Blind Date at the Drive-In
As the two siblings got older, Karen's idea of having fun with a crossdressing brother changed. Ever since she began dating, she thought it would be amusing to see how her "little sister" handled boys too. She knew he could be dressed up and made up realistically enough to fool a boy up close, and wondered if Kim would actually like it. An unformed thought came to her: if he did like it, perhaps that mean he wants to become a girl, or that he should become a girl but doesn’t know it yet. Dressing him up and setting him up one-on-one with a guy would be an interesting way to test her theory.
So, one Saturday when Kim was fifteen and Karen was in college, Karen got him to go on a double date with her current boyfriend, Chuck, who was a senior at their school, and his best friend and teammate on the football team, Rick.
She styled Kim’s longish hair, and dressed him in pink control panties and a matching A-cup bra, which she filled with little silicone inserts she called "boy cheaters." Then she had him put on a tight white midriff top, plaid miniskirt, anklets, and flats. Kim's pulse raced as he looked in the mirror. The short skirt and bare midriff made him feel very sexy. The cheaters even had subtle nipples that pushed through the top, giving him a realistic feminine look.
“Oh gosh, Karen, I love the outfit,” he gushed.
“Well, the true test of a girl's outfit was whether her date likes it,” Karen replied. “Don’t worry, though. Rick will love it when he sees the young, fresh, female Kimberly.”
As they waited for their dates, Kim's mother told them to have fun and be careful. Karen convinced her that it was just for laughs, and was going to be a very casual movie date. She promised to watch Kim like a hawk, and make sure "nothing happened." The nervous boy assumed she meant that there would be no kissing – and that was fine with him!
Looking over her pretty little boy, Kim's mother smiled lovingly and said, "Kim, you would have made a lovely girl. I never realized just how beautiful my younger daughter Kimberly truly is!" Kim's heart skipped a beat at her sweet words. That's just how he felt, beautiful.
He hoped his date would think he was beautiful, too, and he could completely fool the boy into believing he was a real girl. Kim imagined that the boy would want to hold hands in the theater, and maybe try to put his arm around the pretty boy. Kim wasn’t sure he would allow that, but really looked forward to their goodbye. He hoped he would excite the boy enough so he would want to kiss him. Kim didn’t actually want to be kissed; he just wanted the boy to want to kiss him. Kim figured he would let the boy kiss him on the cheek, or maybe he’d be brave enough to give the boy a quick peck on the lips if he was nice. Then once he was safe inside afterward, he expected to get a good laugh at the boy’s expense, thinking how the guy would be falling in love with his feminine image, never knowing Kimberly was really a boy!
Right on time, the doorbell rung when the boys arrived. Rick was several inches taller than Kim, had a broad chest and strong arms, and seemed very polite. Karen introduced him as Kimberly, and he was excited at the attention and flattery the young man paid him. Especially since Rick was the type of macho guy who tormented him at school. Kim marveled how a boy's attitude was so much different toward him when the boy thought a he was a she. This wasn't so bad, being a girl, he thought. Kim felt butterflies inside as the young man firmly took his slender hand and led him to the back seat of the car where he would soon learn that being a girl is more than being worshipped from afar.
During the ride to the movie, Karen and the guys mostly talked about the big game last week, and it seemed that Chuck had thrown the pass and Rick made the catch to score the winning touchdown. Kim really didn’t care, but played along with Karen’s subtle encouragement on how to act like a girl and made sure he showed the proper amount of enthusiasm. He was afraid he went a little overboard in his gushing praise, calling Rick his “football hero,” but Karen seemed delighted. He assumed she was pleased with his performance.
It was when the car turned into a drive-in theater that Kim got the first indication their sweet double date was more dangerous than he had imagined it would be. As soon as they parked, Karen slid over to get cozy with Chuck. She leaned her head on his shoulder, blocking Kim’s view, so Kim had to move next to Rick to see the screen. Instantly the man’s arm was over and around Kim’s shoulders, cradling the boy’s elbow in his large hand and pulling him close to his muscular chest.
Kim had imagined that Rick would be like the boys his own age who would slowly and clumsily try to sneak his arm around the girl in a crowded theater. Now he immediately found himself in the arms of creature very unfamiliar to him, an adult male, in the semi-privacy of the back seat of a large sedan. The heat of Rick’s body, his musky aftershave, his possessive attitude toward his feminine companion put the boy on edge.
Things were pretty cool that way for a while, but began to heat up when Karen and Chuck started making out in the front seat. Kim was shocked at how blatant they were. He knew Rick had to be getting ideas of his own about his date. And it wasn’t long until the man reached his free hand across Kim’s face and caressed the boy’s smooth cheek. He turned Kim’s head toward him – Kim didn’t realize why but cooperated and looked in Rick’s eyes – and then it happened.
His first kiss. He was shocked and tried to not tremble. Rick’s hard lips and trace of stubble were so strange. He couldn’t help but feel anguish that he should be kissing a girl, instead of being the girl. He was also afraid that Rick would somehow be able to tell from kissing that he wasn’t a girl. He had to act like it was normal for him to kiss a boy, and that he wanted it and liked it. The problem was he didn’t know how to kiss. He had been prepared for a quick goodnight kiss at the end of the evening, but suddenly had to deal with Rick as he hungrily worked his way across the sissy’s painted lips. Kim tried to keep calm and relax his lips a bit, pretending he wasn’t terrified by Rick’s aggressive intensity.
Kim saw a movement in the corner of his eye and in the nick of time stopped Rick’s hand from grabbing his padded chest. Without missing a beat, Rick put his hand on Kim’s thigh. His powerful hand began caressing the soft naked flesh, pushing his skirt back inch by inch. Kim understood how vulnerable a girl in a skirt must feel, but felt it had to be even worse being a boy in a skirt. He pressed his knees together and pushed Rick’s hand away again, and again, but Rick persisted.
Karen and Chuck had slid down so Karen couldn’t see them. Their noises from the front seat made it clear they were past the kissing stage. Chuck had to be sucking her nipples, and judging by her moans, Karen loved it. Kim knew that Rick had to be getting frustrated with him, with his friend being so successful. Finally, after pushing Rick’s hand away for about the twelfth time, Rick blurted out, “C’mon, Kimberly! What’s the problem?”
Picking up on the tension in the back seat, Karen’s head popped up. Kim was right; Karen’s blouse was open and she was fastening her front-close bra. She quickly arranged her breasts and buttoned her blouse.
“Hey, Kimberly, I think we need to go to the ladies’ room, little sister. Hmmm?” Her tone made it clear it was not a request. “Chuck, Rick, we’ll be back in just a bit.”
Desperate to get away from Rick and glad to be rescued, Kim happily agreed. Karen pulled him along by the hand in a stony silence. He was planning to tell Karen how upset he was to be forced into this embarrassing and potentially dangerous situation, but when they got to the restroom Karen laid into her little “sister.”
“Kimberly, you are totally embarrassing me! You’re acting like some stuck-up little prude! You know, little sis, Rick has certain expectations. He’s a college senior, after all. There’s going to be trouble if you’re not nice to him. He knows you’re still in high school but you don’t want him to find out you’re just a sophomore, do you?”
She was talking to Kim like he was really a girl!
“But I am a sophomore, Karen – hey, wait a minute.” He realized something else was going on here. “What does that have to do with it? What did you tell him about me?!”
Karen leaned in with one leg out, hand on her hip. “Kimberly, sweetie, do you really think he’d go out with a fifteen-year-old? I told him there’s two years between us, not four, which makes you s*******n and a senior. And to make certain he’d take you out, I mentioned that you don’t know much about football, but you do like football players – a lot. I said you like jocks.”
Kim was stunned. Rick not only thought Kimberly was a real girl, but an experienced, horny high school senior who goes for jocks – they type of boys who despise him! And by following Karen’s prompting on the drive, Kim had played the role without knowing it, increasing Rick’s “expectations.”
Clutching his purse in front of him in shaking hands, Kim whispered, “Oh, Karen, I'm scared. I just thought we would cuddle. What should I do?"
Karen looked into her sissy brother's pretty face. He looked like a frightened doe, with big eyes and long lashes coated with mascara. She though what a poor excuse for a boy he was, nothing like the chiseled young men that waited for them back in the car. They would never think of putting on a bra and falsies, panties and a skirt, and get in the back seat of a car to cuddle with a horny guy, to see what it's like to be a girl.
She knew the date was her idea, but the fact that Kim was willing and eager to go along with it made her think that maybe he deserved anything that happened to him tonight. But she couldn’t let him get hurt, and knew there was only one way for him to keep his secret. It also dawned that this casual date was turning into a greater test than expected of her theory about Kim’s sexuality, and a way to see just how far he’ll go as Kimberly.
Karen knew Kim had no experience with girls, so she decided that his first experience with sex would be as a girl – with a boy – and it would be tonight.
In a soothing tone she explained her plan. "Kimberly, you need to understand that he's not trying to please you, just get you hot enough to please him. If you don't want him to touch you, you have to take the initiative and touch him. Make him happy, and he'll leave you alone afterwards." Somewhat sarcastically she added, "Then you two can cuddle."
"Touch him? Make him happy? What do you mean?" Kim looked confused.
"Back in the car, when he reaches for you, just take his hands away and reach for his pants. Start rubbing him there, you know, stroking it. He'll probably come in his pants and you'll be done."
Kim’s eyes popped out in horror. "Oh my god! Make a boy come? No. NO! I couldn't do that! I'd rather die first!"
"You won't die, probably,” Karen smirked, “but if he discovers your itty-bitty secret, he's going to get really, really mad. I’m sure he won’t get physical, but you can’t stop him from spreading the news about you all over town. I'm sure the boys in your school will be very understanding about your little hobby. Think how popular you’ll be! I bet they'll all want a special date with little Kimberly!"
Thinking about the cruel boys in school made Kim go white. He'd be branded for life if this got out. They would beat him up, or even worse they might force him to do things he didn't want to think about it. He might as well die, for the humiliation he would face. He reasoned that maybe Karen was right.
"So just, sort of stroke him, in his pants?" Kim asked meekly.
"I'm sure you know how to do that, little sister," Karen laughed. "You know what feels good for a boy. Here," she said, handing Kim some tissues. "In case any gets on you, you can wipe up."
Kim felt nauseous. "Can't we just leave? Please?!"
"No! Now do what I say, or he won't stop trying to undress you," Karen retorted. She looked into her brother's deep blue eyes and softened her tone. "Kimberly, I'm sorry. But trust me, everything will be fine if you take control. Every girl has to do it for a boy sometime, and tonight it's your turn. Just remember, he's excited because he thinks you're a girl, so be a girl. You're a girl and he's your boyfriend. And you’re a lucky girl! All the other girls are so jealous of you dating a college man. Right? Adopt that mentality and you'll do just great. C'mon, let's go back. You boyfriend is waiting for you."
Kim’s heart began racing when he opened the car door and saw Rick’s arm stretched across the back of the seat waiting to engulf him. Forcing a sweet smile, the pretty boy slid across the back seat until their hips and legs touched, when he was quickly enfolded in both of the man’s strong arms. Kim felt himself being turned toward Rick, who leaned in and nuzzled the boy’s neck with his raspy cheek.
“Feeling better now?” he whispered, obviously expecting that Kimberly’s sister had straightened her out.
“Uh huh,” the youth murmured. Kim’s hands came to rest on the man’s biceps. He squeezed the muscles, and felt the force he had to control, the anger he had to avoid.
“You like muscles, I hear,” Rick said.
Kim tipped his head up to respond to Rick’s question. “Uh huh,” he began to say, but his voice was smothered by Rick’s impatient kiss. Then Rick’s free arm moved, and Kim felt pressure on his chest. Rick’s palm had pushed against his padding; if he squeezed, he would instantly know the truth. Kim had to take control – now!
He forced a smile and moved the hand away. "I'm sorry, Rick. I get a little tender there, y'know, at that time of the month," he whispered with a pleading smile. Rick’s chest deflated. Then Kim did something he never imagined he would do. He tenderly kissed Rick right on the lips. Then, as Karen had instructed him, he reached across with his left hand and laid it on the older boy's crotch. He felt the bulky, coiled manhood start to awaken at his touch. His eyes grew wide.
"Hey, now that's better, honey," Rick hoarsely whispered. “I see you like what you found.”
He pulled back a little, letting Kim’s head rest on the man’s upper chest, tipped down. Now Kim was forced to watch himself slowly rubbing the man’s groin, rather awkwardly, with his palm, trying to not actually handle it with his fingers. He almost felt like crying as it stretched out to point straight at him. Rick moaned with pleasure. Although Kim was disgusted at the chore he was performing, he figured he had better make Rick feel good to get this over with as quickly as possible.
Kim wondered what a girl would do at a time like this, and figured a girl would respond to her boyfriend's enjoyment by getting into the act. A girl would think this was great and do something like – he reached his hand down between the man's legs to feel the shape of his weighty testicles, caressing them with his fingertips. He moved up to check the result – oh, my! – then caressed the lengthening tool with his fingers, tracing the outline of the older boy's excitement with his fingernails. Forgetting himself, Kim became hypnotized by its growing size and firmness. He gave it a squeeze at the root, then a few more, moving up toward the head. He wondered how it could still fit inside his date's increasingly tight pants.
"Hey, you're really into this," Rick whispered, giving Kim a quick peck on the cheek. “I know what you want.” Then, as if it was a prearranged signal, he called to his friend in the front seat, "Say, Chuck, I think it's your turn to, uh, go for some soda and popcorn." He sounded insincere, as if this was a signal between them.
"Sure thing, buddy,” Chuck quickly answered. “C'mon, Karen. I want to check out their arcade, too."
Karen was nervous about leaving Kim alone with an aggressive guy like Rick, but decided that their absence might spare him some embarrassment while he brings his date to orgasm. "Cool!" she relied. "Let's go!"
"B-but..." Kim stuttered and he started to sit up to stop Karen, but couldn’t move. Rick's arm had a vice-tight grip around the little transvestite’s shoulders, while his other hand had quickly moved to hold Kim’s forearm steady, keeping his pretty date’s hand gripping the bulge in his pants. Kim's heart leaped into his throat. This wasn't the plan! He was trapped!
As she slid over to the driver’s door, Karen was dying of curiosity to see what was happening in the back seat. "I guess we'll be a while. Have fun, you two!" she chimed, turning around. She had expected to see Kim facing forward and awkwardly reaching sideways across Rick’s lap, and was shocked to see how affectionate toward Rick he looked, nestling in the man’s arms. Also, he didn’t seem at all upset to be left alone with Rick, because he didn’t sit up or make any move to stop her. He didn’t seem embarrassed to be playing with Rick’s package either, because he didn’t move his hand the slightest when she turned around.
Kim was really getting into this, she thought, not knowing her brother was being held motionless. Maybe this proves he’s really gay, she mused, and his true nature is just coming out. Maybe I’m doing him a favor by getting him into boys. But a doubt still lingered in her mind – it was too dark to be sure, but was that a look of fear in his pretty eyes?
Chuck was calling her to come along, so she absolved herself of all guilt for whatever may happen to her brother, blaming him for being such a sissy. Then the car door slammed, leaving Kim alone to deal with a man with an erection.
"Alright! Now we have some privacy. Let's try this," Rick said, loosening his belt. Kim was terrified just by being alone with his date, and the guy was already undressing! The boy’s heart was racing and his head started to pound in panic.
"Unzip me," Rick ordered. The pantied boy didn't know what to do except play along. Caught up in the demands of his assumed role, he submissively obeyed. He managed to unbutton the waistband, slowly pulled the zipper down, and opened Rick's pants. Kim watched in awe as the young man pulled his cock out through the fly in his boxer shorts, revealing his arousal in the dim light. Kim couldn’t take his eyes off his date’s manhood. He became dizzy with fear and thought he might pass out.
Seeing Rick’s hard-on was a revelation to Kim. So, this is what men are like, what the boys at school are like when they get hard, he thought. He felt jealous; he was puny compared to them, but more importantly the sight crystallized his fear of them. If they found out about tonight, his life would be hell. Earlier he had imagined this date would be on his terms, but now it was on their terms – all the boys that had teased him. Pleasuring Rick would be like paying homage to all the locker room studs. But Kim knew he had no choice now; to complete his chore he had to actually touch it.
"Go ahead, Kimberly, I know you want it," the young man said. Almost in a trance, Kim reached over to take the naked flesh with both hands. His hands encircled the shaft, and he was surprised at how big a man’s cock actually got when aroused, as every girl discovers at her first encounter with one. The sissy boy slowly began squeezing, fondling, stroking it with his soft hands. He had done this to himself a few times, and now felt disgusted and humiliated to be doing another boy’s dirty work.
Yet as the older male grunted with pleasure, Kim began to understand the power a girl has over a boy. He figured Rick would like it if he quickened the pace a little. He felt a bead of moisture on its tip, and rolled it around the head with his thumb. He smiled at the man’s moan.
"That's nice, Kimberly, you sure know what you’re doing. Now, go down," Rick whispered.
"Go down? What...?" Kim wondered what he was doing wrong.
Rick chuckled. "Go down. You know, use your mouth, darlin'."
Kim was shocked at the suggestion. "I don't know... I never tried that before. I…I don't think so," he said timidly. He hoped Rick would understand and back off. Yet he knew it was something girls did for their boyfriends. His “boyfriend” thought he "wanted it." Would he act out of character if he didn't "go down"? Would Rick get suspicious?
"You never? I thought that’s what you wanted,” Rick insisted, his eyes locked on Kim’s eyes. “I can’t believe you’re a senior and you haven’t done that yet. C’mon, Kimberly, you’ll be so awesome. You’re such a loving person. And I really like you too, Kimberly. You're really special. You'll like it, too. All girls like it, especially when they swallow. That’s best for me, and it won't mess your clothes up that way, either. Chuck says your sister does it for him – don't you want to be like big sister? Come on, I can tell you'll be great! You obviously love cock."
Kim was following along but was mortified at Rick’s last words. Just because as a boy he knew what felt good, he had inadvertently made Rick think he “loved cock” so much that he wanted to “go down” on one – but never in his life had the boy even imagined such a thing. Yet now it was a reality. The notion was worse than the most terrifying nightmare Kim had ever had. But Rick had established his expectations and Kim would have to submit.
Kim felt sick to his stomach, but strange thoughts came into his head, alien thoughts for a boy. If girls like it, how bad could it be? Would I really be good at it, like he said? What does it taste like? But Kim's boy-self fought back against this bizarre temptation.
"No, not tonight. I'm sorry, maybe next time," he pleaded.
“Oh, c’mon, Kimberly,” Rick was getting upset. “You can’t leave me this way. You were so hot for it a minute ago, I thought that’s what you wanted all along!” He was definitely angry now. “Kimberly, you were the one that started stroking me! Don’t be a tease!”
Kim felt pressured to do it to keep his secret, but also had to admit that Rick was right. This was his own fault for trying to fool the young man, and he was just getting what he deserved. Rick didn’t deserve to be teased and then denied his pleasure; he couldn’t help his feelings, his desires. His very masculinity demanded from Kim a feminine response. If it was something a girl would do in this situation, he had to do it too.
The pounding in Kimberly’s head became worse, and a spasm of nausea twisted his stomach. He felt like a trap door had opened under him and he was falling, hopeless. He realized that he really had no choice and that in a matter of moments….
The thought of having a cock in his mouth was so frightening that Kim's mind would not accept that he would be used in this way. Recoiling from the shame, he wished that just for tonight he wasn’t himself – and then something clicked in his mind.
This whole scenario was too horrible, too shameful to be happening to Kim, so it wasn't. It was happening to Kimberly. Which meant it wasn’t humiliating. Rick would never get turned on by a boy, only by a girl. This macho football player would never pull it out for a boy, only for a girl. Kim knew that he would never want to do this, but a girl would – so I’m a girl, Kimberly thought. I’m Rick’s girlfriend.
In the back of his mind, he knew he was pretending, but once this switch flipped in his mind, Kimberly experienced new emotions welling up within him. He was overwhelmed by a sense of obligation to Rick, and that he shouldn’t be a tease. Then he felt like he was melting inside, that his body and mind were surrendering to the older boy's sexual power. He became weak in the presence of true virility, yet at the same time was flattered and excited. It seemed a privilege to be responsible for Rick's arousal, to experience this intimacy as a girl. It was like he was a secret agent, learning what only girls learn about boys, back seats, and hard-ons. A wave of tenderness and caring toward his date came over Kimberly. He wanted to be every bit the girl he had to be to make his boyfriend happy.
As his thoughts focused, Kimberly noticed that he had never let go of Rick’s penis and never stopped caressing it. And now it was time to go down on his date.
“Don’t tell my sister, okay?” he pleaded, looking up at Rick. “I don’t want my mom to find out.”
“Oh, I won’t tell a soul, Kimmy,” Rick lied, grinning, knowing he had made another conquest.
Rick guided him down off the seat. The skirted boy’s bare knees hit the carpet and his dream of being Kimberly really began. Like in a dream, he was perfectly calm in spite of his terror. He found it interesting that the man was basically fully clothed – easier to cover himself up if we get caught, Kimberly thought. It was strangely exciting to think that, on the other hand, anyone would know why he was on the floor of the car, kneeling between Rick’s legs.
The older male’s hard-on was inches from his face. Rick’s manhood seemed so enormous up close, standing upright like a proud soldier. It loomed even larger as Kimberly leaned forward, then it disappeared as he tipped it down and opened his mouth wide. Kimberly’s eyes focused on the boyish blue plaid of Rick’s boxers as he lowered his head, as the underside first brushed against his tongue, as his lips closed around the warm cockhead.
To take the very core of Rick’s masculinity inside his own body stunned the boy. He felt utterly defeated, yet warm feelings toward his conqueror rushed up within him. He felt Rick playing with his hair, tucking some stray locks behind his ears. He glanced up at the man; their eyes met. “Good girl,” Rick murmured. Realizing he wouldn’t be groped while he was doing this, accepting that Rick saw only a girl, Kimberly began to feel confident, in control. I’m a girl, I’m a girl, I’m a pretty girl, floated through his mind.
This idea freed Kimberly to fulfill his role more completely – to add a new dimension to the dream. Subconsciously, acting like a girl who felt affection or even passion toward her man was the best way to deny the shame he really felt. It also sparked a fantasy in the sissy’s mind. This wasn’t ****, it was romance. Kimmy did this for Rick every week. They had been dating for months, this is how she held on to her college man, her football hero, and all the other girls at school were jealous because Rick was such a jock and so well-endowed. Moving his mouth around the man’s warm penis, Kimberly said to himself, This is my prize, my candy. I love Rick, and I love doing this. I obviously love cock.
As the fantasy grew more intense, and as he got used to having Rick inside him, Kimberly’s feminine desire to please Rick started to blossom. He made his mouth water to make the cock more slippery; he began taking it deeper; he started using his tongue. He noticed when Rick would suddenly gasp, or when the man’s hands or muscular thighs would tense up when he did something that must have felt really good. In response, he started to build a rhythm around these special touches. He even tried a little extra head bob with a tongue swirl that made Rick’s leg spasm – like a puppy when you scratch his tummy, Kimberly thought.
Kimberly was so proud that his man was so entranced, so intoxicated – with me! – that he didn’t realize that his extra effort was building up the intensity and volume of Rick’s impending orgasm. Rick was panting now, completely lost in sexual abandon.
"Oh, gawd, that's great, oh – yeah!" To Kimberly's dismay, his boyfriend started to orgasm, his hips bucking upward, great gobs of seed spurting into the boy’s mouth. It was thick and slimy, salty and sweet. He knew he had to take it all to avoid a big mess. He braced himself and held his head still to let the hot jism fill his mouth. He tried to swallow it all but some dribbled out around his lips and onto his chin.
Slowly the torrent of sperm subsided, but Kimberly wasn’t sure he could stop. He resumed his sucking, his tongue action, his swallowing until he had it all and Rick began to soften. When the man was finally spent, Kimberly was grateful for the tissue Karen gave him to wipe his mouth. Strangely, his first feeling afterward was not a boy's relief that his ordeal was over, but girlish pride that he had made his boyfriend so happy.
Yet the fantasy was over. The pantied youth sat up on the seat, ankles apart, knees together, arms crossed over his queasy stomach. Rick was still leaning back with eyes closed, his breathing slowly returning to normal. Finally, he sat up and arranged his clothes.
“Kimberly, I can’t believe how fantastic you were,” he said. “That was, so, so great – and you never did that before? Well, you must have been thinking about it for a while. I thought I was in heaven. That was the best, ever!” He leaned over and kissed the youth firmly on the cheek. "Let's go to the snack bar. You can go fix up your lipstick," he said.
He kept his arm around the stunned boy’s shoulders while they walked. On the way he whispered, "That was really great, Kimberly. It was awesome. I could tell you really got into that. You were almost as excited as I was!" Then he leaned down to softly kiss his date on the temple.
Kim's head spun. Did he act as if he enjoyed doing that? Like he was excited? He knew he had to do it, but why did his boyfriend – this guy, rather – think he liked and wanted to do it? He knew he had to do it, but did he have to do it so well? Had his actions betrayed feelings he didn't know he had? Is that why he felt glad that he had made his boyfriend happy, like a loving girlfriend would?
In the restroom, real girls came and went behind him or refreshed their makeup beside him, while Kim stared at himself in the big mirror, trying to accept what he had done. Here he was, a pretty boy in girl's clothes, rinsing another boy's seed off his teeth.
When he left the restroom, his “boyfriend” was waiting with his hands holding a tray of popcorn and sodas. Kim slipped his arm inside Rick's, feeling his hard triceps through his rough cotton shirt. He was glad for Rick’s strength and support as they went back to the car, because his knees were shaky and he felt a little faint.
Back in Chuck’s sedan, they shared their snacks and watched the second movie. With Rick’s strong arm around his shoulders, Kim rested his head against the young man's chest. Karen was right, Rick wasn’t physically aggressive once he had sex. And so. Kim could get what he wanted and expected from Rick: a warm, romantic feeling, the feeling a girl wants to have with her boyfriend. He felt at peace while they ate from the same box of popcorn. Strangely, he felt a sense of belonging to, and possessiveness toward his football hero, his Rick.
His romantic mood also made it easier to accept, and finally return, some soft kisses as the evening wore on. Earlier tonight it was gross to feel another boy's lips on his, but after their intimacy it seemed a small thing. Kim felt he couldn't refuse. It also seemed a sign of the older boy's gratitude, and by looking at it that way Kim soon got to enjoy it. After all, he was pretending they were boyfriend and girlfriend, and as they made out he willingly opened his lips to Rick's probing tongue.
But back at home after the boys dropped them off and Kimberly did give Rick that peck on the lips – plus some tongue – he felt terribly guilty about what he had done. He confessed to Karen that he "went down" on his date, that the older boy said he "loved cock."
Instead of offering her brother sympathy, Karen made it worse. She said he really didn't have to do that and that a girl always has the right to say no, and that the fact he did it meant he must have really wanted to do it all along – which means he probably does "love cock."
Her words, fueled by her guilt at enabling her brother’s humiliation yet by echoing what his date had said, hurt the boy deeply. It made Kim doubt his sanity – or at least his sexuality. He felt so bad that he vowed to never let Karen make him go out with a boy again. And as the last years of Karen's college career took more and more of her time, she moved into a dorm at school. Their c***dhood dress-up games ended after that night.
But Kim didn't grow any more macho than he was, and the cruel boys continued to tease him throughout high school. In the meantime, Karen's idea that Kim's first sexual experience would be as a girl rather than with a girl was having its effect. The locker room atmosphere became worse, as the memory of that night made Kim feel even more different from the other boys. He caught himself looking at their bodies, comparing them to his one-time partner. He remembered the taste of sperm. He couldn't even stop thinking how Rick had been his "boyfriend," the thought Karen had planted, which added to his humiliation.
Sometimes in the locker room the macho boys would talk about their exploits with girls. Since Kim had no experience with girls but did as Kimberly, he couldn't help but picture himself in these stories – as the girl. Over the weeks and months as each bragging jock told his story, in time Kim was forced to fantasize about having sex with every one of them, and doing for them what he did for Rick. He was mortified. He learned that he had given his boyfriend a "blow job," which, on a first date, was something only an "easy" girl would do, a girl that "loved cock." It stung to think that he was probably the subject of a boys' locker room story himself.
He was still attracted to girls, but his “boyfriend” was even invading his fantasy life. It would happen when he was imagining being alone with the prettiest girl in class, kissing her full lips, feeling her soft hair tied up with satin ribbons. He would unbutton her blouse, and cup her luscious breast in her lovely lace bra.
Then, at the peak of his excitement, he would wonder what it would feel like to be her, to experience Rick unbuttoning his blouse, to feel the man’s strong hands caressing his breasts in their satin cups, inching into his bra to play with his puffy nipples. Imagining he was the girl in his own fantasy made him feel more disgusted with himself. He felt branded inside for making that one mistake, for being so good at playing dress-up that he had to suck a cock.
So, one Saturday when Kim was fifteen and Karen was in college, Karen got him to go on a double date with her current boyfriend, Chuck, who was a senior at their school, and his best friend and teammate on the football team, Rick.
She styled Kim’s longish hair, and dressed him in pink control panties and a matching A-cup bra, which she filled with little silicone inserts she called "boy cheaters." Then she had him put on a tight white midriff top, plaid miniskirt, anklets, and flats. Kim's pulse raced as he looked in the mirror. The short skirt and bare midriff made him feel very sexy. The cheaters even had subtle nipples that pushed through the top, giving him a realistic feminine look.
“Oh gosh, Karen, I love the outfit,” he gushed.
“Well, the true test of a girl's outfit was whether her date likes it,” Karen replied. “Don’t worry, though. Rick will love it when he sees the young, fresh, female Kimberly.”
As they waited for their dates, Kim's mother told them to have fun and be careful. Karen convinced her that it was just for laughs, and was going to be a very casual movie date. She promised to watch Kim like a hawk, and make sure "nothing happened." The nervous boy assumed she meant that there would be no kissing – and that was fine with him!
Looking over her pretty little boy, Kim's mother smiled lovingly and said, "Kim, you would have made a lovely girl. I never realized just how beautiful my younger daughter Kimberly truly is!" Kim's heart skipped a beat at her sweet words. That's just how he felt, beautiful.
He hoped his date would think he was beautiful, too, and he could completely fool the boy into believing he was a real girl. Kim imagined that the boy would want to hold hands in the theater, and maybe try to put his arm around the pretty boy. Kim wasn’t sure he would allow that, but really looked forward to their goodbye. He hoped he would excite the boy enough so he would want to kiss him. Kim didn’t actually want to be kissed; he just wanted the boy to want to kiss him. Kim figured he would let the boy kiss him on the cheek, or maybe he’d be brave enough to give the boy a quick peck on the lips if he was nice. Then once he was safe inside afterward, he expected to get a good laugh at the boy’s expense, thinking how the guy would be falling in love with his feminine image, never knowing Kimberly was really a boy!
Right on time, the doorbell rung when the boys arrived. Rick was several inches taller than Kim, had a broad chest and strong arms, and seemed very polite. Karen introduced him as Kimberly, and he was excited at the attention and flattery the young man paid him. Especially since Rick was the type of macho guy who tormented him at school. Kim marveled how a boy's attitude was so much different toward him when the boy thought a he was a she. This wasn't so bad, being a girl, he thought. Kim felt butterflies inside as the young man firmly took his slender hand and led him to the back seat of the car where he would soon learn that being a girl is more than being worshipped from afar.
During the ride to the movie, Karen and the guys mostly talked about the big game last week, and it seemed that Chuck had thrown the pass and Rick made the catch to score the winning touchdown. Kim really didn’t care, but played along with Karen’s subtle encouragement on how to act like a girl and made sure he showed the proper amount of enthusiasm. He was afraid he went a little overboard in his gushing praise, calling Rick his “football hero,” but Karen seemed delighted. He assumed she was pleased with his performance.
It was when the car turned into a drive-in theater that Kim got the first indication their sweet double date was more dangerous than he had imagined it would be. As soon as they parked, Karen slid over to get cozy with Chuck. She leaned her head on his shoulder, blocking Kim’s view, so Kim had to move next to Rick to see the screen. Instantly the man’s arm was over and around Kim’s shoulders, cradling the boy’s elbow in his large hand and pulling him close to his muscular chest.
Kim had imagined that Rick would be like the boys his own age who would slowly and clumsily try to sneak his arm around the girl in a crowded theater. Now he immediately found himself in the arms of creature very unfamiliar to him, an adult male, in the semi-privacy of the back seat of a large sedan. The heat of Rick’s body, his musky aftershave, his possessive attitude toward his feminine companion put the boy on edge.
Things were pretty cool that way for a while, but began to heat up when Karen and Chuck started making out in the front seat. Kim was shocked at how blatant they were. He knew Rick had to be getting ideas of his own about his date. And it wasn’t long until the man reached his free hand across Kim’s face and caressed the boy’s smooth cheek. He turned Kim’s head toward him – Kim didn’t realize why but cooperated and looked in Rick’s eyes – and then it happened.
His first kiss. He was shocked and tried to not tremble. Rick’s hard lips and trace of stubble were so strange. He couldn’t help but feel anguish that he should be kissing a girl, instead of being the girl. He was also afraid that Rick would somehow be able to tell from kissing that he wasn’t a girl. He had to act like it was normal for him to kiss a boy, and that he wanted it and liked it. The problem was he didn’t know how to kiss. He had been prepared for a quick goodnight kiss at the end of the evening, but suddenly had to deal with Rick as he hungrily worked his way across the sissy’s painted lips. Kim tried to keep calm and relax his lips a bit, pretending he wasn’t terrified by Rick’s aggressive intensity.
Kim saw a movement in the corner of his eye and in the nick of time stopped Rick’s hand from grabbing his padded chest. Without missing a beat, Rick put his hand on Kim’s thigh. His powerful hand began caressing the soft naked flesh, pushing his skirt back inch by inch. Kim understood how vulnerable a girl in a skirt must feel, but felt it had to be even worse being a boy in a skirt. He pressed his knees together and pushed Rick’s hand away again, and again, but Rick persisted.
Karen and Chuck had slid down so Karen couldn’t see them. Their noises from the front seat made it clear they were past the kissing stage. Chuck had to be sucking her nipples, and judging by her moans, Karen loved it. Kim knew that Rick had to be getting frustrated with him, with his friend being so successful. Finally, after pushing Rick’s hand away for about the twelfth time, Rick blurted out, “C’mon, Kimberly! What’s the problem?”
Picking up on the tension in the back seat, Karen’s head popped up. Kim was right; Karen’s blouse was open and she was fastening her front-close bra. She quickly arranged her breasts and buttoned her blouse.
“Hey, Kimberly, I think we need to go to the ladies’ room, little sister. Hmmm?” Her tone made it clear it was not a request. “Chuck, Rick, we’ll be back in just a bit.”
Desperate to get away from Rick and glad to be rescued, Kim happily agreed. Karen pulled him along by the hand in a stony silence. He was planning to tell Karen how upset he was to be forced into this embarrassing and potentially dangerous situation, but when they got to the restroom Karen laid into her little “sister.”
“Kimberly, you are totally embarrassing me! You’re acting like some stuck-up little prude! You know, little sis, Rick has certain expectations. He’s a college senior, after all. There’s going to be trouble if you’re not nice to him. He knows you’re still in high school but you don’t want him to find out you’re just a sophomore, do you?”
She was talking to Kim like he was really a girl!
“But I am a sophomore, Karen – hey, wait a minute.” He realized something else was going on here. “What does that have to do with it? What did you tell him about me?!”
Karen leaned in with one leg out, hand on her hip. “Kimberly, sweetie, do you really think he’d go out with a fifteen-year-old? I told him there’s two years between us, not four, which makes you s*******n and a senior. And to make certain he’d take you out, I mentioned that you don’t know much about football, but you do like football players – a lot. I said you like jocks.”
Kim was stunned. Rick not only thought Kimberly was a real girl, but an experienced, horny high school senior who goes for jocks – they type of boys who despise him! And by following Karen’s prompting on the drive, Kim had played the role without knowing it, increasing Rick’s “expectations.”
Clutching his purse in front of him in shaking hands, Kim whispered, “Oh, Karen, I'm scared. I just thought we would cuddle. What should I do?"
Karen looked into her sissy brother's pretty face. He looked like a frightened doe, with big eyes and long lashes coated with mascara. She though what a poor excuse for a boy he was, nothing like the chiseled young men that waited for them back in the car. They would never think of putting on a bra and falsies, panties and a skirt, and get in the back seat of a car to cuddle with a horny guy, to see what it's like to be a girl.
She knew the date was her idea, but the fact that Kim was willing and eager to go along with it made her think that maybe he deserved anything that happened to him tonight. But she couldn’t let him get hurt, and knew there was only one way for him to keep his secret. It also dawned that this casual date was turning into a greater test than expected of her theory about Kim’s sexuality, and a way to see just how far he’ll go as Kimberly.
Karen knew Kim had no experience with girls, so she decided that his first experience with sex would be as a girl – with a boy – and it would be tonight.
In a soothing tone she explained her plan. "Kimberly, you need to understand that he's not trying to please you, just get you hot enough to please him. If you don't want him to touch you, you have to take the initiative and touch him. Make him happy, and he'll leave you alone afterwards." Somewhat sarcastically she added, "Then you two can cuddle."
"Touch him? Make him happy? What do you mean?" Kim looked confused.
"Back in the car, when he reaches for you, just take his hands away and reach for his pants. Start rubbing him there, you know, stroking it. He'll probably come in his pants and you'll be done."
Kim’s eyes popped out in horror. "Oh my god! Make a boy come? No. NO! I couldn't do that! I'd rather die first!"
"You won't die, probably,” Karen smirked, “but if he discovers your itty-bitty secret, he's going to get really, really mad. I’m sure he won’t get physical, but you can’t stop him from spreading the news about you all over town. I'm sure the boys in your school will be very understanding about your little hobby. Think how popular you’ll be! I bet they'll all want a special date with little Kimberly!"
Thinking about the cruel boys in school made Kim go white. He'd be branded for life if this got out. They would beat him up, or even worse they might force him to do things he didn't want to think about it. He might as well die, for the humiliation he would face. He reasoned that maybe Karen was right.
"So just, sort of stroke him, in his pants?" Kim asked meekly.
"I'm sure you know how to do that, little sister," Karen laughed. "You know what feels good for a boy. Here," she said, handing Kim some tissues. "In case any gets on you, you can wipe up."
Kim felt nauseous. "Can't we just leave? Please?!"
"No! Now do what I say, or he won't stop trying to undress you," Karen retorted. She looked into her brother's deep blue eyes and softened her tone. "Kimberly, I'm sorry. But trust me, everything will be fine if you take control. Every girl has to do it for a boy sometime, and tonight it's your turn. Just remember, he's excited because he thinks you're a girl, so be a girl. You're a girl and he's your boyfriend. And you’re a lucky girl! All the other girls are so jealous of you dating a college man. Right? Adopt that mentality and you'll do just great. C'mon, let's go back. You boyfriend is waiting for you."
Kim’s heart began racing when he opened the car door and saw Rick’s arm stretched across the back of the seat waiting to engulf him. Forcing a sweet smile, the pretty boy slid across the back seat until their hips and legs touched, when he was quickly enfolded in both of the man’s strong arms. Kim felt himself being turned toward Rick, who leaned in and nuzzled the boy’s neck with his raspy cheek.
“Feeling better now?” he whispered, obviously expecting that Kimberly’s sister had straightened her out.
“Uh huh,” the youth murmured. Kim’s hands came to rest on the man’s biceps. He squeezed the muscles, and felt the force he had to control, the anger he had to avoid.
“You like muscles, I hear,” Rick said.
Kim tipped his head up to respond to Rick’s question. “Uh huh,” he began to say, but his voice was smothered by Rick’s impatient kiss. Then Rick’s free arm moved, and Kim felt pressure on his chest. Rick’s palm had pushed against his padding; if he squeezed, he would instantly know the truth. Kim had to take control – now!
He forced a smile and moved the hand away. "I'm sorry, Rick. I get a little tender there, y'know, at that time of the month," he whispered with a pleading smile. Rick’s chest deflated. Then Kim did something he never imagined he would do. He tenderly kissed Rick right on the lips. Then, as Karen had instructed him, he reached across with his left hand and laid it on the older boy's crotch. He felt the bulky, coiled manhood start to awaken at his touch. His eyes grew wide.
"Hey, now that's better, honey," Rick hoarsely whispered. “I see you like what you found.”
He pulled back a little, letting Kim’s head rest on the man’s upper chest, tipped down. Now Kim was forced to watch himself slowly rubbing the man’s groin, rather awkwardly, with his palm, trying to not actually handle it with his fingers. He almost felt like crying as it stretched out to point straight at him. Rick moaned with pleasure. Although Kim was disgusted at the chore he was performing, he figured he had better make Rick feel good to get this over with as quickly as possible.
Kim wondered what a girl would do at a time like this, and figured a girl would respond to her boyfriend's enjoyment by getting into the act. A girl would think this was great and do something like – he reached his hand down between the man's legs to feel the shape of his weighty testicles, caressing them with his fingertips. He moved up to check the result – oh, my! – then caressed the lengthening tool with his fingers, tracing the outline of the older boy's excitement with his fingernails. Forgetting himself, Kim became hypnotized by its growing size and firmness. He gave it a squeeze at the root, then a few more, moving up toward the head. He wondered how it could still fit inside his date's increasingly tight pants.
"Hey, you're really into this," Rick whispered, giving Kim a quick peck on the cheek. “I know what you want.” Then, as if it was a prearranged signal, he called to his friend in the front seat, "Say, Chuck, I think it's your turn to, uh, go for some soda and popcorn." He sounded insincere, as if this was a signal between them.
"Sure thing, buddy,” Chuck quickly answered. “C'mon, Karen. I want to check out their arcade, too."
Karen was nervous about leaving Kim alone with an aggressive guy like Rick, but decided that their absence might spare him some embarrassment while he brings his date to orgasm. "Cool!" she relied. "Let's go!"
"B-but..." Kim stuttered and he started to sit up to stop Karen, but couldn’t move. Rick's arm had a vice-tight grip around the little transvestite’s shoulders, while his other hand had quickly moved to hold Kim’s forearm steady, keeping his pretty date’s hand gripping the bulge in his pants. Kim's heart leaped into his throat. This wasn't the plan! He was trapped!
As she slid over to the driver’s door, Karen was dying of curiosity to see what was happening in the back seat. "I guess we'll be a while. Have fun, you two!" she chimed, turning around. She had expected to see Kim facing forward and awkwardly reaching sideways across Rick’s lap, and was shocked to see how affectionate toward Rick he looked, nestling in the man’s arms. Also, he didn’t seem at all upset to be left alone with Rick, because he didn’t sit up or make any move to stop her. He didn’t seem embarrassed to be playing with Rick’s package either, because he didn’t move his hand the slightest when she turned around.
Kim was really getting into this, she thought, not knowing her brother was being held motionless. Maybe this proves he’s really gay, she mused, and his true nature is just coming out. Maybe I’m doing him a favor by getting him into boys. But a doubt still lingered in her mind – it was too dark to be sure, but was that a look of fear in his pretty eyes?
Chuck was calling her to come along, so she absolved herself of all guilt for whatever may happen to her brother, blaming him for being such a sissy. Then the car door slammed, leaving Kim alone to deal with a man with an erection.
"Alright! Now we have some privacy. Let's try this," Rick said, loosening his belt. Kim was terrified just by being alone with his date, and the guy was already undressing! The boy’s heart was racing and his head started to pound in panic.
"Unzip me," Rick ordered. The pantied boy didn't know what to do except play along. Caught up in the demands of his assumed role, he submissively obeyed. He managed to unbutton the waistband, slowly pulled the zipper down, and opened Rick's pants. Kim watched in awe as the young man pulled his cock out through the fly in his boxer shorts, revealing his arousal in the dim light. Kim couldn’t take his eyes off his date’s manhood. He became dizzy with fear and thought he might pass out.
Seeing Rick’s hard-on was a revelation to Kim. So, this is what men are like, what the boys at school are like when they get hard, he thought. He felt jealous; he was puny compared to them, but more importantly the sight crystallized his fear of them. If they found out about tonight, his life would be hell. Earlier he had imagined this date would be on his terms, but now it was on their terms – all the boys that had teased him. Pleasuring Rick would be like paying homage to all the locker room studs. But Kim knew he had no choice now; to complete his chore he had to actually touch it.
"Go ahead, Kimberly, I know you want it," the young man said. Almost in a trance, Kim reached over to take the naked flesh with both hands. His hands encircled the shaft, and he was surprised at how big a man’s cock actually got when aroused, as every girl discovers at her first encounter with one. The sissy boy slowly began squeezing, fondling, stroking it with his soft hands. He had done this to himself a few times, and now felt disgusted and humiliated to be doing another boy’s dirty work.
Yet as the older male grunted with pleasure, Kim began to understand the power a girl has over a boy. He figured Rick would like it if he quickened the pace a little. He felt a bead of moisture on its tip, and rolled it around the head with his thumb. He smiled at the man’s moan.
"That's nice, Kimberly, you sure know what you’re doing. Now, go down," Rick whispered.
"Go down? What...?" Kim wondered what he was doing wrong.
Rick chuckled. "Go down. You know, use your mouth, darlin'."
Kim was shocked at the suggestion. "I don't know... I never tried that before. I…I don't think so," he said timidly. He hoped Rick would understand and back off. Yet he knew it was something girls did for their boyfriends. His “boyfriend” thought he "wanted it." Would he act out of character if he didn't "go down"? Would Rick get suspicious?
"You never? I thought that’s what you wanted,” Rick insisted, his eyes locked on Kim’s eyes. “I can’t believe you’re a senior and you haven’t done that yet. C’mon, Kimberly, you’ll be so awesome. You’re such a loving person. And I really like you too, Kimberly. You're really special. You'll like it, too. All girls like it, especially when they swallow. That’s best for me, and it won't mess your clothes up that way, either. Chuck says your sister does it for him – don't you want to be like big sister? Come on, I can tell you'll be great! You obviously love cock."
Kim was following along but was mortified at Rick’s last words. Just because as a boy he knew what felt good, he had inadvertently made Rick think he “loved cock” so much that he wanted to “go down” on one – but never in his life had the boy even imagined such a thing. Yet now it was a reality. The notion was worse than the most terrifying nightmare Kim had ever had. But Rick had established his expectations and Kim would have to submit.
Kim felt sick to his stomach, but strange thoughts came into his head, alien thoughts for a boy. If girls like it, how bad could it be? Would I really be good at it, like he said? What does it taste like? But Kim's boy-self fought back against this bizarre temptation.
"No, not tonight. I'm sorry, maybe next time," he pleaded.
“Oh, c’mon, Kimberly,” Rick was getting upset. “You can’t leave me this way. You were so hot for it a minute ago, I thought that’s what you wanted all along!” He was definitely angry now. “Kimberly, you were the one that started stroking me! Don’t be a tease!”
Kim felt pressured to do it to keep his secret, but also had to admit that Rick was right. This was his own fault for trying to fool the young man, and he was just getting what he deserved. Rick didn’t deserve to be teased and then denied his pleasure; he couldn’t help his feelings, his desires. His very masculinity demanded from Kim a feminine response. If it was something a girl would do in this situation, he had to do it too.
The pounding in Kimberly’s head became worse, and a spasm of nausea twisted his stomach. He felt like a trap door had opened under him and he was falling, hopeless. He realized that he really had no choice and that in a matter of moments….
The thought of having a cock in his mouth was so frightening that Kim's mind would not accept that he would be used in this way. Recoiling from the shame, he wished that just for tonight he wasn’t himself – and then something clicked in his mind.
This whole scenario was too horrible, too shameful to be happening to Kim, so it wasn't. It was happening to Kimberly. Which meant it wasn’t humiliating. Rick would never get turned on by a boy, only by a girl. This macho football player would never pull it out for a boy, only for a girl. Kim knew that he would never want to do this, but a girl would – so I’m a girl, Kimberly thought. I’m Rick’s girlfriend.
In the back of his mind, he knew he was pretending, but once this switch flipped in his mind, Kimberly experienced new emotions welling up within him. He was overwhelmed by a sense of obligation to Rick, and that he shouldn’t be a tease. Then he felt like he was melting inside, that his body and mind were surrendering to the older boy's sexual power. He became weak in the presence of true virility, yet at the same time was flattered and excited. It seemed a privilege to be responsible for Rick's arousal, to experience this intimacy as a girl. It was like he was a secret agent, learning what only girls learn about boys, back seats, and hard-ons. A wave of tenderness and caring toward his date came over Kimberly. He wanted to be every bit the girl he had to be to make his boyfriend happy.
As his thoughts focused, Kimberly noticed that he had never let go of Rick’s penis and never stopped caressing it. And now it was time to go down on his date.
“Don’t tell my sister, okay?” he pleaded, looking up at Rick. “I don’t want my mom to find out.”
“Oh, I won’t tell a soul, Kimmy,” Rick lied, grinning, knowing he had made another conquest.
Rick guided him down off the seat. The skirted boy’s bare knees hit the carpet and his dream of being Kimberly really began. Like in a dream, he was perfectly calm in spite of his terror. He found it interesting that the man was basically fully clothed – easier to cover himself up if we get caught, Kimberly thought. It was strangely exciting to think that, on the other hand, anyone would know why he was on the floor of the car, kneeling between Rick’s legs.
The older male’s hard-on was inches from his face. Rick’s manhood seemed so enormous up close, standing upright like a proud soldier. It loomed even larger as Kimberly leaned forward, then it disappeared as he tipped it down and opened his mouth wide. Kimberly’s eyes focused on the boyish blue plaid of Rick’s boxers as he lowered his head, as the underside first brushed against his tongue, as his lips closed around the warm cockhead.
To take the very core of Rick’s masculinity inside his own body stunned the boy. He felt utterly defeated, yet warm feelings toward his conqueror rushed up within him. He felt Rick playing with his hair, tucking some stray locks behind his ears. He glanced up at the man; their eyes met. “Good girl,” Rick murmured. Realizing he wouldn’t be groped while he was doing this, accepting that Rick saw only a girl, Kimberly began to feel confident, in control. I’m a girl, I’m a girl, I’m a pretty girl, floated through his mind.
This idea freed Kimberly to fulfill his role more completely – to add a new dimension to the dream. Subconsciously, acting like a girl who felt affection or even passion toward her man was the best way to deny the shame he really felt. It also sparked a fantasy in the sissy’s mind. This wasn’t ****, it was romance. Kimmy did this for Rick every week. They had been dating for months, this is how she held on to her college man, her football hero, and all the other girls at school were jealous because Rick was such a jock and so well-endowed. Moving his mouth around the man’s warm penis, Kimberly said to himself, This is my prize, my candy. I love Rick, and I love doing this. I obviously love cock.
As the fantasy grew more intense, and as he got used to having Rick inside him, Kimberly’s feminine desire to please Rick started to blossom. He made his mouth water to make the cock more slippery; he began taking it deeper; he started using his tongue. He noticed when Rick would suddenly gasp, or when the man’s hands or muscular thighs would tense up when he did something that must have felt really good. In response, he started to build a rhythm around these special touches. He even tried a little extra head bob with a tongue swirl that made Rick’s leg spasm – like a puppy when you scratch his tummy, Kimberly thought.
Kimberly was so proud that his man was so entranced, so intoxicated – with me! – that he didn’t realize that his extra effort was building up the intensity and volume of Rick’s impending orgasm. Rick was panting now, completely lost in sexual abandon.
"Oh, gawd, that's great, oh – yeah!" To Kimberly's dismay, his boyfriend started to orgasm, his hips bucking upward, great gobs of seed spurting into the boy’s mouth. It was thick and slimy, salty and sweet. He knew he had to take it all to avoid a big mess. He braced himself and held his head still to let the hot jism fill his mouth. He tried to swallow it all but some dribbled out around his lips and onto his chin.
Slowly the torrent of sperm subsided, but Kimberly wasn’t sure he could stop. He resumed his sucking, his tongue action, his swallowing until he had it all and Rick began to soften. When the man was finally spent, Kimberly was grateful for the tissue Karen gave him to wipe his mouth. Strangely, his first feeling afterward was not a boy's relief that his ordeal was over, but girlish pride that he had made his boyfriend so happy.
Yet the fantasy was over. The pantied youth sat up on the seat, ankles apart, knees together, arms crossed over his queasy stomach. Rick was still leaning back with eyes closed, his breathing slowly returning to normal. Finally, he sat up and arranged his clothes.
“Kimberly, I can’t believe how fantastic you were,” he said. “That was, so, so great – and you never did that before? Well, you must have been thinking about it for a while. I thought I was in heaven. That was the best, ever!” He leaned over and kissed the youth firmly on the cheek. "Let's go to the snack bar. You can go fix up your lipstick," he said.
He kept his arm around the stunned boy’s shoulders while they walked. On the way he whispered, "That was really great, Kimberly. It was awesome. I could tell you really got into that. You were almost as excited as I was!" Then he leaned down to softly kiss his date on the temple.
Kim's head spun. Did he act as if he enjoyed doing that? Like he was excited? He knew he had to do it, but why did his boyfriend – this guy, rather – think he liked and wanted to do it? He knew he had to do it, but did he have to do it so well? Had his actions betrayed feelings he didn't know he had? Is that why he felt glad that he had made his boyfriend happy, like a loving girlfriend would?
In the restroom, real girls came and went behind him or refreshed their makeup beside him, while Kim stared at himself in the big mirror, trying to accept what he had done. Here he was, a pretty boy in girl's clothes, rinsing another boy's seed off his teeth.
When he left the restroom, his “boyfriend” was waiting with his hands holding a tray of popcorn and sodas. Kim slipped his arm inside Rick's, feeling his hard triceps through his rough cotton shirt. He was glad for Rick’s strength and support as they went back to the car, because his knees were shaky and he felt a little faint.
Back in Chuck’s sedan, they shared their snacks and watched the second movie. With Rick’s strong arm around his shoulders, Kim rested his head against the young man's chest. Karen was right, Rick wasn’t physically aggressive once he had sex. And so. Kim could get what he wanted and expected from Rick: a warm, romantic feeling, the feeling a girl wants to have with her boyfriend. He felt at peace while they ate from the same box of popcorn. Strangely, he felt a sense of belonging to, and possessiveness toward his football hero, his Rick.
His romantic mood also made it easier to accept, and finally return, some soft kisses as the evening wore on. Earlier tonight it was gross to feel another boy's lips on his, but after their intimacy it seemed a small thing. Kim felt he couldn't refuse. It also seemed a sign of the older boy's gratitude, and by looking at it that way Kim soon got to enjoy it. After all, he was pretending they were boyfriend and girlfriend, and as they made out he willingly opened his lips to Rick's probing tongue.
But back at home after the boys dropped them off and Kimberly did give Rick that peck on the lips – plus some tongue – he felt terribly guilty about what he had done. He confessed to Karen that he "went down" on his date, that the older boy said he "loved cock."
Instead of offering her brother sympathy, Karen made it worse. She said he really didn't have to do that and that a girl always has the right to say no, and that the fact he did it meant he must have really wanted to do it all along – which means he probably does "love cock."
Her words, fueled by her guilt at enabling her brother’s humiliation yet by echoing what his date had said, hurt the boy deeply. It made Kim doubt his sanity – or at least his sexuality. He felt so bad that he vowed to never let Karen make him go out with a boy again. And as the last years of Karen's college career took more and more of her time, she moved into a dorm at school. Their c***dhood dress-up games ended after that night.
But Kim didn't grow any more macho than he was, and the cruel boys continued to tease him throughout high school. In the meantime, Karen's idea that Kim's first sexual experience would be as a girl rather than with a girl was having its effect. The locker room atmosphere became worse, as the memory of that night made Kim feel even more different from the other boys. He caught himself looking at their bodies, comparing them to his one-time partner. He remembered the taste of sperm. He couldn't even stop thinking how Rick had been his "boyfriend," the thought Karen had planted, which added to his humiliation.
Sometimes in the locker room the macho boys would talk about their exploits with girls. Since Kim had no experience with girls but did as Kimberly, he couldn't help but picture himself in these stories – as the girl. Over the weeks and months as each bragging jock told his story, in time Kim was forced to fantasize about having sex with every one of them, and doing for them what he did for Rick. He was mortified. He learned that he had given his boyfriend a "blow job," which, on a first date, was something only an "easy" girl would do, a girl that "loved cock." It stung to think that he was probably the subject of a boys' locker room story himself.
He was still attracted to girls, but his “boyfriend” was even invading his fantasy life. It would happen when he was imagining being alone with the prettiest girl in class, kissing her full lips, feeling her soft hair tied up with satin ribbons. He would unbutton her blouse, and cup her luscious breast in her lovely lace bra.
Then, at the peak of his excitement, he would wonder what it would feel like to be her, to experience Rick unbuttoning his blouse, to feel the man’s strong hands caressing his breasts in their satin cups, inching into his bra to play with his puffy nipples. Imagining he was the girl in his own fantasy made him feel more disgusted with himself. He felt branded inside for making that one mistake, for being so good at playing dress-up that he had to suck a cock.
1 year ago
