New Tranny Girlfriend

As much as I loved being a teacher, I was burned out and tired of the low salaries and policies of seniority. I was in my early thirties and had spent the past year helping my friend's business get off the ground. One Saturday I decided to go to the mall to get some new work shirts and was disappointed to see one of my old students squatting near the mall doors asking strangers for money. I saw him look at me and then look down hoping I hadn't seen him. It didn't work and I approached Kyle. He had always been small for his age. Maybe about 5'4 and about 130 at best. His hair was longer than I remembered and I saw his nails were painted and he was wearing mascara. I had always suspected that he was gay, but never pressed him on it while he was in my class. He had graduated from high school my last year as a teacher and I had always wondered what happened to him. After a few minutes of making awkward small talk I asked him if he wanted something to eat. He nodded. I took him to the food court and he told me how his parents kicked him out a few weeks ago after he came out to them. He had been sleeping in the park and only had the clothes on his back. I told him that I was heading to Macy's and could get him some outfits if he wanted some. He was quiet for a minute and then spoke in his soft feminine voice. "I'd like too, but I wouldn't feel right... and... I'm not sure if you'd be ok with the clothes I like."

I put my hand on his, leaned in and whispered that I've always suspected his true nature and that he should buy some make up too. He blushed. We finished our meal and then I told him he had $200 to spend however he wanted to.

I got my dress shirts fairly quickly and then told Kyle to find me when she was ready to check out. About an hour later she had a cart full of dresses, skirts, tight tops, panties, bras, and some make – up. I laughed thankful that it was Labor Day and Macy's was having killer sales.

Kyle and I stopped at Target to get some toiletries for her and I told her that she could stay at my place for the night. We got to my place and I showed Kyle where the shower was and pointed her to the guest room where we put her shopping bags. She showered and quickly went into the guess room. I hadn't realized how long her brown hair was, but it went past her shoulders and was curlier than I remembered. I was responding to some work emails when I heard the guest room door open and saw Kyle in a cute tank top, pleated skirt, and some cute flats. She had some lip gloss on and had braided her hair. She turned around and I could see a lace thong peaking above his skirt.

Kyle looked beautiful. I could tell that she felt sexy since her hard on was lifting her skirt slightly. I told her she looked incredible and she blushed. I then asked her if she could model some more and she smiled, quickly turned around and came out of the guestroom over the next ten minutes showing me all of the other outfits she purchased. She told me that she had one more special outfit she wanted to show me and I told her I couldn't wait to see it.

About five minutes later she emerged from the room wearing a tight see through nightie with a matching thong. I had often sat at my desk as a teacher wondering what her body looked like under all of her clothes and now I knew. She had a smooth flat chest. Nice bubble ass and what looked to be a four inch cock that was hard and sticking out of her panties. I motioned her to come closer and she slowly walked. I silently laughed at how she hadn't taken off her sandals and how cute her small feet looked with her pink nail polish. She was right up next to me and I sat her on my lap. Her heart was pounding. I lifted her chin up and kissed her. She had chosen watermelon flavored lip-gloss and her lips were softer than I had anticipated. He skin was smooth and soft and she was grinding her hips against my hard cock. I reached for her tiny cock and she shuddered a little and then started moaning softly as I stroked it. I lifted her up and told her to sit down on the chair. She did and I spread her legs. I took her cock and started licking the tip. I could already taste her pre-cum and she blushed. I started sucking more quickly and stroking her gently. Her cock started tensing up and she immediately came in my mouth. It was quite a lot of cum for such a little cock. I buried her cock in my mouth and made sure to catch each drop and then swallowed it. It was bitter and a little salty and I loved it.

I stood up and kissed Kyle and undid my pants. She instantly grabbed my hard cock and started inspecting it. I asked her if it was her first and she nodded. She slowly stuck her tongue out and flicked it on my tip. She had her hands around it and wrapped her lips around its head. I could feel her moving her tongue around it and then she took more and more of it until I could feel the back of her throat. She gagged and then pulled back. I grabbed the back of her had and shoved my cock in her throat. She put her hands on my ass and I started fucking her face. She was gasping for air but took it well. I took my hands off of her head and she started stroking while sucking me. It felt so good but I really wanted to taste her asshole and then fuck her. I lifted her up and led her to the bedroom where I bent her over the bed. I hiked up her nightie and pushed her thong aside and started to lick her virgin boy pussy. It was a little musty but really tight. I had to work hard to get my tongue in it and she was already hardening. It had been a while since I had licked a virgin ass and I couldn't get enough of it. I spent a long long time lubing it up with my tongue as she moaned in pleasure.

I couldn't tell what she said because her face was buried in my comforter, but I pulled my tongue out of her ass and told her to say it again. She meekly asked, "Can you please fuck me?"

"Are you sure?"

She nodded. I laid her on the bed and started sucking her and slid one finger in her. She was tight. Soon I had two fingers in her and was just licking her cock to keep her from cumming again.

"Please?"

I knew she was ready. I pulled my fingers out of her asshole and licked them. I pulled her panties off. I got the lube out of my drawer and lubed up my cock and then put her legs over my shoulders. The tip of my cock was pressed against her virgin boy pussy. She was clenching so I rubbed it around gently. I couldn't push it in. I leaned forward, kissed her gently and told her it was going to be ok. I put my cock back against her boy pussy and eased it in slowly. It probably took me 3 or 4 minutes to get it in entirely. It was tighter than any guy or girl I had ever fucked. I slowly pulled out and then thrust in again just a little faster. Faster and faster until I was ramming my cock in and out of her and her hard cock was flopping against her stomach.

She was moaning and started to stroke her cock. I moved her had away since I had other plans. I fucked her hard and pulled out so she could lick my cock and then stuffed it right back in her. I moved her legs to the side of me and was fucking her missionary and kissing her. She had her hands on my ass and I could feel her reaching for my asshole and her fingers pressing up against it. I was thrusting hard and could tell I was going to cum. So could she and I thrust a final hard time in her shooting my load inside her virgin ass making sure that it was deep inside of her boy pussy. I kissed her still inside of her and slowly pulled out.

We were lying next to each other and she was gently caressing my hairy chest. We fell asleep like that and I didn't wake up until I felt her stroking her tiny cock. I asked if she was horny and she nodded. I got up, handed her the lube, and bent over. She hesitated so I leaned forward and spit on her cock and started sucking it. She was really hard. I took her cock out of my mouth put some lube on it and bent over. Being so small, she slid into me pretty easily and started fucking my slowly. I turned around and told her faster. She was good at following orders and lasted about another 30 seconds before she came. It felt good to feel her cum in my ass. She pulled out and I stood up and hugged her kissing her on her forehead.

We got cleaned up and she put on her new sundress for our first official date. That was just over a year ago and she's still my girlfriend. I'll be posting some more stories soon about our kinky adventures.