Frankie and Johnny

urtles53 - 03/09/2026

Johnny had just turned eighteen in the Spring of 1966, the year he graduated from high school. Life had been a little hard for Johnny through the years. He just felt so different from everybody else. Johnny really had no close friends and for sure would not be attending the senior prom or any of the other graduation festivities. He would no doubt go home right after the graduation ceremony. Johnny knew he had to go just for the sake of his parents and older sister attending, but he had no invitations to any after-graduation parties. The problem was Johnny felt more like a girl than a boy and always had. This was long before LGBT rights came into being, plus, he was brought up in a very religious and conservative household. Johnny's dad knew something was off with him and gave up on him as a kid. He had hoped Johnny would become a high school football star like he was. Little did he know that Johnny had fantasized about being his high school's prom queen instead and making out with Rod Jansen, his high school's stud quarterback, in the back seat at the local drive-in theater. Johnny was also very slim, pale, petite, and girlish-looking. He had no body hair and also had a small penis that made him embarrassed taking showers in gym class. Everyone else always looked so big! He had even been teased a few times about his 'teenie weenie' by the other boys. That made even thinking about having a girlfriend tough, especially since he felt like a girl deep inside. What Johnny really wanted was a boyfriend, but he didn't have a clue about how that worked. Johnny would fantasize about kissing other boys in school while dressed as a girl. Johnny also fantasized about having a boy stick his penis up his butt. He would always steal one of his mom's cucumbers to feed those fantasies. It always felt so good, like it was meant to be. Johnny's butthole was actually getting stretched out pretty good. Another proclivity Johnny had was dressing up in his older sister's clothes. When no one else was home, he would go the whole nine yards, with panties, bras, skirts, blouses, dresses, etc. Johnny would even put on his mom's wigs and make-up. He was getting good at it and ended up a pretty girl after such a session, as Johnny's facial features were very feminine to begin with, so it wasn't much of a stretch. It made him feel so very special and real. Johnny wanted so much to be a woman. A new neighbor has just moved in next door to Johnny's folks' place. His name was Frankie, looked to be in his forties, was single, and was some kind of salesman, according to Johnny's mom. She said he was very friendly and it looked like they lucked out on a good new neighbor. Johnny had waved to him a few times as he came and went from school, but they hadn't spoken yet. He did think Frankie was very handsome and distinguished-looking. Then one afternoon Johnny saw Frankie working out in his yard in shorts with no shirt on. Frankie was tan and muscular and looked like Tarzan! Johnny could not get that image out of his head and found himself highly sexually attracted to Frankie. Johnny jerked off several times that night fantasizing about making love with Frankie. Johnny had had a few crushes in his life, but this one was almost surreal, and he didn't know what to do about it. The next afternoon Johnny's mom called to him in his room. "Johnny, come on down and meet Frankie, our new neighbor! He has a favor he wants to ask of you." Johnny was instantly nervous and excited at the same time! He went downstairs, and Frankie was sitting with his mom in the kitchen over a cup of coffee. Frankie looked even more handsome and masculine up close. Johnny was shy, but Frankie was super personable and put him at ease quickly. "Hey, Johnny, nice to meet you face to face after waving for a couple of weeks!" Frankie chuckled, "We're 'Frankie & Johnny', just like the song, only I'm not a girl!" Johnny thought, yes, there was no doubt Frankie was all man! Johnny would be quite happy to be the girl in this case! Johnny also picked up on Frankie looking him over pretty good. Johnny just had on short shorts and a tank top covering his slim, pale body. Could it be possible that Frankie was telegraphing sexual interest in him? "Hey, Johnny, I am going on a business trip for a week and wondering if you would check in on my two cats daily, Abbot and Costello. I pay well!" Frankie quipped, "If you're free, come on over to my place around six tomorrow, and I will introduce you to them." "You bet!" Johnny replied, "I love cats!" "I thought you might!" Frankie quipped, "I'm pretty good at reading people!" Johnny arrived right at six the next day at Frankie's door. Johnny was again dressed in short shorts and a tank top, as that seemed to be the outfit Frankie liked to check out. At least that was the fantasy Johnny had in his head. Frankie greeted him at the door in almost the same outfit, shorts and a tank top! At least they were on the same page in fashion! "Hey, Johnny, right on time!" Frankie laughed, "I like that! Now feel free to hang out at my place after you feed and look after the cats too. Watch TV, take a dip in the pool, lay out in my yard, whatever you want. The cats will enjoy the company. I will be gone a week, until next Friday" Frankie introduced Johnny to the cats, showed him around the house, and gave him a house key. The house was decorated beautifully and with sophistication. Johnny still got this feeling that Frankie was checking him out like a guy would a girl. He put his hand on Johnny's arm several times while showing him the house. It gave Johnny goosebumps. Frankie left the next morning, and Johnny went over in the late afternoon to check on and feed the cats. He hung out a while and petted them on the couch and noticed some photo albums on the coffee table. Johnny just casually opened one of the albums up, and his eyes practically popped out of his head. They were all pictures of Frankie kissing and having sex with women. That is, until Johnny looked closer and realized these 'women' had penises! They were all guys dressed up like girls! Johnny was stunned. Had Frankie left these out for him to discover? That seemed like it had to be pretty obvious. These photo albums certainly were not hidden away. Johnny got an instant erection and masturbated right in front of the cats! One thing Johnny did know was that he was hotter than any of those lady boys in the photo album! Had his ship finally come in? Johnny had the whole week to study the photo albums. He had never seen anything like this before and did not even know it really existed in the world. It was very freeing and exciting! He finally saw how sex between two men worked, even if one was dressed up as a girl! Johnny could see himself doing everything in the photos and enjoying it very much! He took mental notes. Frankie looked very tender with his lovers too, with lots of kissing and fondling. Johnny liked that idea a lot! And all of Frankie's 'girlfriends' were in such sexy outfits too, way better than his sister's wardrobe. Baby doll nighties and lingerie, lace panties, stockings with garter belts, wigs, make-up, the works. Johnny would love to wear those kinds of things! He was ready. He couldn't wait for Frankie to come back home. He just knew he had left these albums out on purpose. Johnny wanted to be Frankie's newest and best 'girlfriend'! As soon as Frankie returned home, he called up Johnny on the phone to thank him and invite him over for a BBQ that evening. Johnny was maybe feeling his instincts were correct about Frankie and hoped this would be the night he lost his virginity. Johnny was nervous, but excited. He took the best shower of his life, making really sure to wash his butthole extra good. He then put on his shortest shorts and a pink tank top. If Frankie did indeed want to bed Johnny down, he was hoping Frankie had some sexy lingerie he could wear. It was showtime! Johnny knocked on Frankie's door and was met literally with open arms, a good start. Frankie told him how grateful he was for the good care his cats received, and it made him feel better on his trip knowing they were being looked after. They went out back by the pool where Frankie had burgers on the grill. Johnny had already decided to ask Frankie about the albums he had left on the coffee table once they ate and got the small talk out of the way. Johnny figured there was no way Frankie didn't leave them there on purpose for him to discover. The moment of truth had come. "I couldn't help but notice the photo albums you had on the coffee table." Johnny blurted out nervously, "I had never seen anything like that before." " I left them out special for you based on a hunch I had." Frankie said softly, "Did you like those photos?" "Yes, I did." Johnny said after a brief hesitation, "I guess your hunch was correct." With that, Johnny broke down and told Frankie everything: his wanting to be a girl, dressing up in his sister's clothes, wanting a boyfriend, even about sticking a cucumber up his butt. Frankie listened to it all with a gentle smile on his face. Then he bent over, hugged Johnny, and gave him a sweet kiss on his lips. Johnny melted into Frankie's arms with a moan escaping his mouth. The sense of release was palatable. "Johnny, I knew all this about you from the very first time we met." Frankie softly whispered into Johnny's ear, "I could sense you needed some loving and understanding. I even bought you a few gifts on my trip. Come with me and let's check them out. I am betting you are going to love them." Frankie led Johnny by his hand to his bedroom. Laid out on the bed was beautiful lingerie, a lacy garter belt and stockings, a long-haired wig, and a bag full of make-up. Johnny was almost shaking with excitement. Frankie was making his dream come true. "Johnny, take all this into my bathroom and put it all on. I know you will do a great job. I can feel it," Frankie said softly. "Then we are going to make beautiful love together on this bed. Tonight you are going to be my girlfriend." Johnny gathered up all his gifts and scampered into the bathroom like a sissy. His female side had already kicked in full force. He quickly took off his clothes and slowly and sensually put on the lacy panties and stockings and baby doll nightie. They were beautiful! The wig fit perfectly and matched his own hair color. Johnny applied the make-up flawlessly, as Frankie had predicted he would. Johnny admired 'herself' in the mirror and had to admit what 'she' saw was very sexy! Suddenly Johnny's nerves settled down. Now 'she' could be who 'she' really was! Johnny even decided to use a new name in this persona. Tonight 'she' would be 'Joanna' and give Frankie the best sex of his life! Joanna had memorized all the photos in those albums! Joanna floated out of the bathroom and saw that Frankie was already in bed, apparently naked under the covers. Frankie's eyes widened, and a smile instantly graced his lips as he beheld the sexy splendor that just appeared before him. Joanna was beautiful and desirable beyond belief. Johnny had transformed into a woman. "Johnny, you are even ten times as sexy and beautiful as ever I imagined you would be!" Frankie proclaimed, "What sweet love we will make." "Tonight I am Joanna." Joanna announced, "I have been Johnny for way too long." As Joanna approached the bed, Frankie pulled back the covers to indeed reveal he was naked and sporting a very impressive erection! Joanna was instantly trying to compare it to her cucumber dildos and decided she could handle it! Joanna straddled the naked Frankie on the bed and bent down in the first kiss of many they would share. She melted on top of him in pure sensuality as the sound of kissing and moaning filled the room. Joanna had just entered heaven for the first time in her life. Frankie then flipped Joanna over on her back, as the deep sensual kissing continued. Then he got up on his knees between Joanna's legs and beheld the sexy and beautiful view below him. Joanna's little 'clit' was stiff and quivering beneath the lacy panties where a wet spot had formed. "As pretty as these panties are, I think they would be prettier on the floor." Frankie said with a smile, "There is something much prettier under them that I want to kiss and suck on." With that, Joanna raised her hips as Frankie slid off her panties and her stiff 'clit' slapped back against her belly. Frankie bent over and kissed Joanna sensuously on the lips and then worked his way down her body, kissing all the way until he reached her 'special place'. He slowly engulfed her swollen 'clit' into his mouth and gently sucked on it. Joanna thrust her hips against Frankie's mouth as she moaned and sighed. She wanted this to never end. Frankie kept her on the edge of having an orgasm, something he was an expert at with all his lovers. No, he had plans for some serious sex with this little vixen tonight and didn't want her blowing her load too early. Frankie then reached over to his bedside table drawer and brought out the Vaseline jelly and rubbed some on his cock. He spread Joanna's legs apart and pushed her back a bit by her thighs. He positioned his cock right at the entrance of Joanna's asshole. "Joanna, I want you now. Tell me instantly if it starts to hurt. I will be as gentle as I can until I see where we are at. I believe you working out with the cucumbers will make it work, but I want you to feel good too. You are just so damn sexy I can't wait any longer!" Frankie slowly stuck his cock in Joanna's 'pussy' and slid it right in with no problem. Joanna let out a slight gasp, but a look of ecstasy swept over her face. Frankie had never felt such a perfect fit in his many lovers and slowly began thrusting. Joanna raised her hips and met every thrust from Frankie. The pace, rhythm, and passion of the thrusts increased as they started to share deep kisses and looked deeply into each other's eyes. This was not just raw sex; this was making love. Johnny had finally become the woman he had always dreamed about. Frankie continued to fuck Joanna with increasing intensity. The sounds of her moaning and the slapping of thighs filled the room. Finally, with a loud groan, Frankie emptied his balls into Joanna's butt. That set her off as she came all over her own belly, and she squealed passionately. He squeezed every drop he could into Joanna's 'cunt'. They slowly and tenderly kissed as they gazed deeply into each other's eyes. That had been a magical moment for both of them. Frankie and Joanna were still full of passion after a bit, and he patiently put her through the paces and taught and showed her all the different positions they could enjoy. Frankie pumped Joanna's butt with another load of baby batter doggie style, and they ended up the night with him shooting his last load in her mouth and all over her face for her first blowjob. Joanna was a very apt student and her butt held up well. They cuddled and kissed for a while before Joanna got up and changed back to Johnny. The reality was he would never completely change back to Johnny from here on out. Frankie had awakened the woman in him. Joanna indeed became Frankie's favorite girlfriend, and they made love almost every day that Summer until Johnny went away for college and a whole new world of sexual adventures!