Another Crossdresser's First

Wow that was hot!!

I couldn't stop thinking about what just happened. I kept replaying it in my mind. Knelt down in front of a man letting him have his way with my mouth. Submitting to him and feeling him shoot his load in my mouth. I never felt so turned on!!

It was also hot to think my appearance was enough to turn on a man. When I started my journey and never thought I would end up here. My years of practice and research appeared to be worth it.

There were probably two things I had wished were different.

Although I loved the thought of being used for a quickie it was spur of the moment. I couldn't believe I invited him to my house. I wasn't worried about him being discreet but it could have gone differently with another person. This would not happen again.

I was also the initiator although that was probably because it was our first time together. My submissive side wants to be told what to do. I needed to make sure he felt comfortable enough with me that he could express his desires and use me as he sees fit.

The following week I couldn't think straight. I continued to replay the encounter. I found myself daydreaming at work and dreaming about it at night. As the week went on my curiosity kept growing on whether or not he would want to meet up again.

I made sure not to log in during the week. I didn't want to seem desperate even though I was! I made arrangements to make sure my weekend was free in the hopes that I could continue our relationship.

When Saturday arrived I jumped out of bed excited and nervous. I got to work getting ready. I ran a bath so I could fully shave myself. For my outfit I opted for a waist cincher with black seamed stockings, my bra and breast forms, and a dark gray body con dress with some 5" black matte heels. I sat down and applied my makeup finishing with a dark red matte lipstick. After putting on my wig and brushing it out I did a quick check in a full length mirror. I'm sure he would approve!!

I decided to wait until lunch time to log on. There were plenty of taps and chats but nothing from my guy. My heart dropped wondering if he was gone for good. Through out the day I kept checking my account but no luck. It was disappointing and my heart sunk.

Sunday my routine was the same. Some tan stockings, red dress and heels. After getting all dolled up I got online but still no luck. After finishing up some chores and doing my bills I checked online again. And there he was!! He had not hit me up and I decided to wait him out.

Eventually he chatted me up telling me it was good to hear from me again and how much he enjoyed our meet up. He also told me he would love to get together again!! I was so excited and started planning in my mind our next encounter.

As we continued to talk I asked him what he had in mind the next time we met. He played coy and told me whatever I wanted. I needed to get him to open up but he was still a little reserved. I told him how much I loved him fucking my mouth. I also told him I would love for him to take my virginity. Now I have played plenty of times with dildo's but I never had a man inside me anally....yet.

I told him I would love to get a hotel room one town over and invite him up next weekend. I wasn't going to use my home anymore just to be discreet as possible. He told me he had family stuff he was doing the following weekend but that his wife was going to be away two weekends from now. PERFECT!!

We settled on a date two Saturdays from now and he said that he would check in with me the day before. I told him after I selected a couple outfits that he could pick what I wear. He sounded excited at that prospect.

My attention immediately turned toward planning our date. I started making a mental checklist of things to do. Get a hotel room, picking out outfits, prepping myself, and everything else.

Again the start of the week and again my mind elsewhere. Finding a hotel was easy. I made a reservation for the Saturday we agreed upon. I decided I needed to get some jewelry. Despite dressing for so long I never had really used jewelry as part of my outfits. I wanted to give him a good impression. After doing some research I ordered a couple sets of necklaces and earrings that would go well with red, gray, or black dresses. They would arrive in plenty of time.

I wanted my body ready for our date. The last thing I wanted was for him to think he was hurting me or that I wasn't enjoying his cock in my ass. I decided to order a butt plug that I could wear discretely to keep myself ready. I also planned on spending several sessions with my 9" dildo.

The following week my plug and jewelry arrived on time and I decided to take Thursday and Friday off so I wouldn't feel too rushed come the big day. Thursday after getting dressed up, I put the plug in to get used to it for an extended time. I settled on a couple dresses as options for my outfits. I have every color and pattern of pantyhose and stockings so he would have plenty to choose from.

Boy does that plug do wonders!!! I mounted my suction cup dildo and was able to go to town. It wasn't long before I was impaling myself balls deep on it. The dildo was larger than him so I knew I would be ready.

Come Friday I was excited to talk to him and see what he wanted me to wear. I had always fantasized about being dressed in pantyhose and the sensation of having someone lower my pantyhose down or rip a hole in them and fuck me silly. I also loved the thought of wearing stockings with a waist cincher or girdle and having my panties slid out of the way so he could shove his cock in my ass. Either way I was going to love it!!

Later Friday afternoon I got online and noticed he was already on. Good sign!! I sent him a couple pictures of me in the outfits and he picked the red one. He said he loved tan stockings so I quickly told him I had just what he would like. I said I would send the info once checked. He told me he couldn't wait.

I didn't sleep well that night anticipating the next day and was up before the sun. I planned on checking in early as possible to give me time. I packed up all my supplies including lube and condoms. Packed the outfit he selected along with another one just as a backup. After my breast forms, makeup, and jewelry were packed I was all set.

Check in was uneventful. I selected a room on the first floor near a side exit with a king sized bed. I sent him a quick chat with the hotel and room information, finished unpacking, and started a bath to get ready. I had already shaved the previous day so only a touch up was necessary.

I put on my black thong gaff and tucked myself away followed by my waist cincher. My dress is above the knee length so I adjusted the garters so my stocking tops would show when I was seated. I put on the tan stockings and clipped them in place. It never gets old feeling the stockings on my freshly shaved legs.

I've tried all types and sizes of breast forms from plates to glue on. After some experimentation I learned to buy some seamless two-ply cup bras and cut an opening on the outside of each cup big enough to insert the forms. The seamless cups show a little nipple and with the right size bra the forms don't move around.

After putting on my g-cup forms and bra, I followed with my red bodycon dress and sat down to do my makeup. Eyes have always given me a problem but I managed a nice smokey look that went well with my foundation. I finished with some bright red matte lipstick. Its the long lasting kind that is supposed to be blowjob proof!!

I put on my wig and again brushed it out and made some final adjustments. I finished with my red 5" pumps with ankle straps along with my necklace and earrings. I walked over to the bathroom and looked in the mirror. The dress was form fitting and showed my curves off. The waist cincher and breast forms gave me a nice feminine form. The contrast between my tan stockings red pumps was sexy.

At this point it was a waiting game and the excitement and nervousness came back. More excited and less nervous than last time because of my familiarity with him. I checked my phone. He would arrive in just under an hour. I chatted with him and asked if he could bring some beer or wine with him. I needed something to take the edge off. I was hoping it would relax him also.

After about a half hour he told me he was on his way. I told him to let me know when he arrived at the hotel. I cleaned up the bathroom and put all my supplies in the closet. I left the lube and condoms out on the dresser. I knew he would see it and it was my way of letting him know what he could do to me.

Soon after he let me know he had arrived. I used the lock arm on the door frame to leave it slightly open and sat down in one of two chairs at the dining table. I crossed my legs ensuring my stocking tops were showing and waited for his arrival.

He knocked on the door and my heart leapt in my chest. I told him to come in and he did with a bottle of wine in his hand. I could see him looking me up and down with a smile on his face. I also saw him notice the lube and condoms. He said I looked hotter than last time. I invited him over to sit with me and we settled down into some small talk about the weather and other stuff.

After a while I could see him get more relax. I decided to get up and get us a drink. I poured two glasses of wine and went back to the table. I stood next to him as I handed the drink to him. I pulled up on my dress slightly and asked him if he liked what he saw. He put his hand on my calf and stroked my leg up to my thigh. He grabbed my ass and told me again I looked great. That was the first time he had really touched me. Our first encounter he only touched the back of my head so it felt good.

But I was determined not to make the first move. I wanted to make sure he knew he was in charge. I sat back down and we continued to chat over our drinks. The conversation was relaxed and soon he got us refills. I was starting to wonder when he would make his move. You could cut the tension with a knife.

He finally brought the discussion back to our last hook up. Commenting on my oral skills and how it was the best blowjob that he had in forever. I knew he was getting close to propositioning me. Finally he asked if we could do what we did last time. I didn't want him hinting at it or asking me. I wanted him to tell me what to do.

I finally asked him what he wanted me to do. He told me he wanted me to suck his cock. It was such a turn on to hear him tell me that. I told him that I would love to!! I uncrossed my legs and spread them open and reached for his hand. He got up and undid his pants. I rubbed his hardening cock through his underwear. I could see the precum stains and my mouth starting watering. He pulled his underwear down and pulled out his cock.

I slid his underwear all the way down and pulled him close. He guided his cock into my mouth as I started bobbing and licking up and down his shaft. His hands went to my nyloned legs and I grabbed his cock and started to stroke it as sucked him off. He was much more aggressive rubbing my legs and breasts as I serviced him. He quickly grabbed the back of my head and encouraged me to take him deeper.

We kept this up for what seemed like forever. The wine appeared to be doing its job as he was much more vocal saying things like "oh fuck yea" and "suck that cock". It only made me more hungry for his cock.

I know I had made my interest in getting fucked from behind in our previous conversations so in the back of my head (no pun intended) I was wondering if he would finish in my mouth or would he try other things.

Eventually he pulled his cock from my mouth and said he needed to fuck me. I could sense his excitement as he quickly grabbed a condom and slid it on. As he was doing this I stood up and bent over the table and placed my elbows on the table. I didn't hike my dress or adjust my gaff. I was waiting for him.

He lifted up my dress and I was in heaven. He reached down and slid my thong out of the way as he slapped his cock on my ass. I heard him lather his cock with the lube and shortly after he started to mount me.

My previous prep for this worked as he was able to slide his cock in my ass without much discomfort. I couldn't believe this was happening. Here I am bent over a table in stockings and heels getting fucked from behind.

His hands were on my waist as he fucked me. I told him fuck my ass as I pushed back on his cock letting him know I needed it harder. He picked up the pace and started slamming it into me. I was in ecstasy feeling him pound me from behind with my breasts swinging back and forth with the rhythm.

He took his hands off my waists and gripped my breasts as he kept up his pace. I was amazed at his endurance. He also continued to get more vocal telling me to fuck that cock and I again I felt so feminine.

He suddenly pulled out and told me to get on the bed. I did as I was told and got on all fours. He climbed on the bed and using his hands grabbed my ankles and spread my legs wider. This time when he entered there was no resistance.

He quickly picked up his pace without prompting slamming his cock in my ass. He took his hands off my waist and grabbed my ankles as he continued to fuck. I was so turned on. I pushed back on his cock even harder and he returned the favor.

I was so horned up I blurted out that I wanted him to cum in my mouth. He continued to pound away not acknowledging me. I wasn't sure how it would finish but I didn't care.

He soon pulled out saying that he was cumming. I quickly got off the bed and onto my knees. He pulled off his condom and shoved his cock back into my mouth. He felt twice as hard the last time in was in my mouth.

He slammed his cock into the back of my throat as I submitted to his desires. He kept thrusting and thrusting until I felt it. His load shot to the back of my throat as he moaned. I eagerly sucked him up as he continued to shoot and fuck my mouth. I kept at it until he started to slow down and soften.

He was exhausted and I was in heaven. It was every thing I expected and so hot. Although I didn't cum my panties were soaked. I felt so feminine and so validated.

He got dressed and said his goodbyes. I showed him to the door and closed it behind him. The encounter raced through my head. It couldn't have gone better. I was already thinking about what is next. I decided to stay the night and finish off the wine. The first two encounters were near perfect. I couldn't wait until our third!!