The Valentine Surprise

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She discovers his CD fetish and makes him pay.
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rogkw99
rogkw99
5 Followers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!)

I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Amanda kept promising that she had a big surprise for me. She said it teasingly and somewhat seductively. I tried to act nonchalant about it but I was intrigued and wondered if it were a night of erotic sex. (That made me smile because it had been so long since we had made love) I wondered if it might be a massage for two by candlelight. Or perhaps a concert and dinner out.

Amanda is almost 10 years younger than I and I had been smitten when we first met in college. She was a young vivacious sophomore and I was taking some post graduate courses several years after graduating. It was a chance meeting in a campus coffee shop and a whirlwind romance culminating in marriage 3 years later. We were compatible in almost every way and our union was a happy one for many years. She was attractive and sexy and the sex was good. We did not have children, not by choice but because it just didn't happen. It didn't bother either of us because we were content with our life. I went to work for a large accounting firm and Amanda worked as a paralegal. We both loved to travel and we did so together often.

But time took its toll and almost 30 years later our marriage had become stale. Sex became less and less frequent and we each drifted into our own world. I had a secret I had kept from her from the very beginning. As a teenager, I had fantasies of submission and I experimented with crossdressing. I fantasized about some of my female high school teachers and day dreamed about little scenarios where they would take me home with them and make me do household chores dressed in their panties or lingerie or put me over their knee for a spanking. When I had opportunity I would dress in my mother's or sisters lingerie, or clothing and masturbate.

During four years in the Air Force these fantasies were suppressed as I traveled the world and pursued a very active sex life. Even during the early years of our marriage, the fantasies were suppressed but as the marriage went on, they began to surface and I began to purchase and hide Fem Dom magazines books and videos. I bought female clothing, a little at a time, garter belts, bustiers, bras, stockings, heels, and an occasional dress. I would take these with me when I traveled , spending the entire night in my motel room dressing and fantasizing. I hid my things well and would only dress at home if I knew Amanda was out of town on business. I was extremely cautious since I lived this double life.

Then came the internet and a whole new world was opened to me. I lurked around femdom websites and contacted and visited several professional Dommes, usually in other cities as I traveled. In Washington DC I saw a lady who specialized in transformations and she did a 4 hour session with me, doing my make up and trying several outfits on me, teaching me how to walk gracefully in heels and talk more softly like a lady. Later I bought several wigs. I ran across a website for sissy maids. I was fascinated and surprised to learn that there were a whole lot of other guys who had interests as me and a whole group of both women and men who admired them.

But I digress from the story. As the big day came and I got home from work, Amanda had prepared a nice meal for us. We ate and had a glass of wine. She poured me another glass as well as one for herself and said, "lets sit by the fire and chat". She was wearing a black dress that showed off her legs. She had gotten a little thick in the middle but still had great legs. She suddenly looked straight at me and said, "Rob, I know all about Maid Rochelle". My mind raced and I suddenly felt my face flush. "I don't know what you mean," I blurted out, not sounding very convincing even to myself. "It's your online name on that website you spend so much time on", she went on to explain. I started to deny it again and she stopped me short. "Just shut up and listen!", she ordered. I looked at the floor waiting for the other shoe to drop. "I wondered why you spend so much time on your laptop so when you went on that trip last month, and forgot your laptop, I had my friend Ellen in IT go through it and give me a full report. My, you've been so active and I never would have guessed what you were up to!" I felt as though someone was standing on my chest and it was hard to breathe. She walked over to a drawer, her heels clicking on the hardwood floor and pulled out a folder. She walked back over and began flopping down pictures on the coffee table in front of me. "I had Ellen print these off", she said. There were photos of me dressed as a female, dressed as a maid, pictures of other crossdressers I had chatted with, pictures of professional Mistresses and the ads that I had responded to, copies of emails I had sent and received. It was all there! My throat tightened. "You are actually quite sexy," she said lightly. There was an awkward silence.

Finally, I found myself saying, "I'm sorry you had to find out. So now what? Do you want a divorce?" "Oh, no!" she quickly responded. "That was my first reaction but as I thought about it more and as I delved into the whole sissy maid phenomenon, I think a better solution is for us to enjoy this whole thing together!" My mind was reeling. "What do you mean?" I exclaimed. "I mean you can serve as my sissy maid, silly!" Her voice had a melodious tone and she was clearly enjoying this.

"No!" I said firmly. " It won't happen! It's not the same with you, I couldn't do that with you, you're my wife" I protested. "You can and you will!" she said calmly. "And I can see my life getting a lot easier from here on out", she said. "And if I refuse?" I replied defiantly. "If you refuse, your boss at work as well as your co-workers will get a copy of this folder, not to mention your golf buddies and your poker pals, and maybe even your sister." she said. "You wouldn't! " I protested, jumping up and scooping up all the material she had laid in front of me.

"Oh you can have those." she laughed. "I have lots of other copies. And just in case you get any devious ideas, my friend Ellen kept a set for herself and if anything ever happens to me she will go public with them". I was deflated and defeated and she knew it . "So this was the big Valentine's Day surprise?' I asked. "Well that was just part of it", she said, "There's more!" She reached for her cell phone and dialed a number. "We're ready." she said simply into the phone and hung up. In about 30 seconds there was a knock on the door. Amanda went to the door and opened it. I was dumbfounded as in walked The woman I know as Mistress Victoria, a professional dominant I had visited a few months earlier. "Hello my little Rochelle" she laughed. "Its so good to see you again!"

She was tall and elegant and as she removed her long overcoat she was wearing a black leather bustier with garters that held up silky black stockings and leather boots that came up almost to the knee! Amanda explained that she and Victoria had chatted at length and she thought having Victoria over to demonstrate how submissive I am and how easily I am controlled would be beneficial, all at my expense, she added. Victoria walked over to me and said simply "Strip!" My hesitation was greeted with a resounding slap in the face and I began taking off my shirt. When I was naked she had me kneel and kiss her stilettos. I stole a glance at Amanda. She was seated on the sofa, sipping her wine and enjoying the show. Victoria then told me to go get my feminine wardrobe. I went into the basement and opened the secret compartment I had built into the walk-in closet and retrieved two large suitcases. As I came back into the great room, Victoria commented "You see, I knew he had some things stashed because he brought his fem things to me for our session." Victoria selected a white garter belt, white stockings and white heels with some white thong panties with red ribbons sewn into them. I think you'll look angelic in these" she said. "Now get them on!" Amanda snickered I started to leave the room and she barked, "No, right here slut!" Trembling and embarrassed, I put on the outfit as both women looked on.

Now come over here and sit down" she ordered. "Notice how easily she walks in heels" Victoria observed. She fastened my arms to the chair with straps and then began applying makeup. "We'll not spend too much time on her makeup" Victoria explained to Amanda, "But I want you to see the transformation." Victoria had Amanda leave the room and 15 minutes later she had me stand and face Amanda. "Meet your new sissy maid!" she exclaimed proudly.

Amanda was truly amazed. I was made up with lipstick, eyeshadow, brow pencil and eye liner. She had also put one of my wigs on, a cute short pixie wig with a reddish tint. Now it was Amanda's turn to surprise. As Victoria started to put me into a fancy pink maids dress, Amanda said she had something else for me instead. She went to the closet and pulled out a bag and gave it to me to open. I pulled out a black working maids outfit with a sewn in white apron. "I ordered it out of a uniform supply catalog" she explained. "I think it will be more suited to the actual work Rochelle will be doing" It wasn't lost on me that she was now referring to me as Rochelle rather than Rob. I put the dress on and it fit perfectly. "I think I'll have it shortened a bit though." Amanda explained. "Ill take him, I mean her, to a lady friend I know who does my alterations".

"Now Rochelle, Why don't you serve us some wine?" Amanda asked. I started to fetch the wine and Victoria stopped me. "What do you say Rochelle?" "Yes Ma'am" I said. "And what do you do?" I knew what she wanted. "Yes Ma'am" I said to Amanda, curtseying politely. Amanda clapped her hands excitedly, "Oh precious!" she said. "I want that to happen all the time Rochelle!" "Yes Ma'am" I said curtseying again as I left to get the wine. I returned and served wine to both women who were now both seated on the sofa. "Kneel here in front of us," Victoria said matter of factly. I knelt and the two woman proceed to have a conversation as if I weren't in the room talking about expectations for me, a training program, reward and punishments.

"One more thing",Ms V said. "Rochelle will need to be kept chaste. We can't have your sissy playing with himself or having sex with someone against your wishes," she further explained. "I bought him this little gem. This is a CB6000S chastity device for males. The S is for small." I bristled at this reference to my penis size. I had always been sensitive about it. When erect, I was a full 5 inches but flaccid, it could barely be seen. She brought out an ominous looking device and told me to pull down my panties. She worked my penis into the device and snapped a ring at the bottom of the device around the base of my scrotum. A clear hard curved plastic sheath totally encased my limp penis and could not be removed. I felt a sense of panic as the device was snapped on. " They make metal ones but I like this one because it can pass through metal detectors easily" she explained. "You may eventually get on that is custom fitted to him but it will be expensive. This one was only about $150 and you can send me the money." She clicked a little padlock over a hasp and handed Amanda the key. She explained that I could urinate with it on through a small opening on the end so there was never a need to remove it unless she wanted to have sex with me. "Oh, we'll be having sex alright but all he'll need is his tongue!" Amanda said. Both women laughed heartily. Amanda had always enjoyed receiving oral sex but I was never all that enthused about providing it. I sensed there would be a lot of it now. "I find that when men are sissified, they experience a loss of erections" Victoria explained, "But it's very appropriate for them to service their Mistress orally. If he is not good at it, we can get him lessons." Amanda nodded approval. My face reddened.

"Before I leave, let's explore the finer points of physical punishment. Come here Rochelle and bend over the sofa." Victoria commanded. I complied, the clicking of my heels on the floor the only sound in the room. The big Dominatrix jerked my panties back down. "We'll started with some good old fashioned hand spanking", she said and began slapping my buttocks with an open palm. "Smack, smack, smack! I squirmed but managed to keep silent. "You'll see how his buns are reddening now", Victoria offered, "Here you try now." Amanda approached and began timidly smacking me. Harder! Victoria ordered. The blows became harder and more frequent. I began to moan and squirm. "You'd better calm down missy, or things will get much worse for you!" Victoria warned. I forced myself to silent mode and tried to hold still. Victoria went over the finer points of spanking, how pausing for effect was important and how it should be accompanied with scolding so that it was clearly understood why it was being administered.

Victoria then demonstrated use of a wooden ruler on me and then a hair brush. My buns were on fire and I didn't think I could stand any more. "Now, the grand finale!" Victoria announced. She brought out a leather paddle. "Notice how it has holes in it to make it more effective" Amanda made sounds of approval. "I recommend you get one of these" she told Amanda, "All sissies need physical punishment. You can order then online and I'll send you a few websites for you to browse. You'll find lots of other interesting toys too." She gave me a few swats and I yelped and screamed and tears streamed down my face.

I was allowed to stand erect again and was sent to the corner with my face pressed right into it. "Corner time is a very effective punishment," Victoria explained. "It requires no effort on your part and is tough on your sissy. Every 10 minutes there seems like an hour." The women conversed about my training, do's and dont's and just small talk in general for at least half an hour while I stood there nose pressed against the corner. My legs were straining, my back was aching and my buns were still on fire.

When Victoria left, she had me kneel and kiss her feet and thank both she and Amanda for providing much needed guidance. The ladies hugged and said their goodbyes. "I want a progress report!" Victoria said as she left. Amanda sat on the sofa and had me stand next to her and we chatted about the experience, about her expectations and about how my new life would provide a huge adjustment for me.

I was exhausted and I think she was too. "You may get out of that outfit but leave the panties on", she said. "You'll sleep in the spare bedroom tonight." She kissed me on the cheek and I went to what was from henceforth to by known as "HER" bedroom. "Here, she said" suddenly appearing in the doorway, and tossing me one of her nighties."Put this on and we'll talk more in the morning."

That is how my Valentines day ended. I had a sleepless night between trying to keep any kind of pressure off my sore buns and thinking about the traumatic events of the evening. I still held out hope that this was all a scare tactic and tomorrow things would get back to normal. But now, 11 months later, I can tell you that this was not about to happen. Amanda had me by the gonads and was not about to let go. Her life had just gotten much easier and her status in the marriage greatly elevated. So much has happened since that night that I will have to save it for another time.

Now as Valentine's day approaches this year, Mistress tells me that she has another big surprise for me.

I can tell you that this is worrisome to me after what she pulled last year but what could be worse?

rogkw99
rogkw99
5 Followers
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AnonymousAnonymous9 months ago

Yawn call bs

cdCindy1cdCindy1about 6 years ago
turned me on

This is a bit like what I would love to happen in my marriage. I too am a closet CD and I regularly visit a Mistress. But she doesn't punish me or put me in cockcages. She does help me with make-up. I often dream and fantasize about my wife finding out about my crossdressing and then inviting my Mistress over to our house. She would dress me and do my make-up -- my wife would be so impressed. Then I would serve both of them but no punishment, just serving them orally until they both orgasm into my mouth. They would then both feed me their big strap-on dildos and fuck my man-pussy deep and hard. That would be my fantasy Valentine's Day.

AnonymousAnonymousalmost 8 years ago
Great!

I thought this was a fabulous story. Can't wait to find out what's in store this Valentines day!!

AnonymousAnonymousalmost 8 years ago
Poor story

Forget that I am tired of guys thinking they have to be always humiliated to be feminine as if they ,use have an excuse. Humiliating someone is said not next. But forget that issue. Characters are not developed. Story line rushed. No emotional development of the characters it felt rushed.

AnonymousAnonymousalmost 8 years ago
Really?

This is a porn site. On the world wide web. No one believes a word coming out of your mouth. So just try to write a decent story (this wasn't). And Air Force guy would have taken the ruler away the broken it off in her ass, bitch slapped the wife and divorced her. I guarantee you all he did was take her little finger and break it. He got all copies of the pictures. Even if he didn't his lawyer would have gotten a Court order restraining the wife. She shows anyone a picture, she goes to jail. The rest was unbelievable garbage.

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