A Big Surprise!

As a man's sexual desires come to light this story features, femdom, pegging, crossdressing, and dating a TS woman. Please share any constructive criticism or where to take a next chapter. I hope you enjoy!

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My sweet, caring, brilliant girlfriend, Stephanie, and I have been dating for a few months and we decided to plan a long weekend get away. We found a wonderful town filled with great restaurants, microbreweries, and artisan shopping in the mountains. I knew it would be so much fun in town, but I also booked a beautiful Airbnb as this would be the first time we spent the night together.

Since high school my past girlfriends and I were at least fooling around by the second date, if not the first. So when Stephanie asked me to please wait before getting intimate I was taken aback, especially as my love language is physical touch. However, I can truly say that they have been some of the best months I have ever had as we got to know each other so well. I am falling hard for her and I was actually nervous as this is the first time sex was a big step in a relationship for me.

Plus, I have mentioned some of her amazing character traits that truly make her beautiful, but of course you should also know she is an absolute bombshell. Gorgeous from head to toe with black hair, Hershey kiss eyes, ample D-cup breasts, beautiful stomach and long toned legs, nice tight ass, and perfect dainty toes. She was the entire package and I knew she could have anybody in the world so the fact that she was falling in love with me was even more amazing.

On my end, I am told I am handsome, but I think of myself as average. With my full Italian roots I have hair that is a deep black, full brown eyes, olive skin, and a medium build. However, my feelings of being average stem, sadly, from being just average size and thin where it counts. I have learned to make up for my lacking tool with my tongue. My absolute favorite thing is bringing my partner to climax with my tongue and mouth. I say partner as the girl I dated just before Stephanie did lead me to realize some deep kinks I had and also made me realize that though I didn't want to date a guy I did get off thinking about my throat and backside fucked hard.

Our relationship didn't last, but sexually we explored this newly found part of me that only her and my internet searches know about. In doing so she would really take the reigns and dominate me. She started slow with some slight small penis humiliation, mostly commenting about how my whittle penis was so cute, and built that up to sissy role play telling me my little clit needed to cum so hard. As we went down that kinky rabbit hole she began to make me call her Mistress Eve. She would even dress me in a red or black lacey thong she got especially for me and force feed me my cum as she told me good little sissies cleaned themselves up.

I got so turned on by her and was cumming so hard as I enjoyed femdom and being submissive when she ratcheted it up again. She started whispering in my ear about how she would cum harder than she ever has before if she could just watch me suck on a big strong man. She told me how it got her soaking wet thinking of a hard cock down my throat which in turn had me so turned on and wanting to please her. She wanted to know that I really wanted it and wasn't just saying it to get her to cum. The next night to prove it before she could whisper it I emphatically begged for her to find me a big juicy cock. I begged her to help me learn to deep throat so I could properly please the guy she brought home for me. She came so hard so of course it didn't just end there. She knew all along where she was going and led me down the path to pegging me.

She would tell me how I would have to get that big juicy cock as hard and as wet as possible so I could get fucked so hard. She told me how much I would love that big cock stretching my backside and love being filled with hot, gooey cum even more as it would mean my tight boy pussy would have given him so much pleasure. I was so turned on by this fantasy whether horny laying in just my thong talking about it or out to lunch during the week where she would point out other men based on how good she believed they would be sexually for us both. It finally got to the point that she asked if we could really try it. I was nervous, but said yes.

That same night I agreed she got out a strap on dildo she bought that afternoon and began getting me "ready." For weeks she taught me how to deep throat and gave it to me so good in my ass. Whether submissive on my knees or seeing the ecstasy on her face as I laid on my back with my rear end propped up I would cum so hard.

Sadly, I never did get to try the real thing as our sex life was great, but everything else was miserable. After weeks of being pegged we couldn't cover up the problems we had and decided to split up. I did stay a sissy for my mistress until about a month before I met Stephanie. She would text me every once in awhile photos of her wearing the strap on to see if I was busy that night, but that ended when she met someone else.

When we broke up I had not been brave enough to try hooking up with a guy on my own. I didn't know where to begin and it was also clear to me that I don't find men attractive and I never want to date a guy. It is just their cock I want to use them for. So I bought a realistic dildo and kept practicing as it felt so good.

I went on a few dates before meeting Stephanie, but I couldn't bring myself to tell any of my dates and one night stands about this side of me. I had even been keeping it locked away from Stephanie. Leading up to this weekend get away she was excited to hear about any kinky things I loved, but I was so afraid I would scare her away. I felt I could bottle this part of me up if it meant having her love me the rest of my life.

Of course all this added to my nervousness. Would I be a great lover or even a good one in her eyes. Will I be able to please her over and over again. If she finds out about my kinks, especially being dominated wearing panties or wanting to taste cum, will she think less of me and will I lose her. I knew I should be upfront about it and deep down I knew she would accept me, but the anxiety leading up to it was so much to carry.

My sexual appetite and who I was as a person were intertwined and the more I realized this the more nervous I got. This wasn't lost on Stephanie and when we went on a date to a restaurant we both love on the Wednesday leading into the weekend she could tell I was not quite myself. I brushed off her question blaming it on a long day so she decided to have a little fun making me blush.

Stephanie waited until one of our regular waitresses, Allie, was in ear shot and approaching our table as she asked me to bring condoms and to of course pack a lot of lube and any toys I liked. Allie got to the table hearing this and Stephanie turned to Allie to tell her I was going to get anal this weekend, but it was a surprise if I get hers or if she took my sexy rear. This caused me to go beat red, but I was getting so hard under the table. I knew I was lucky enough to have a confident vixen and this was blissfull. I could tell Allie went a little flush and while I was distracted with Allie all of sudden a foot began rubbing my hardening cock under the table.

Stephanie asked, "Allie have you ever pegged a man? Just taking him as yours?"

Allie said she had not, but she quietly admitted to us that was a huge fantasy of hers. She regularly watched videos of a woman taking charge with a strap on and she desperatly wanted to do that.

All Stephanie said was, "Well Allie let me see what adventures this weekend has in store and maybe I will share him to make your fantasy come true."

Now it was Allie's turn to blush and as she stared right into my eyes said, "I would really like that if you are willing. I want to try it so badly and would make you feel so good. Of course that is if Stephanie approves and is there to join in."

Stephanie winked at me and gave a little more pressure as she rubbed my raging hard on as she told Allie she couldn't wait to set this up. As Allie walked away with a huge smile Stephanie then began telling me I was all hers and that she was fully in charge. I had never seen this side of her before and I finished fully falling in love. She told me that this cock she was rubbing was hers, my body was hers, my mouth was hers, and as she said my tight ass was hers I came so hard.

"Oh, so me telling you that your tight ass was mine put you over the edge! Mmm, you are in for an amazing weekend then. I know it has been some long months for you without sex. It means the world to me that you were willing to wait and that I was worth waiting for. I have wanted you since day one, but jumping right into sex didn't work for me in the past and I really liked you so I didn't want to screw this up. However, I am a very kinky sex fiend and can't wait to explore with you all weekend as I know you are too from what you have shared."

As she left her stocking covered toes against me I let her know that I was also very kinky, but didn't want to scare her away. She assured me we would talk about those this weekend and that I could fully trust her to keep loving all parts of me including the sexual kinks I had.

As our dinner arrived there was a wet spot from my cum soaking through my boxer briefs and into my pants, but as I moved to get up to go to the restroom to try to clean a little she sternly told me to sit down. I was to sit in my wet sticky cum and think of her sexy toes painted pink making me explode. It brought me back to the tone Mistress Eve would use to dominate me and I simply was so excited for this weekend!

Dinner was less eventful going forward, yet as always we had such a great time talking, laughing, and being with one another. From when we got up and her foot stopped touching me I seemed to have a constant hard on for the next two days! I couldn't get the excitement for being with her and the desire to be pegged out of my head. That same night I shoved my dildo all the way in, got my legs up over my head, and my cock almost at my mouth. Even after cumming at the restaurant I still came so hard filling my hungry mouth. I slept soundly that night with my head filled with dreams of femdom by Stephanie and could have came again in the morning and multiple times the next two days. However, I was determined to save my cum for Friday night and got more and more painfully horny and needy each passing hour.

Finally the day arrived and while the clock moved so slow it did get to 3pm and I left early to pick up Stephanie. When I got to her door she was absolutely gorgeous. She had on a low cut bright blue blouse with her amazing cleavage on display, tight jeans that accentuated her amazing ass, blue open toed heels, her long flowing black hair perfectly framing her face with a light touch of makeup, and her gorgeous Hershey kiss eyes staring at me filled with lust. I had gone to the door to help her with her luggage, but before I could think my body took over and I pounced on her filled with my own uncontrollable lust. She was up against the wall as I kissed her so passionately, grabbed her hair, kissed her ear lobe and then down her neck. As I grabbed her sexy ass I also grabbed one of her ample breasts for the first time. It felt amazing and as she moaned I couldn't wait to suck on her nipples.

I was ready to slip her low cut blouse over her head when we both regained a sliver of control. As she panted, out of breath and eyes filled with lust, she did gently push me back a step. I too began regaining my breath and I placed my hands on her hips looking into eyes that clearly told me she loved me. Not planned at all as it just came out I told her, "l love you." She teared up, kissed me, and repeated those words back hitting my soul.

After letting this all soak in for a minute or two she did break the trance with a light tap on my arm and a laugh, "Stop standing around and grab my luggage."

We quickly got on the road and I was so excited. Making it even better it reverted back sexual as by the time we hit the highway she had my jeans unbuttoned and unzipped with her hand tracing up and down the outline of my cock in my boxer briefs as she told me about her past sex life. Her's was very limited in comparison to mine and this of course brought up the topic of being submissive and getting pegged. I was really scared to do so, but I told her it all. I admitted to her that I always loved treating my partners to their highest climax as it in turn made me cum my hardest. I also admitted that since Eve my favorite fantasy and sexual thing to do had become to serve my femdom mistress. Through it all Stephanie reassured me that she loved me for me and then shared she had to be the dominate partner yet would do anything I liked in bed, emphasizing anything. As I was debating about sharing how badly I wanted to be force fed a real cock instead of just a strap on we were pulling up to our Airbnb. As I put the car in park I placed a hand on her cheek and began a long kiss.

Though she had been running her fingers and fingernails up and down my throbbing erection the whole drive now at the house she slipped her hand into my boxer briefs and for the first time had her hand wrapped around me. It was incredible and we naturally broke the kiss and as we looked at the lush forest around us we saw that we were the only house around. The house had amazing privacy and we were the only ones staying at the house. Owning these facts Stephanie pulled off her blouse and hopped out of the car.

As she went to walk away she first leaned back in, showcasing her amazing cleavage, Stephanie said, "I hope my red lace bra and clearly hard nipples is enough to distract you so you wait on bringing the luggage in. I will grab the only bag we need. Get your jeans and boxers off."

It was more than enough as I pulled my jeans down, and got my boxers off, and I rushed over to her. I went to hold her hand as we walked toward the house, but instead she grabbed me and pulled me along by my hard cock. I was putty in her hands and ready to serve her every need.

We got to the front door, I punched in the access code, and as we stepped inside I was pushed up against the wall this time. At this point we had so much pent up desire that our hands explored every inch of each other's body. With a big exception, when my hands would began to grab at her inner thighs she would immediately move them. This happened a couple times and then she began to kiss and nibble on my ears whispering in my ear that we had to talk before going further.

"I desperately want you, no, I need you. I need all of you and need to both make love to you and fuck your brains out. We have to talk first though, there is something I have to tell you."

She broke away from our kiss, slipped her hand around my cock again and walked me to the couch. As she centered herself I took a moment to look around and the house was even better in person. I wanted to have her naked in every room and even have her bend me over the railing on the deck facing the woods.

As she sat me down on the couch she look terrified. I grabbed her hand and gently kissed her, "you can tell me anything and nothing you tell me will make me love you less."

She took a deep breath, "I have to tell you two things that I have been keeping from you. I haven't shared yet as I have been so scared of losing you, but please hear me out."

"The first is that I met Eve at a party less than six months ago through some mutual friends. She got quite tipsy and ended up telling me all about her sissy boyfriend, his complete submission to her, and not only what she was saying to him and making him wear she told me what she was doing to him with a strap on. I was crazy turned on as it seemed like the perfect guy for me and as I asked questions she accidently shared how she also had him begging for a cock to please. My jaw dropped as she was just having fun, but I knew I needed someone like that to love me. The thing is I had no idea it was you until about a month into our relationship. It was going so well, I was falling so hard, but I had no idea how to tell you I knew your deepest kinks and that I desperately wanted them with you."

As I stuttered, "wait, you knew about my kinks, my deepest secrets including wanting a cock, and you, you still want me?"

"Not only do I still want you, I need you! I absolutely love it and couldn't wait to explore with you. I just couldn't bring myself to tell you yet because of the second thing you need to know..." As she trailed off I could see tears forming in her eyes.

I leaned in quickly with a kiss and my hand on hers. "You know nearly everything about me, including what I truly feared would make you leave. I love you and nothing you say will make me walk out the door."

She squeezed my hand and just blurted it out, "I am a trans woman."

Not knowing what she meant I told her, "I am not sure I know what that is."

"I am a woman. You see my breasts, my lips, my legs, my personality, and everything about me, but instead of a vagina I was born with a penis. It has since developed into a very large cock. I do mean large as it gets hard it is easily 8 inches long and so fat around." All of sudden she went from explaining to panic, "Please, please, please don't run."

I was silent for a few moments, taking it all in, and between my complete horny body, my love for her, and my deep desire to be a sissy I started to kiss her again, only this time it was deep slow kisses. Moving down her neck I undid her red lace bra letting her amazing breasts fall into my hands. After kissing and sucking on each nipple I placed my head between her breasts pushing them against me as I kissed down her sternum to her sexy abs. I got to her jeans slowly kissed along her waist line as I unbuttoned and unzipped them to see matching red lace panties. As I kissed the top of her panties I slipped my hand in and grabbed her thick, juicy, sexy cock.

As I untucked it I could only stare in amazement. Other than porn I had never seen a huge cock up close, well any other cock up close, and her's was huge. I was filled with the immediate need to taste this huge anaconda. As I sucked it down and it slid to the back of my throat I couldnt believe it was getting even bigger! I could feel it growing bigger and bigger and bigger in my mouth so I took a deep breath and shoved it down my throat all the way to the balls. It was AMAZING!

Her hand moved to the back of my head and after coming up for air she shoved me back down.

"Mmmm yes my cock whore take all of it! Oh my that feels SO good!"

After a few more minutes I tasted her sweet pre cum for the first time. I felt as if I gone to heaven and she had to pull me off of her cock as I just wanted to keep sucking.

"Now you know my deepest secret and have tasted it, it is time I see your secret. I brought a satin thong and a satin nightie for you to wear tonight. I also got you some heels to match that you will wear for me. Let me get them out so you can go change into them. I can't wait for your sexy reveal!"

As she grabbed the two items in crimson red I didn't think it was possible to be even more excited and yet my horny mind had been ratcheted up a notch. As I grabbed them from her they felt so good in my hands. She then pulled out the open toed heels. The heel was so tall I had no idea how I would walk in them, but couldn't wait to try. Finally she grabbed new mascara, blush, and a bright red lip gloss. She told me that she bought those to start having my own make up. She also passed me a razor with vanilla lavender shaving cream and lavender body lotion. She wanted me to shave head to toe, but she needed me too badly to wait so I was instructed to shave my five o'clock shadow, shave all around my sexy little clit, and add some powder to my cheek bones before getting back out here to serve her.