Wheel of Doom

'I should have chosen one of the tight little skirts for you so I could watch that cute butt of yours sway back and forth' she said. That had to be the heels, they made me walk a lot differently than what I normally would. In order to keep from falling on my face I felt like I was walking more on my toes than walking from heel to toe like normal. As she stepped up beside me, she wrapped her arm around my hip, and I drew her close to me by wrapping my arm around hers. I felt great and did not have any nerves whatsoever until we got to the door and saw how packed the bar was.

At this hour I did not expect this many people were still out. Probably because on the walk to the bar the streets were empty. Not a single car passed us by. Now that I was where people would see me, I hesitated.

'You look amazing and have nothing to worry about, I got you' she told me as she pulled me through the door by my hand. While there were a lot of people the noise was minimal. Conversations going on all around us as we made our way to the bar were lively but not so loud that it made people talk too loudly in competition. The music playing in the background also was not so loud that it made people compete with it to be heard. So, the atmosphere was pleasant. We received some glances but no one paid us any real attention from what I saw.

Brenda ordered us a couple of drinks and we found a table in the center of the bar that was vacant. Now to be honest I would have preferred a table in the back, I was nervous.

'Relax babe, you are beautiful and let me assure you, while we were at the bar there were a couple of guys checking you out. If anyone approaches let me do the talking, we have not had any time to practice softening your voice yet.' No sooner had those words left her lips than a well-groomed guy who had to be seven foot tall approached our table. Now I am not physically attracted to guys, but I can see why women would be attracted to this fine specimen! He had sandy colored hair, bright green eyes and a tone build.

'Hi ladies, how's your night going so far?' Ladies? Did I actually fool someone into seeing me as a woman? I felt all warm with that. Brenda smiled at him, and they started chatting. I watched as she talked, watching her mannerisms and how she moved. We learned that his name was Mike and that he was a pharmacist. She introduced herself and then introduced me as Nicky. That made me chuckle. She told him that I was deaf, and she signed what he was saying to me and what she was saying to him. I could have kissed her for that. And boy was I glad that I had learned American Sign Language. As they chatted, she informed him that we were married and appreciated that we caught his attention. Figuring that he was not going to get anywhere with either of us he bade us a good night and went on his way. No one else approached us after he left.

I hope you don't mind that I called you Nicky and told him that we were married, she signed to me. I signed to her that I did not and how much I appreciated her quick thinking. We had not discussed what name to use beforehand and Nicky made things simple since my name was Nick. And telling him we were married stopped any further advances that would have made things difficult. Being called Nicky felt right though. Almost like it was what I should have been called my entire life. Remembering my childhood, I could remember times where I was called Nicky by other kids to be mean but I felt more pleasure than anger every time. We chatted using sign language to keep up appearances and had a couple more drinks. The next thing I knew, it was closing time. Brenda closed out our tab and we walked back to my apartment.

Walking with our arms wrapped around each other's hips as we did on our way to the bar, I could not help but feel ecstatic. My first outing as a woman went without a hitch, I even went to the woman's bathroom and did not feel odd about it. Brenda being with me helped in that regard of course. And I must admit I was a little tipsy too. Opening the door to my apartment I asked if she wanted to come in. I was really wanting to continue where we left off. 'Would you like another glass of wine' I asked holding up the bottle we had started on earlier. She nodded to me that she would, and I poured us a couple of glasses. As I approached her to hand her the glass, I made an impulsive decision and wrapped my free arm around her and drew her close. I lean in and start kissing her tentatively, gently. Passion ignited within me, and I felt it reciprocated as she hugged me tight to her body. Setting our glasses down we continued to kiss. The intensity increased and with what appeared to be a burning need in us both we pawed at each other's clothes to bare ourselves as quickly as possible. We stumble into the bedroom still wrangling with our clothes and fall onto the bed. I kneel by her side and pull her panties off. She sits up and pushes me back and does the same. My cock springs up and she takes me into her mouth. I urged her to swing her leg over my body. I desperately needed to please her as she had done, and was doing, to me. I slide my tongue up and down her vagina, flicking her clit when I got nearby, swirling it. Her moans are muffled as she slides her mouth up and down my shaft. Her hips move guiding my tongue to where she wants it. She partially sits up as my tongue continues its ministrations to her clit. After a few minutes she exclaims that she is about to cum. She dives back down and increases her pace with sucking my penis. A loud but muffled moan emanates from her as she orgasms. She turns around to face me and guides my member inside of her. Sitting up with her hands on my chest she rides me with slow up and down strokes. My breathing is getting faster as I feel my orgasm approach. I start to moan with her, and our pace quickens. I buck up into her, taking control of the rhythm.

'Oh god baby, cum with me.... I am going to cum.... Cum with me...I'm cumming' she cries out. With a moan my orgasm rips from me. She continues to pump me inside of her until my penis stops pulsating and her own orgasm subsides.

Collapsing beside me she lies there caressing my face as I glide my hand across her belly. With the late hour and our physical exertion, we doze off. Waking up a few hours later with my head on her belly I look up at Brenda to see that she is still sleeping. Honestly I am shocked she is still there. I was totally expecting to wake up and find that I dreamed the whole thing. I carefully get out of bed and head into the kitchen to fix some coffee. As the coffee is brewing, I head to the bathroom to get cleaned up. Looking in the mirror, I see that I am a mess. Last night's makeup was completely smeared all over my face and my hair looks like a haystack. I start to pee like I normally would when I hear a sleepy voice say, 'no babe, remember you are a lady now.' That had me jumping out of my skin!

'Yes ma'am!' I replied as I sat down and relieved myself. Finishing I start the shower and let Brenda know that coffee has been started.

'Oh, thank you so much I really need some go-go juice right now.' As I brush out the snarls in my hair, I hear Brenda pour herself a cup of coffee.

As I quickly showered using the shampoo, conditioner and body soap Brenda got me, I reflected on last night. I made it a night as a lady, only a few hours really, so how would I do for an entire day, a week, a month? And holy shit! I made love to the woman I have loved since the beginning of college! That had me fully erect again!

'Alright stop hogging all the hot water' Brenda says as she steps in. 'How are you feeling so far with all this? Besides the obvious' she says looking down at my fully erect penis

'To be honest I'm excited, scared, curious, in shock, never thought anything like this would happen, or that I would do anything like this, and I never thought that I would make love to you. I have loved you, wanted to be yours, for so long.' I told her. And I truly was a jumble of emotions. Like I said I love Brenda, have had a crush on her for years but I always kept our relationship professional while at work and treated her like the best friend she truly was, in our personal relationship because I didn't think she wanted more. I always wanted her to be more than my best friend but was always afraid to ask her out on a date. And the more I thought about what had transpired so far...

I never thought of myself as a guy's guy, didn't like many of the things most guys do. And one thing was certain, I really enjoyed being a gal. This was confusing me since I was brought up conservatively. Guys were guys, and gals were gals, right?

'Understandable, while people for millennia have cross-dressed it's still very much taboo.' She told me with her arms draped on my shoulders. 'I love you too though. Always have and will not let anything bad happen if I can help it. Why though?' I look at her a bit confused, 'why did it take us this long to finally release the sexual tension between us?' We both laughed at that.

'Alright we have a busy day ahead, let's get ourselves put together and get started' Brenda told me as she turns off the water. We towel ourselves dry and start to dress. Brenda pulled out an outfit from one of the bags she brought with her and when she was completely dressed, I could not help but stare. She was wearing a black halter top bodysuit, a pair of short denim shorts that accentuated her curves and a pair of 4-inch-high heels that made her ass look amazing. 'And that look on your face right there is why everyone at the office thinks we're dating.' The look of surprise on my face made her giggle. 'Are you going to finally get dressed or are you going to go to the salon naked?' With a shake of my head to regain my senses (I was absolutely captivated watching her) I started to dress. Once again, the feel of the bra's material had my nipples hard as diamonds and my penis started to grow. As I slid the bikini style briefs up my legs, I was painfully aware that I was fully erect. I really had to concentrate to get my erection to subside enough for me to tuck it between my legs but eventually I managed. I chose a flowy summer dress of a dark blue and a pair of black sandals and sat to do my hair and makeup.

'You know with this being the second time you have put on makeup you sure seem to know exactly what to do. I am really impressed' Brenda said.

'Thanks. I guess all the years of drawing I did as a kid were not a complete waste of time! A lot of the same concepts are used' I told her. My hair on the other hand was another matter.

'Just tie it back, the first place we are going is to the salon to get your hair cut. Pay attention to how they style it. Just like makeup, it is not that difficult if your hair is cut properly. Got to have a good medium to start with which you do.' She said. I had always worn my hair long. And it was all pretty much the same length, about to the middle of my back. A few minutes later we were heading out the door. By the end of the day, I really did not look like the person I was a day ago. My hair was styled. My ears, while having been pierced since I was a rebellious youth with studs, were now adorned with hoops. My nails were painted both on my hands and my toes. And let me tell you that was one experience I wished I had adopted sooner. The whole experience was relaxing, and I was feeling a lot more confident.

'My my my....mmmm mmmm' was all Brenda could say which made me feel that I could really pull this off for the next three months. We left the salon and Brenda commented on how I had an extra spring in my step and a more pronounced swing to my hips. 'You are really enjoying this aren't you' she asked me. I truly was. I felt free. I felt amazing. I felt truly alive. 'I haven't seen you smile this much in all the years I have known you' Brenda remarked.

'I don't know why but I am really happy.' I told her and I couldn't explain it. Something deep inside me was screaming that it was about damn time, and I didn't quite understand why I felt that way. We sat down to have an early dinner and as we ate, we talked about what was to come in the next few months. We chatted like we always had. And as we did, she instructed me on how to soften my voice to make it sound more feminine. By the time we were done I could have sworn that I did not sound like a man anymore. Brenda picked up her phone from the table and turned on her ear buds.

'Listen to this' she said as she handed me the ear buds and pressed play. It was a voicemail I had left her a few days ago letting her know that one of my upcoming court appearance dates had been changed. 'Now listen to this' she switched something on her phone and the sound that played next was of our conversation towards the end of our meal. 'You are a quick study, you do not even sound like you did this morning. Shall we put it to the test?' I was not so certain but said sure why not.

She started typing furiously on her phone and then got up from the table. 'Let's get back to your place and change, we are meeting up with some people tonight. Josh is throwing a party at his place' That spiked my anxiety a bit! Josh is one of the other lawyers that we employed at our firm. As we left the restaurant, she grabbed my hand and we walked out to her car. She must have sensed my trepidation because she said, 'you got this, and I got you, you will do great.'

We pulled into the parking lot of my apartment complex, and I unbuckle my seat belt. 'I'll be back in a couple; I have to go over to my place for some clothes.' Brenda said and blew me a kiss. As she pulled away, I turned to head towards my apartment. Brenda and I both knew that if I am committed to something I will see it completely through. I was starting to wonder though if I was taking this a bit too far. Hell, I was starting to wonder if I wanted to go back to guy clothes at all. Now where did that thought come from? I cannot stay like this forever! Dismissing that line of thought, I entered my apartment and started to put all the clothes I had bought away. As I finished hanging up the last article of clothing, I heard a brief knock and my front door open. 'Nicky, where ya at?' I heard Brenda call; it took me a second to realize she was calling for me. My name is Nick not Nicky, well I guess it's Nicky now that I am presenting myself as a woman.

'In the bedroom, just finished putting away all my new clothes!' She enters the bedroom and deposits a bunch of clothes onto the bed.

'I brought some stuff that I think would look great on you.' As I check out the clothes she brought and start to put them away she holds up a couple of outfits she was contemplating wearing. Choosing one she begins to undress. I was already in the process of getting naked and paused with my dress half off as Brenda started to strip out of her shorts. I could not help but get hard. 'Nicky, while your adoration is flattering, we do need to get ready' Brenda chided me. Once she is completely naked, I decided to take the opportunity to kneel in front of her and give her clit a lick. As my tongue glides between her lips, her hands grasp my head. Her moans tell me that she is enjoying my attention. I continue eating her pussy until she orgasms. She lays back onto my bed and pulls me on top of her pushing my panties down over my ass. 'Just a quick one because we are supposed to be at Josh's house at nine' she says as she guides my cock into her. We slowly gyrate against each other and as I am getting close, I tell her. 'Finish in my mouth Nicky, I want to taste you.' I pulled out of her and stood up. She takes me into her mouth and starts to grip my ass pulling me into her mouth. I feel her hand reach between my legs, and she starts to massage the area under my balls. As she is massaging the area, she slides a finger over my anus. She slowly applies pressure with each pump into her mouth until I feel her finger slip inside me. The feeling was nothing like I had experienced before. She wriggled her finger inside me, and a strange feeling started deep within me. As she massaged my insides further, I felt my need to release more intensely. She fingers me as I am sliding my cock in and out of her mouth. Not able to hold it any longer I let my orgasm loose filling her mouth with my cum.

That was the most intense orgasm I had ever felt. When I let Brenda know, she got this mischievous look on her face. We took a quick shower to refresh ourselves. It was a unique experience trying to shower without getting my hair wet! And I must admit that getting my face ready is taking a heck of a lot less time than the first time I ever applied makeup. So, we were both ready to go in no time. Brenda wore an emerald, green colored corset that zipped up the front, a black ankle length skirt that was slit up to her left thigh but still managed to appear form fitting and a pair of black stiletto heels. I chose a deep blue halter top, a black pleated leather skirt and black stiletto heels. I wished that I had a nice pair of tits like she did so I could wear a corset, they are sexy as hell. When I told Brenda that I was envious she said, 'we could make that a reality.' The way she said that hinted that she was already working on it. But the giggle she let out also made it sound like she was simply kidding. I just raised an eyebrow.

'You look absolutely gorgeous tonight' Brenda tells me.

'Thank you, I owe you big time for this. And you are looking absolutely stunning. What kind of party are we going to? I know Josh is by all appearances pretty conservative.'

'No idea' Brenda replied 'he said that there would be a few people there but no one we would know. All he really said was to come by and have some fun. I didn't tell him anything about you by the way. Just told him I was bringing a friend. I want to see if he recognizes you.' Chatting the rest of the way there helped me practice with keeping my voice more feminine. And Brenda coached me in how to hold my drink and how to sip from the glass that was more feminine than how a guy did it. She said that it is the little things that make a difference. Thinking back and remembering how the guys around me drank their drinks, I have to admit there was a bit of difference. 'The same goes for how we eat. The subtle movements are what separate the sexes. Watch and you will see.'

We pulled into the drive and found a place to park. And as I climb out of the driver's seat and walk around the back of the car Brenda beckons me. 'Turn around really quick' I do as she asks, and her hands slide up the back of my thighs. She pulls my thong off to the side and I feel something hard pressing into my ass. 'Lean forward a bit, spread your legs and relax.' And as I do so the hard object starts to slide in me. I feel like I am being stretched wide, at least it felt really wide, and started to hurt a bit. I let her know it hurts and she eases up. As I start to relax, she begins applying pressure and as I tighten up, she releases pressure. Each time the object is getting deeper and deeper inside me. I inhale quickly as the pain flares up then suddenly subsides. I feel it go in and reach its tipping point to where of its own accord slides inside me and my anus closes around a narrower part of it. 'Mmmmmm now that is sexy' Brenda purrs. It was at that moment that I realized that she inserted a butt plug. She replaces my thong in its proper place and pats my ass. I had to readjust my tuck because that process got me a little worked up. As I was adjusting myself Brenda exited the car. Brenda takes my hand and places it on her ass, with her other hand she grasps my neck and draws me in for a kiss. Gripping her ass, I can feel that one, she isn't wearing any panties and two, she is wearing one too.

I smile a huge smile and say, 'hmm we are feeling awfully naughty tonight, aren't we?'