The Whole Nine (West) Yards

Chapter 1 - Caught by Renee

My name is Brandi and this is my story of getting a whole lot more than I bargained for. Eight months ago I was a happily married computer software consultant who worked out of his house, while my beautiful wife of 3 years worked downtown as a manager in one of the many corporate offices. Since both of us worked we enjoyed a very good standard of living and didn't have want for anything.

Since I work from home I am able to explore my fetish of wearing women's clothing. I have had this infatuation ever since I was a little boy, but after my mother found my stash of clothes when I was 15 years old, I let it kind of fall to the wayside, that is until I went away to college where I began to amass my collection once again. Upon graduating from college I went to work for a major software firm and was living on my own where I continued to dress up and wear women's clothes, but never outside my apartment.

After a year of working for this company I realized I could branch out on my own and not only set my own hours but make more money. One of my first customers was a corporation that needed some pretty intricate software, so I spent several months developing what they needed, but also got to present regular updates to their management.

While at their offices I was paired up with one of their lead engineers, Sandy. Sandy is not only beautiful, but also extremely smart. I figured I didn't have a chance with her, but somehow she was attracted to my simple charms and so we started dating. During our times together I realized that even though Sandy was fairly naïve when it came to sex, she was willing to try and do different things.

In fact one weekend when we were going away to a bed and breakfast, I decided to bring along some of my clothes and see what she thought. As usual she was willing to try it, but made it plain to me that she really wasn't turned on by me dressing as a woman. I was a bit disappointed, but decided that I would just keep my fetish a secret from her.

We dated for nearly a year before we finally got married and bought a house. During our courtship Sandy was promoted from lead engineer to a manager position, which required slightly longer work hours. Since I was now working from home, her long work days allowed me to still dress in women's clothes whenever the need arose. Since I seemed to be drawn to dressing up I decided I was going to do it right.

I began by removing all the hair from my body from the neck down. When Sandy asked about this, I stated that I had started swimming again and that this is what I did in high school to help. She seemed to accept that explanation, though she gave me a peculiar look. I then went on line and determined my facial tones and features and began acquiring the proper cosmetics.

I bought concealer, blush, mascara, eye liner, eye shadow and lipstick in not only slutty colors but also business appropriate colors. I also started to let my hair grow out some. When Sandy asked if my long hair would impact my swimming I told her I always wear a swim cap so it didn't matter.

With my complete set of makeup I began to practice every day on applying and then getting dressed up for work. Being dressed en femme I sat to use the toilet and made myself drink lots of water so I would have to go often. After doing this for several months I decided to expand my wardrobe and get nice business attire.

I got matching bra and thong panty sets, camisoles, slips, blouse and skirt outfits and dresses. I even expanded my shoe collection, though I only bought heels above 3". I also decided to purchase a set of realistic breast forms. I just loved the feel of them jiggling as I walked. My toy collection was somewhat limited, and so I decided to pick up a butt plug, a suction dildo, a dildo gag, a ring gag and some handcuffs.

After working on a big project I would reward myself by putting on my sluttiest red lipstick and then practicing deep throating the suction dildo to see how far down the shaft I could put lipstick rings. I also began wearing the butt plug on a regular basis as I found it helped me sway my hips when I walked.

After 3 months of dressing for work, I felt very confident in my ability to dress and look like a woman so much that I no longer kept the blinds down in our house. One day dressed in a new blouse skirt outfit, as I was using the bathroom I didn't hear my wife enter the house. In fact I was so caught up in myself that I didn't even realize she was standing in the doorway until I stood up to pull up my pantyhose.

I was quite startled by her appearance and the stern look on her face told me I was in serious trouble. She merely turned around and headed to the kitchen. I finished in the bathroom and quickly followed her. She was sitting at the kitchen table and as I walked up, opened my mouth to begin explaining, but she cut me off.

After what seemed like an eternity she told me that our neighbor Renee had seen a woman in our house that did not look like Sandy. Initially she figured Renee had been mistaken but when she mentioned it again she figured she better investigate things. Imagine her shock and surprise to find out that the "woman" was her husband.

I just about fell over when she told me to show her all of my female stuff. I couldn't believe she wasn't more upset. I couldn't believe she wasn't going to yell at me. Little did I know just how mad she truly was. She sat on the bed and watched as I pulled out dozens of outfits, to include shoes.

Looking at all my female items, she asked if that was it and I started to say yes, but when she looked at the drawer where I kept my toys I realized just how much trouble I was in. As I pulled out the different items, she held them up and looked at them. When she got to the dildo she noticed lipstick on it and compared the color of the marks to the lipstick in my makeup bag and just made a disgusted noise as she tossed the dildo on the bed.

Sandy then began to explain to me the dire situation I was in and that in order for her not to divorce me and take everything I owned I had better comply. Realizing she was extremely upset I readily agreed to do whatever she said. She told me she thought I would say that and proceeded to call someone.

All I heard was her tell someone that I had agreed and to come over. I didn't have to wonder long who it was as I heard our back door open and I heard Renee's voice call out. Sandy told her we were in the bedroom. As Renee came in she walked over to me and told Sandy that this was the woman she saw through the windows.

She then told me that I looked pretty good. As the girls went through my clothes I couldn't even begin to imagine what they had in store for me. Sandy handed me a racy outfit which consisted of my short leather skirt, red low cut blouse, red garter belt, black nylons and my CFM platform red heels and told me to change. I went to leave the bedroom and Sandy asked me where I was going.

She said, "We're all girls here, what do you have to hide", so I stripped down and changed there. As I removed my pantyhose Renee noticed the butt plug and came up behind me and gave it a jiggle. Unfortunately, for me, my cock gave a twitch when she did that, which did not go unnoticed by Sandy. Sandy then asked if I had any glue for my breast inserts and when I told her I did she instructed me to make sure I secured my breasts so that they wouldn't come off. When I looked at her incredulously she stated that since I wanted to dress as a girl she was going to let me be a girl.

After I got dressed, the girls watched me put on my make up giving me suggestions on how to look more seductive. Sandy explain that Renee and her husband, who were part of the local swingers club, were going to come over for dinner and that Renee was going to explain to her husband that I was a friend of Sandy's from work who had gotten divorced and that I had not had sex in a really long time and needed some cock.

Unfortunately, I was only going to be able to give oral as my monthly visitor had just arrived. As I stared at Sandy in shock, she merely indicated my lipstick ringed dildo and told me that I should have no problems. Renee, then left to get ready, while Sandy sat and drank wine while I prepared our meal. As I finished setting the table for dinner, Sandy told me to go and freshen up before our guests arrived.

While I fixed my makeup in the mirror I couldn't believe where this was headed. As I entered the living room Sandy handed me a glass of wine and told me not to disappoint her or I would be sorry. I took a big swallow of wine and told her I would do my best. Jim and Renee arrived shortly and I could tell that Renee had filled Jim in as he was overly affectionate towards me when we shook hands. Sandy then suggested we sit on the couch and chat while we waited for dinner to be ready.

Dinner was already ready, but I figured this allowed Jim more time to flirt with me. Sandy had me sit on one end of the couch with Jim next to me and Renee next to him. As Renee and Sandy chatted, Jim chatted me up, along with rubbing his leg against mine. I tried to look happy, but I must have looked nervous because at one point Renee told me to come with her to the little girl's room.

As I followed Renee into the bathroom, she turned around and told me that I needed to relax and act like I wanted to get hot and heavy with Jim. I just looked at her blankly and didn't know what to say. She then reached beneath my skirt and began to play with my cock. As I squirmed she told me that I could either let her finish or she could leave me semi hard and we could go back out.

Seeing as how I didn't want Jim to know I was a guy I hiked up my skirt to grant her better access. She reached behind and began to slide the butt plug in and out while stroking me. This stimulation along with Renee licking my ear caused me to blow my load rather quickly and all over her hand. She then proceeded to feed me my own cum and tell me that I should have no reason why I can't be more playful now.

As we exit the bathroom, Jim can see that Renee's lipstick is smudged and smiles to himself. At that moment Sandy announces that dinner is ready. As we sit at the table Jim holds my chair out for all three of us 'girls' and then sits down between his wife and me.

Once seated he immediately puts his hand on my leg and begins stroking it. I reach over with my foot and begin to play footsie with him. He takes this as a good sign and works his hand up higher up my leg. I'm afraid he might touch my flaccid cock and so I reach down with my hand and direct him lower. Thankfully he takes the hint, but not before he grabs my ass.

The rest of dinner goes by without too much excitement and thankfully the wine is flowing freely as I am sure I will need all the liquid courage I can get. As everyone pushes back from the table, Sandy suggests we sit out on the deck and enjoy the evening.

Renee tells Sandy that she just saw a new recipe for a quick dessert and says that she will help her make it while Jim and I go out and enjoy the cool night air. As Jim leads me out onto the deck, he quickly puts his hand on my ass and directs me to a love seat out of the way.

When we reach it, he turns me to face him and leans in for a kiss. I am taken aback and gasp. This only allows him to close the gap and slip his tongue in my mouth. At first I don't respond but while he is squeezing my ass he begins to reach up to my breast and so in a panic I begin to kiss him back. At first it feels awkward to be kissing another guy, but as I feel his strength encircle me I feel myself let go and just fall into his embrace.

After what seems like an hour he breaks the kiss and asks if I can help him release some stress. I give him a quizzical look, but he merely places his hands on my shoulders and gently pushes down. It then dawns on me what he is talking about and before I know it I am kneeling before him and am staring right at his bulge.

I continue to stare and hear him tell me that it's okay, and that Renee won't mind. In a daze I reach up and begin to unbuckle his belt and undo his jeans, as I slide them down his legs his bulge becomes even more pronounced and I can't help but lick my lips. He sees this and says, "let me help you" and hooks his thumbs in the waistband of his underwear and slides them down his legs.

I am now staring at a rather large penis. One that is not only standing erect but also leaking pre-cum. Again, I unconsciously lick my lips and I hear Jim to tell me to kiss it. As I reach my nail covered hand to hold it I lean in and give the tip a brief kiss. I pull back and a drop of pre-cum creates a string that connects my lips to his dick.

As if I am having an out of body experience I watch myself lean forward and lick the tip of his cock and swirl his pre-cum around on my lips. As I hear him moan my inner woman takes over and I take the tip of his cock into my mouth and begin to lick it and I stroke his shaft with my hand.

I take more and more of him into my mouth and feel him reach down with his hands and help me along. As my nose touches his stomach, I kneel there and hold his cock in my mouth and throat and savor the feeling. I then begin to slide back and forth on his hard-on while I tease the underside of his balls with my nails. It isn't long before I begin to feel his member swell and as he releases his load, he holds my head in place so that it shoots down my throat. Half way through he pulls out a little and allows my mouth to fill with his hot, salty load.

I realize a little too late what he is doing and before I can swallow my mouthful, some of it escapes my lips and oozes down my chin. He finally subsides and as he removes his semi hard cock from my mouth he thanks me for a wonderful blow job. I hear the back door open and quickly stand up and start to smooth my skirt when out walks Renee with Sandy behind her with a tray of drinks.

Renee comes right up to me and wipes Jim's cum off my chin and sticks her finger in my mouth and whispers to me that I should try to clean myself up in the future. Blushing I turn from her and go to sit down, I expect Sandy to sit next to me but Renee does instead.

As we sit sipping out drinks I notice Jim is now putting the moves on Sandy and am about to say something when I feel Renee's hand slide up my leg and begin to stroke it. Maybe it's because I just gave another guy a blow job, maybe it's because of all the wine and maybe it's because I am really starting to explore my own sexuality, but I just sit there and look at Renee.

Upon seeing my accepting look in my eyes, she leans in and begins kissing me. I don't hesitate at all this time and passionately kiss her back. The feeling of our lipstick covered lips sliding around feels delicious. As we separate I glance over and see Jim and Sandy going at it hot and heavy.

They are kissing, with Jim feeling Sandy up and Sandy rubbing his crotch trying to revive his monster. As Jim pinches her nipple, Sandy moans and my cock actually twitches. Renee then stands up, pulls me with her and leads me back inside to our guest bedroom. As we enter, she turns around to face me and while we are kissing, begins to remove first my top and then hers. As I look down I can see that her bra has slits where her very erect nipples are poking through.

I quickly lean down and begin to flick my tongue over them causing her to pull my head to her chest and moan. After several minutes of this she puts her hands on my shoulders and pushes me down. As I hike up her skirt I am suddenly hit in the face by a strap on dildo.

For the second time tonight there I am, on my knees, face to face with a cock. As I pause to get my bearings, Renee tells me that she knows I'm good at sucking cock because she and Sandy could hear Jim's moans earlier. She tells me to get her 'cock' nice and wet because she is going to use it. What she says sinks in and I begin to lick and suck on her phallus trying to make it as wet as possible.

After five minutes or so she tells me to get on all fours on the bed. Once there, she rucks my skirt up around my waist, grabs my butt plug and gives it a tug, smoothly removing it. The feeling of emptiness of not being filled is short lived as Renee quickly slides her strap on in my ass.

Soon her hose covered thighs rub against mine and she merely stands there and rocks back and forth so I can feel the entire cock up my ass. As I let out a low moan, I find myself pushing back as if to get more inside of me. Just as I am enjoying the feeling of her strap on inside of me she begins to withdraw it slowly, but then slams it all the way back in quickly.

After several of these she sets up a rhythm and is earnestly fucking me. The feeling is incredible and before I know what is happening I am erupting all over the bedspread and Renee is collapsing on top of me. As she unbuckles the strap on, leaving it inside of me, she crawls onto the bed and feeds me my cum. She looks at me and knows I have been broken and can't wait to tell Sandy all about it.

Meanwhile Sandy and Jim are getting busy themselves. After we left, Sandy stood and unbuttoned her dress letting it drop to the deck. She is standing there in a matching, lacy demi cup bra and garter belt with no panties. Jim wastes no time sliding a finger inside her while he leans in and takes one of her nipples between his teeth. He pulls on her nipple and strokes her love button, while Sandy starts to hump his hand.

Figuring she is ready Jim stands up, bends her over, drops his pants and underwear and prepares to mount her. He places the head of his cock at her very hot and very hungry opening and teases her by holding back. It's not until she is furiously wiggling, trying to impale herself on him that he fills her completely.

As he pulls her onto his cock, she lets out a loud moan. He then proceeds to slowly fuck her causing her to have multiple orgasms. When she thinks she can't take anymore he picks up the pace and before long is pumping his cum deep inside of her. Just as he softens and slides out of her, Renee appears and asks if he is ready to go home.

Sandy still spent from her fucking by Jim is still bent over. Jim leans down, gives her a kiss and tells her that he would love to do that again. Renee also leans down and gives her a kiss and whispers that she broke me.

Sandy stands up and comes into the guest bedroom where I am still laying on the bed. As she climbs on, she straddles my face and tells me to clean her up. I am still in a daze from being taken by Renee and just start licking her well used pussy.

She starts to flex her Kegel muscles and forces Jim's load into my mouth. As I wonder about the new taste she explains that things are definitely going to change around here. To begin with, I am to move all of my female items into the guest bedroom as that is where I will be staying from now on and that I had better get used to tonight's activities because there is going to be a whole lot more of that.

Chapter 2 - The Next Day

The next day as I slowly wake, all of last night's activities come flooding back to me. As I lay there in our spare bedroom I realize in a very short time I went from a frequent crossdresser to a cuckold sissy. Sandy walks in and tells me to get up, get cleaned up and that she has laid out my outfit for the day. As I throw back the covers Sandy sees Renee's strap on laying on the bed and tells me to make sure I clean my toys after I play with them.

Embarrassed I take the strap on with me and head to the bathroom. As I strip off my clothes Sandy walks in and tells me to step in the bathtub. Once there she begins to apply a foul smelling cream all over my body from the neck down, to include my balls and ass crack. I know that this was some sort of depilation, but that didn't cause it to burn any less.