and panties lay in a puddle under her knees, and I could just make out the pink chastity cage on her cock.
I returned my attentions to Joel, teasing his cock with my tongue from time to time between taking him in my throat. Before long I felt Robs hands on my hips, pulling me towards the edge of the bed. He slipped my skirt up over my hips, and then pulled my panties to the side. He slipped a lube slicked finger into my ass, working it in and out a few times before adding a second finger. He probed me several times before removing his hand. I heard him tear open and slip on a condom, and forced myself to relax as I felt his shaft probe against my anus.
Amanda slid onto the bed next to Joel, now down to just her bra, garter belt and stockings. I could see now that she had real breasts, not forms. They were small, probably B cup, but she had clearly been taking hormones to make this conversion. There was no hair on her body, and I was immediately jealous of her looks.
I didn't have long to revel in my jealousy, for Rob finally entered me, pushing a little at a time until he had his length inside of me. He felt larger than Joel, nearly as big as Mike, but I took him without any pain. I found myself once again at the center of attention of two men, feeling full. We fucked that way for several minutes, but I soon lost the ability to focus on Joel. Amanda eagerly took over for me, and Rob rolled me over on my back, pulled my skirt completely off, and resumed fucking me.
From this position I could see my locked cock bouncing back and forth as he fucked me, pre-cum weeping from the tip as it strained against the cage. I felt Amanda brush up against me, and looked over to see her on her hands and knees as Joel began to fuck her from behind. He unsnapped her bra, freeing her breasts to bounce just inches from my face. I took one in my hand, feeling its softness, her smooth skin warm to the touch. She looked over at me and smiled, seemingly understanding that I did not want them so much as I wanted some for myself.
As I played with Amanda's breast, imagining having them myself, I became aware of a new sensation rising in my body. The head of Rob's shaft stroked across my prostate with every thrust, bringing about a sensation I had not experienced with Mike. My body began to shudder, and my cock spasmed. I groaned as I came, dribbling cum through the chastity cage onto my belly. I cried out as I came with an orgasm more intense than any I had experienced before.
Rob began to moan, picking up his pace, and I could tell he was going to cum. He pulled out, slipped off the condom, and motioned for me to get on my knees on the floor. I slipped off the bed, and before I could even look up felt the first of his load spray onto my face, stinging my eye. I opened my mouth, and he slipped his cock in and finished his orgasm in the back of my throat. His taste filled my mouth, and I swallowed when he was finished, then wiped my face clean with my finger, licking it clean with my tongue.
Joel kept fucking Amanda a few minutes longer before blowing his load, deep inside of her, and when he pulled out I could see they had been fucking bareback. I imagined they had clearly been doing this together long enough to have some degree of trust.
I immediately wondered what that would feel like, having someone cum inside of me, but that would have to wait for another night. It was clear that Amanda and I had served our purpose, and Rob and Joel were spent and ready to go home for the night.
Amanda was staying at the hotel, and invited me to stay. She finally let me know that Wendy was at their house with Becky, along with Mike and a few other bulls for the evening, and wanted to have the night to themselves. I decided to go back home, there were things that I was not ready to talk with Amanda about just yet. Rob dropped me off at the club, and I drove home to my empty house.
Wendy texted me a little after midnight, while I was still driving, letting me know she would not be home until the following afternoon. "Hope you had fun!" she wrote, "I know I am!"
I took a quick shower when I got home, then went to my lingerie drawer and fished out my pink lace panties from my first night with Mike. I slipped them on over my cage and crawled in bed. Wendy had the key, and it would be a while before she would be home to let me out. I fell asleep thinking about Amanda's breasts, and whether I was ready to take that next step.