I Would Never Kiss a Guy

I scooped up my pantyhose from the floor, along with my panties and teddy and put them all in the wastebasket. Done! I got in the shower and prepared myself for a day of manly stuff. My agenda was full; bank, groceries, oil change for the car, etc.

After my shower I dressed in boxers, jeans, t-shirt and sneakers, it felt good to put all that sissy stuff behind me, I planned to purge the rest of my girly wardrobe later in the day. Off I went to run my errands, the bank was first. I went inside and was helped by a teller named Lisa, who immediately caught my attention with her beautiful nails, as she sorted through my cash and checks for deposit. Her nails were a pale blue and she had several rings on her fingers, so feminine!

From the bank I went to the grocery store, which took forever. I noticed several girls wearing yoga pants, another weakness of mine. As I glanced at them in the store, I wondered if any of them would have any interest in me. I’ve never had much luck with hot girls since I’m only 5’6” tall and have a slim body type…besides being very shy around attractive girls. It was not hard to conclude that they were all way out of my league.

I arrived home about 2 p.m., put the groceries away and headed to my closet to get rid of all my pretty clothes. I opened the closet and headed to the very back where I kept my secret stash. I pulled out my red satin dress, my leather skirt, my PVC pants, so many tops and blouses that I’d forgotten I’d bought, then came the shoes and I had so many pairs. My sexy black heels with the ankle strap, my red Maryjanes, my shiny nude pumps, my comfortable flats, which I wore so many times cleaning my apartment. So much pretty stuff!

When I was done, I went into the bathroom and emptied the trash can of the things I’d put in there earlier. With it all in a massive pile, I stepped back and looked at it. It seemed like a waste to just throw all of this out, after all I’d purged so many times in the past and always rebuilt my collection. Was I sure about this?

I saw my cum-stained pantyhose on the top of the pile, “I really should wash these,” I thought to myself, “what if somebody finds them in the trash? I might as well wash my panties and teddy too.” I took my things to the laundry room and found the Woolite (Woolite is so good for delicates, btw!), filled the sink with warm water and gently washed them. These particular pantyhose were tan, very shiny and full support, they’ve always felt so good on my legs, so nice! I could feel myself wanting to keep them, “just in case.”

I finished washing my things and hung them on the drying rack, then went back to the closet with garbage bags in hand. I started picking up my pretty clothes and became so sad, I hated to get rid of these things. The more I sorted through them, the more reluctant I became to throw them out. I then realized I forgot all about the lingerie I have in my dresser, that stuff (bras, panties, pantyhose, girdles) would all have to go if I was going to turn a new leaf and be masculine.

I went to my dresser and opened the top drawer, immediately I saw a pair of my favorite pink hipster panties and my heart skipped! I was losing this battle, I couldn’t resist, I pulled off my sneakers, my jeans and my boxers and stepped into my panties! Oh what an amazing feeling! Pure bliss!

In just my panties and t-shirt, I ran back to my closet and started hanging up all my clothes again. I took out my phone and earbuds, loaded up my “girl power” playlist and started dancing around like a total sissy while I carefully put back all my pretty things. What was I thinking? I love women’s clothes and I love being a submissive girly gurl! What’s more I was not even sexually excited at this point, I just felt free and at peace with myself. At this point I realized I was purging the wrong clothes, it was my male stuff that had to go. I marched to my dresser and pulled out all my boy underwear and shoved it into a garbage bag, then pulled my jeans on and took the bag directly to the apartment dumpster! Gone!

After my closet was back in order, I knew I had some serious thinking to do. I had about 30 hours to have an answer for Nate. As promised, he hadn’t texted or called me and I was missing him. I really liked the things we did together, I’d never been that excited before and he made me feel special. Thinking about him got me excited, but I knew that if I allowed myself to cum my attitude would change and I would go back to being confused again, so no cumming!

I stayed home Saturday night and took a long bath, I shaved my legs and the rest of my body, which is something I’d been doing for a couple of years anyway. I then painted my fingers and toes a candy apple red color, so sexy! I pulled on a silky black nightgown and some tight panties, then proceeded to do my full-face makeup. I practiced my cat-eye skills with my eyeliner and went with a creamy red lip color to compliment my nails. This was all pure bliss for me!

After I was done with my makeup, I slipped into my silky robe and slippers and went off to the living room to watch a movie. I needed to distract myself, getting horny was not an option, cumming would not be a good thing.

I drifted off to sleep on the couch, woke up at 2 a.m. and went to bed. I kept my makeup, nightgown, and panties on. I slept like a baby that night. Sunday came early and I woke up in a state of horny frenzy. I wanted to relieve myself so badly, I refused to let it happen. I took an ice cold shower, put on some not-as-sexy panties, jeans, and a bra, then went about my day.

It was nearing 10 p.m., the time I needed to text Nate and I was a wreck. My stomach was making noises, my palms were sweaty, I as dizzy…a total mess, but I’d made up my mind, I would respond “yes”.

I picked up my phone at 9:59 and waited for the minute to pass. I typed “yes” into the text field and waited, one last chance to back out, then I hit send. And I waited for Nate to respond…typing….typing….typing…ding! “Good girl Gabby, you’ve made me so happy! I’ve missed you so much this weekend!” I typed “me too, but I’m really nervous. When can I see you again?” Nate shot back, “tomorrow night, come to my house and be prepared to spend the night. Oh, and I want the full Gabby, nothing masculine about you, got it?” My throat was like a desert as I typed “ok”.

I could feel my small cock raging in my panties, I couldn’t believe I was doing this! I didn’t dare play with myself now, I would certainly regret it.

I spent the night tossing and turning, not sure if I’d done the right thing. Monday was a workday, so I got up early, put on a pair of pretty blue panties and got my pantyhose from the drying rack in the laundry room. As I pulled them on I was so thankful I had not thrown them out, God they felt good!

I will spare you the details, dear reader, of a boring workday in my home office. Around 4 p.m., Nate pinged my phone, “be at my house at 6 sweety”. I loved that he called me sweety! I wrapped up my work and took a quick shower, making sure I was squeaky clean in all the right places. My nails were still in perfect condition, so I was happy to not have to fix them. I went to my makeup table and got myself ready for my Man (that sounded so strange the first few times I said it to myself).

I dressed in a brown, mid-calf leather, tight leather skirt, nude hose, nude 4” heels, and a white silk blouse with a huge sissy bow at the collar. I put on some cute rings, some bangles and my auburn, shoulder-length wig. I looked more girly than I’d ever looked in my life and I loved it!

I got to Nate’s house and he was in jeans and a dress shirt. He hadn’t shaved in a few days and had that rugged, manly look about him. He smelled so good!

Nate invited me in and gave me a hug and a kiss on the cheek. I reached up and put my arms around his neck and kissed him on his cheek. His stubble tickled my lips and make me laugh a little. Nate took my hand and led me to the kitchen where he had prepared an elegant Italian dinner and wonderful white wine. I felt like a princess!

As we ate, we talked about the future. I knew Nate wanted a very feminine partner, I didn’t know how far he wanted that to go though. I explained to Nate that I did not want to fully transition, I love my boy parts, but I would be open to hormone therapy and complete feminization short of surgery. Nate agreed, he did not want a female, he wanted a feminized beta male who would be willing to be his wife someday. Wife! Swoon! That word sent chills down my spine.

Nate went on to tell me that his sister Kara was a makeup artist and hairstylist. He told me she knows about the kind of partner he’s looking for and she would be helping me perfect my look. That part made me a little nervous, nobody besides Nate knew my secret at that time. Nate also said he wanted me to continue my career in software as long as it did not interfere with my duties in the home, which consisted of everything a housewife would do.

After dinner Nate led me to the bedroom, which was complete with pretty roses and candles. He turned on some soft music and began to kiss me. I immediately got hard as he explored my mouth with his tongue. I really needed to cum soon.

Nate eased me back on his bed and unbuttoned my blouse, then started rubbing my tummy with his manly hands. I was straining in my panties and pantyhose as he worked his hand down my skirt! I was dizzy with excitement and really about to lose control. I leaned up, unbuttoned Nate’s jeans, reached in and took hold of his cock in one swift movement. My hands were shaking as I kissed the tip of his raging hard-on. I had never touched another man before, but this was coming natural to me!

Nate stopped me and led me off of the bed. Facing me, he gently put his hands on my shoulders and eased me to my knees. He stepped out of his jeans and boxers, and his maleness danced before my eyes in its full glory! Damn it looked huge to me!

I kissed the tip of his cock and worked my way down to his balls with my lips and tongue. I would feel his pulse with my kisses as Nate moaned with approval. Just then Nate grabbed my head and forced himself into my mouth, I gagged as his member met the back of my throat. Having only practiced on dildos in the past, I found myself unable to control the thrusting Nate was giving my mouth, but I did my best to please him.

After several minutes of throat fucking, I felt Nate’s cock suddenly get larger. He put his hand around the back of my head and let out a guttural groan as he dumped his seed into my mouth! I choked and gagged as he unloaded; I wanted to spit so badly. Suddenly, Nate pinched my nose, forcing me to swallow all he had given me! I’ve never felt so emasculated in my life! Heaven!

When he was done he told me to clean him off with my mouth, which I eagerly did, since I was still so incredibly horny. “Good girl, Gabby”, Nate said, as he stroked my head. “Now let’s talk about your pleasure.” “Yes! Let’s talk about that!” I said. “Well, I don’t think it’s proper for a lady to cum on the first real date with her man, I think we should work on a regimen of chastity, which is why I bought you this pretty little pink cage, doesn’t this look cute?” I looked up at him, I was about to cry….