Disappointment

It's been a loving journey these past few months. I am so glad my wife caught me crossdressing, but even more elated that she, with the help of a sex therapist, was able to accept my new feminine side.

Last month we had dinner with my regional supervisor. My wife who is now my Dom required me to wear a woman's blouse and earrings. My regional supervisor did notice, even though the earrings and blouse could easily have been missed. He hinted that he and his wife were also into similar kinks and I suggested he bring his wife to town and we could have dinner together. He seemed to like the idea.

That Monday at work I was a nervous wreck. What would he do when we saw each other again? Would he still respect me? Would I still be in line for a promotion soon? All morning I fretted, getting almost no work done. I was just a nervous wreck.

I expected Terry to be in the office early and working together. We would be working together all week setting the parameters of the next project which I was to head. He didn't show up to my office until almost noon.

I had barely gotten anything done when he finally entered my office. With a short formal greeting he looked over my work. We need more details on the goals, the deliverables, we will present to the clients, was his comment. I just stopped and stared at him for a full second.

I can't set those goals in a vacuum. I need to meet with you and the clients. I need to interview them and determine what it is they actually want. You know I can make up a strategic plan for this project, but if I don't guess right at what the client wants then we'll blow this account. I don't want my first executive level project to flop.

Now it was his turn to pause. He sighed and said, "Let's go out for lunch and plan."

My emotions were all over the place. I'd been nervous all morning wondering what he was thinking. I couldn't concentrate on work. Not that I could do it anyway without the key players being involved. Now he wants to go to lunch. "Fine, let's do lunch."

Lunch was a quiet affair. I don't know what to say and Terry looked like he had something to say but wasn't sure how to start. See therapy was good for something, I could see how he was on the verge of talking, he just needed a bit of a nudge. I reached across the table and touched his hands. Gently cupping them in mine I waited until he looked at me, then said, "Whatever it is you can tell me."

I didn't really expect a break up with my first boyfriend before we even started dating, but that's what happened.

You see, Terry said, "I'm your supervisor. I can't have a relationship with you or your wife because of that."

I was a bit hurt, crushed more like. Terry was so hot, and easy to talk to. I would have loved to learn about guy on guy sex with him. Heck, I didn't even know I was bi or pan or whatever they call it before we met. Now I didn't even get a kiss before losing that.

He was great about it though. He set me up at work with a team and all the resources I would need to succeed. I set about doing that work. I threw myself into the work 12 hours a day and a demand for excellence for all involved.

At home my wife seemed to take the news in stride. She told me that next time he was in town I was to invite him back and not to worry she knew this had nothing to do with me and my crossdressing. I was confused on how she could be so sure, but I loved and trusted her so I accepted it.

With working so much I barely had time to do chores at home and I was afraid my Dom would be disappointed. Instead she did the unexpected and helped with the household chores. The first night when I came home after seven I was frightened that she would be angry. I knew she would have been home for several hours and was probably very hungry and angry.

Instead when I arrived home the dining room was lit with candle light and dinner was ready. In a daze I sat at the table with my wife and we ate a normal meal together that she cooked. I didn't even know she knew how to cook. The meal was delightful and afterwards as I started to clear the table she stood and helped me clean the dishes.

I was in a mild state of panic. Was our whole Dom sub feminization relationship ending? Worse, when we finished she poured me a glass of wine. She directed me to relax then excused herself. I could hear her drawing a bath. Moments later she returned and directed me upstairs where she had drawn a bath for me!

I couldn't help myself. I broke down in tears. "Does this mean you don't want to be my Dom? Am I no longer your little Deserae, your subservient girl?"

Laughing with love she pulled me close and hugged me tight. "Darling, you're still my little slut, whom I love to abuse. It's just that temporarily your job is going to be dominating everything in your life. While you prove yourself to Terry and the executive level. As a caring Dominate I want you to succeed. Therefore I'll do the after care you'll need after being flogged at work all day. In a couple of weeks this project will end and then I'll be happy to teach you new levels of pain and humiliation.

Then she smiled and kissed me.

After a warm and relaxing bubble bath I felt rejuvenated. I took my time and not only washed everything with perfumed soaps, but I shaved every inch of my body below the scalp. Too often when shaving we are rushed and miss those little nooks and crannies. I was so smooth and clean when finished I felt like a new girl. I also smelled wonderful.

Slipping into a sexy nighty I returned to the bedroom. My wife was reading a book and I moved to her side and dropped to my knees. In my submissive pose head down on my knees I thanked my mistress for treating me so well. I begged her for the opportunity to repay her kindness.

If you really wish to please me Deserae you can start by worshiping my feet.

Glad to be allowed to return to my submissive duties I pulled the duvet back to reveal her gorgeous feet. She must have had a pedicure done today because they were so clean and had a sexy yellow nail polish. Looking up I noticed she also had a large strap-on around her waist.

My eyes went wide at the size of the thing. Sure we'd played around with my ass a few times, but never with anything even remotely that huge.

Laughing she said, "Darling you didn't think it was going to be all candlelit dinners and bubble baths did you?"

With a slightly worried grin I began caressing and kissing her freshly painted toes. She moaned with pleasure and every once in a while would attempt to stick her whole foot into my mouth.

She soon tired of this game and ordered me to assume the position. You know the one, ass up and head down on my knees on the bed. Lightly spanking my ass and thighs she teased me. She had gotten a manicure as well and she would occasionally drag those sharp talons across my back. Then up and down my ass and thighs. What at first was a sexy light tease turned into hard smacks on my ass and thighs. I could feel the heat as my ass reddened. Every time she dragged those nails across my now burning ass and thighs it felt like searing lasers tearing through my skin.

Soon muffled yelps could be heard as I attempted to stifle my utterances of pain in the duvet. This only seemed to encourage her as she would laugh and hit me again harder, sometimes with a paddle, sometimes a crop, but mostly with her bare hands.

Finally, I couldn't take it anymore and begged for mercy while crawling away from her across the bed. As I lay there sobbing with pain I soon felt her hands, gentle as the breeze administering ointment and a cold compress soothing my flaming ass.

As the pain subsided I rolled over and into the loving embrace of my wife. Smiling she asked, "Are you ready to get fucked now?"

My fear was palpable as she positioned herself between my legs and brought that huge cock into position. Slapping my balls and then my tender thighs with that monster she laughed an evil cackle. Rubbing that huge penis up and down my ass crack she pushed gently at first, then harder and harder.

I could feel her pushing against my sphincter. There was no way that thing would fit. "Please mistress, can we at least use some lube?" I begged.

Again she laughed and leaned forward to kiss me. "You're such a good girl. Willing to try anything for me, but this cock is too big for you. Don't worry, we'll move up to it eventually, but today we are going to start a bit smaller."

With that she quickly switched out that monster with a more reasonably sized cock. Only 5 or 6 inches long and much, much thinner, though very veiny. Lubing up her cock and my ass she pushed my legs up and back, lifting my ass off the bed just a bit. She slid the tip of her cock between my cheeks and pressed firmly against my sphincter muscle.

She instructed me to spread my ass and let her in. Doing as instructed I reached down and pulled my ass open. She pushed just a bit harder and with a gasp of pain/pleasure I could feel the head slip past my sphincter muscle.

She was inside me. I had lost my anal virginity. Sure it was only the tip and the pain was intense, but it was in there. Slowly the pain subsided and my ass relaxed. She could sense the relaxation and pushed just a hair deeper. Then she pulled back and out.

I could feel my whole body relax as the violation of my rear end had ended. Quickly though she rubbed her thumb across my hole pushing as she went past. Then she grabbed my balls and lifted gently but firmly. With her other hand she guided that cock back against my ass and slipped it back inside.

Further this time. I could feel the veins sliding against my muscle as they went past. Back out again but not all the way this time. Right up to the edge. I could feel my ass tensing as the head of that cock pushed the limits. Then she slid back in. Just a bit farther.

Squirting a bit of warm lube on her cock as she slowly worked in and out of my ass she pushed deeper and deeper. Then she stopped. Leaning all of her weight on me, her baby cock was balls deep in my ass. Every glorious vein deep inside me.

I realized my eyes were closed. I opened them to see my lovely wife gazing down on me. My mouth was open as I moaned with pleasure. When my wife saw me open my eyes she dropped a large wet drop of saliva down her tongue and into my waiting mouth.

I caught her juices then released my legs and legs wrapped around my wifes back. Pulling her close in with my legs I reached up and pulled her face down to mine for a kiss.

A long gentle deep kiss slowly turned into a lip biting and hip rocking fuck. As she leaned back to get more leverage she slammed harder and harder into my ass. She was frenzied. She was biting, licking, kissing, spitting, and slapping me.

I could feel her orgasm building as she leaned farther back, thrusting deeper and harder. She grabbed my cock with her slick lubed hand. Stroking hard with each thrust she was building towards climax."

Cum with me my slut cum with me", she cried.

I didn't need any more encouragement. Bucking like a madman I thrust up with my hips to meet her downwards movement. Neither of us could hold out any longer and in unison we cried out with orgasm.

Normally my cum just shots maybe an inch. Not this time. This time I could taste my juices as they shot all the way up and into my open mouth. Licking the rest of the cum that had left a long line from my chin to my navel she gathered it all up. Then dropped it into my mouth with a deep tongue kiss.

Soon her veiny cock slipped out of my boi pussy, like a real limp dick. We rolled over and held each other for a long time.

Our first fuck as reversed roles was a huge success.