Girls will be boys, and boys will be girls.
It's a mixed up, muddled up, shook up world,
except for Lola.
Lola had just turned fourteen. Her party had been a roaring success, as far as she was concerned that is. All of her friends had been invited. She had received a ton of presents. Everyone had watched movies, talked, and played games. Several kids had sneaked away to play spin the bottle. Lola had even been able to sneak away and take a turn. She had kissed Jacob and Troy before she had to go back to being the hostess of her party. It had been the best day of her life. What she didn't know was that her life was about to change.
A baby screamed and the exhausted mother was delighted. The young doctor held the squalling infant and gave it a quick examination. Everything looked fine. She said, "Congratulations. It looks like you have a fine healthy boy, uh, what?" Then there was the longest silence.
Finally the new mother couldn't stand it. "What? What?" She nearly screamed, "My baby! Is my baby all right?"
The doctor turned to the mother. "Your baby looks healthy."
She let out a held breath. "My baby is healthy. He's okay then?"
The doctor paused. "I don't know if he's a he or a she." The young mother looked confused. "Your baby has a penis and a vagina." The world went black for the new mother.
Luckily, for this family, the young doctor was fresh from a progressive medical school and had studied the latest literature on intersex children, hermaphrodites. In the past, these unfortunates were turned into girls because the surgery was simple; lop off the penis. But studies of these children had discovered that they usually were born genetically a boy or a girl. That preference had little to do with which physical attribute was dominant, penis or vagina, but was inherent in the genetic structure of the child, especially inside the brain. About age five, the child's brain would change for one of several times and express whether he was a he or she was a she. Then during puberty, the human brain completely rearranges itself into a male brain or a female brain. The decision was permanent and was locked in genetically. So the doctor advised the new parents to wait until the child was at least five before they decided on surgery.
Of course, in our society, it isn't possible to have a sexless or bi-sex child. So the family raised her as a girl, Lola. They even worked with the psychiatrist to best help Lola grow up without the feeling of being 'wrong' that many intersex children have. During her fifth year, the psychiatrist administered a whole battery of tests to Lola. The results were conclusive. Lola's brain was functionally and structurally a girl's brain. There was the tricky issue that her male sex organs were dominant.
It isn't often appreciated that hermaphrodites are almost always born with one complete set of sex organs and the other only a partial set. The embryonic tissue can form one complete set of reproductive organs. So if they form ovaries, they will not form testes. In this case, the 'penis' is usually just a greatly enlarged clitoris, rather than a fully functioning penis. In Lola's case she had a full set of male organs including the testes and a vagina, but she did not have a uterus or ovaries. If they did surgery to remove all of the male sexual equipment, she would be able to have sex, but never conceive. It would also be difficult, if not impossible, for her to achieve orgasm, as she would be missing a clitoris as well.
Because she lacked ovaries and therefore the hormones to make her a woman, she would have to use artificial hormones from the beginning of puberty. The psychiatrist wondered what would happen if a girl had male sex organs. He persuaded the parents not to force Lola into surgery, leaving her the option ‘later in life,’ even though his own research indicated her choice was already made. He would be able to write a professional article about this case. The family assumed he had their best interest at heart and trusted his judgment.
It was the day after her fourteenth birthday that the psychiatrist explained all of the facets of her uniqueness and some of the decisions she would have to face to Lola. She had started the hormone therapy two years before. She was growing into a lovely young woman, her breasts swelling, her hips were becoming rounded. Her face retained the softness of a female and her voice would not change. The hormones had slowed but not stopped the development of her penis which had started to grow as well.
After he had finished, he asked her for questions. Lola was a little dizzy. She always knew she was a little different, but this was hard to get her head around. “Am I a boy or girl?” she asked.
“You are a girl. You’ll always think of yourself as a girl,” he said. “And the hormone therapy will make your body into that of a woman.”
“Then why didn’t you cut it off?” she asked. “Like you said you could have.”
“We don’t really know if you would be better off. Lola, I want you to understand you aren’t less than your friends, you are more. You can be a girl and you can also be a little bit like a boy if you want. This is going to seem confusing for a while. What I want you to realize is that everyone your age is confused about their sexuality. It is quite normal. Don’t think you are confused because you have both options. You simply will have more choices but everyone your age will be confused,” he said paternalistically.
Lola was confused, but no more so than any other fourteen-year-old. She kept clear in her mind that she was special, and her parents reinforced that idea, not just different, but better; she could chose either sex.
She was fourteen and a half when someone other than her family and doctors found out about her special character. Her family had tried to raise her like any other girl, with some special limits. When her parents finally allowed her a sleepover with her best friend Caitlyn, there was a faint feeling of uneasiness. They had put her off for several years. It wasn’t until they were certain she knew the risk of others discovering her difference that they relented. It had taking months of begging, crying, and wheedling on the part of Lola.
The evening had been perfect for Lola. She and Caitlyn had eaten pizza, watched romantic movies, and talked forever. Caitlyn was supposed to sleep in the guest room, but they had decided to sleep together. After everyone else was asleep, Caitlyn had snuck into Lola’s room. They had gotten into bed together. It was only then that Lola realized that something had changed. She looked at Caitlyn in her skimpy pajamas and she felt her penis swell for the first time. She had never had this happen before. She knew she was able to be a boy sexually if she wanted and had been convinced that this made her special. But to have it happen so unexpectedly…
The light was out in order to not attract attention but bright moonlight poured in through the window. They looked at each other and giggled. Lola screwed up her courage and asked Caitlyn, “Are you my best friend?”
“Of course, silly. I am your b-f-f just like you are mine,” she answered.
“What if I had the biggest secret in the world? So big, you would have to promise never to tell anyone,” Lola said.
“Of course I’d do that,” Caitlyn said sobering a little.
“And what if you had to promise not to think I’m different or weird,” Lola asked.
Caitlyn was realizing that this was something serious. Luckily for Lola, she had picked a very special best friend forever. Caitlyn said, “Lola, you are my best friend. I’d never tell your secrets and I’d never hate on you because you are different.”
“I mean, like really different,” Lola said.
“Cross my heart,” Caitlyn answered.
Lola did one of the hardest things she had ever done. “I was born different,” she said.
“You mean, like retarded?”
“No, nothing like that. I’m not missing anything. I’ve got something extra,” Lola said.
“Like a hump?” Caitlyn asked.
“Well, sort of. You want me to show you?” Lola asked. Caitlyn held her breath and nodded. Lola took a deep breath, then pulled down her pajama bottoms. Her penis flopped out.
“You’re a boy!” Caitlyn nearly screamed.
“Shhhh. No I’m not,” Lola said.
“But…”
“Give me your hand,” Lola ordered. Caitlyn reached over. Lola took her hand and held it between her legs. “I’ve got a vagina just like a girl.”
Caitlyn would normally have felt awkward having her hand on another girl’s vagina. In this case, it seemed a relief. It felt just like her own pussy, which she had been feeling for two years and she knew how a vagina was supposed to feel.
“I’m a girl. They did all sorts of tests and I’m a girl. I just have something extra,” Lola said.
“So you’re a girl, have a puss, but you have a…” as her hand moved up from Lola’s vagina and over her penis. Caitlyn took the opportunity to feel it. After all, she was a girl so it wasn’t really like a boy’s. Except that it swelled in her hand, just like a boy’s would have. “Cool,” she said feeling it pulse with life and grow. Caitlyn stroked it softly watching it grow in the silvered light from the moon. “God, that is weird,” she said.
But from her friend’s voice, Lola knew she didn’t mean a bad weird, but a strange maybe cool weird. “It’s never done this before. It feels kind of good,” Lola said.
“Don’t you touch yourself?” Caitlyn asked.
“No. Do you?”
“Sure. I’ve been doing it for two years. You have to try it,” she said. Caitlyn thought about how some of their friends were practicing together because they couldn’t have boyfriends yet. Practicing with Lola would be even better. Then she giggled. She thought, ‘My best friend has a cock and a pussy.’ “I bet you could do yourself,” she said.
“What?” Lola asked.
“Sex. You know, do yourself.” Caitlyn decided to show her. She started to bend her penis back towards her vagina.
“Ouch,” Lola cried out.
“Sorry,” Caitlyn said. “Maybe when it’s not hard. You know, when it’s soft you could bend it around and do it to yourself. God, wouldn’t that be something.”
Lola had her doubts. That had hurt when Caitlyn had bent her cock. Caitlyn was still stroking her cock which quickly dispelled the hurt feelings. It was feeling quite good. She started wondering about what Caitlyn had said, touching herself. Maybe she would have to try it.
Caitlyn was looking at her friend’s cock. She wasn’t a boy, right? So it would be alright if she pressed against it. ‘It really is okay to practice with a girl,’ Caitlyn thought, ‘since so many of their friends had done it.’ “Can I try something?” she asked.
Lola was a little worried after the last idea Caitlyn had, but she said, “Okay.”
Caitlyn squirmed out of her pajama bottoms and moved over to Lola. She held Lola’s cock and pressed her pussy against it. It wasn’t working very well. Lola was bewildered wondering what Caitlyn was trying to do. Caitlyn pressed Lola onto her back and moved over her. She slid her pussy over her cock. They both felt something quite good was happening to them. “Oh,” they chorused in pleasure. Caitlyn was quickly wet with arousal. It felt good to be rubbing against something hard, even better than when she rubbed herself. ‘It wasn’t really sex if she was doing it with a girl,’ Caitlyn thought as the knob of Lola’s cock caught in the opening of her pussy. Caitlyn pushed back and felt the hard shaft forcing her open. Her pussy lips flared open to accept the invader into her body for the first time. There was a momentary pain as the cock slid into her fully, but that was quickly overcome by the intensity of the pleasure of being filled. She bottomed out, full of cock and ground her clitoris against Lola.
Lola was surprised when Caitlyn began rubbing herself over her girl cock. But she was even more surprised when she felt her cock enter her friend’s pussy. Surprised, but not displeased. In fact, it was one of the best things she had even experienced. Well, she had always been told she had the option of doing it either way. This way certainly felt good.
Caitlyn ground down onto Lola’s cock, driving both girls crazy with delight. She lifted up and began fucking her girlfriend with her pussy. Lola’s cock drove up into her repeatedly, over and over, filling her. Caitlyn had never felt anything so wonderful. ‘This is what it feels like to be a woman,’ she said to herself.
Caitlyn was swept up in the pleasure of sex, pounding down and being filled. She felt her own climax rising. Once more, she thrust her girlfriend’s cock up inside her, and then one last time… The world exploded around her as waves of pleasure filled her. It had never been this good before when she touched herself. Her body trembled with the last dregs of pleasure as she felt the strength flee her body
Caitlyn collapsed onto Lola. Lola felt spasms in her balls and thrust up into her friend. Her orgasm waned after a few spurts. Her hormone therapy left her balls underdeveloped and only a trickle of cum was ejected, but it didn’t matter to Lola. She had her first orgasm and it was incredible. Caitlyn rolled to the side. “You are special.”
They both giggled. “Can we do that again sometime?”
“Oh, yes.”
They fell asleep in each others' arms.
In the morning, Lola’s mother looked into the room. She saw the girls sleeping in the same bed and was appalled. Not because they had sex, the idea never entered her head. They were both girls after all, but because she knew that Caitlyn would learn of Lola’s difference. It was her worst fear. “Lola.”
Lola woke, brushing the sleep from her eyes. She saw her mother standing in her door. There was a worried look on her face. Then the girl realized that Caitlyn was still sleeping next to her. She was going to be in trouble. “Yes?”
“Please get dressed and both of you come to breakfast. Hurry, please,” her mother told her.
“Yes, Mom,” Lola said. The door closed. ‘Oh God. Mom is going to be mad.’ “Caitlyn,” she said shaking her friend. Caitlyn woke up slowly. “My mom found us.”
“So,” Caitlyn said.
“What if she thinks we’ve, you know?” Lola asked. Caitlyn’s eyes opened wide. “Come on. We have to get dressed.”
The girls bounced out of bed and quickly dressed. Caitlyn stared as Lola put on her panties, carefully tucking the cock between her legs. “Wow, is that how you do it?”
“Yeah. Otherwise it can stick out and make clothes look wrong,” Lola said.
“Do you think we’re in trouble?” Caitlyn asked.
“I don’t know. She said we should come to breakfast, so maybe not,” Lola said. “Come on, let’s hurry.”
Mrs. R was putting the bacon in the pan wondering how she was going to tackle the subject of Lola’s special nature. Was it possible that the girls shared a bed and Caitlyn didn’t know? The fact that Caitlyn hadn’t run screaming from the house argued for that. She was mixing up the pancake batter when the girls stormed into the kitchen.
“Hi, Mom.”
“Good morning, Mrs. R,” Caitlyn said.
“Pour some juice,” Mrs. R said. “Three, your father has already left for work.”
The girls helped get the table set and ready while Mrs. R prepared breakfast. At one point, Caitlyn had taken some dishes out and Mrs. R asked, “Did Caitlyn discover your special nature?”
“Yeah, but…” Lola started to answer. But as Caitlyn returned Mrs. R hushed her and turned back to the stove.
As they sat down to breakfast there was the usual small talk about the girls enjoying the sleepover. Mrs. R wondered how to broach the topic. She settled on the direct. “Caitlyn, last night you found out about Lola being special.”
Caitlyn took another mouthful of pancakes, “Yeah, cool,” she answered around the pancakes.
“I want you to understand a few things. Lola is a girl despite her extra appendage.” Caitlyn nodded. Mrs. R continued, “And we have been very careful because some people wouldn’t understand.”
“Yeah, I know. Lola and I talked last night. I thought about that.” She turned to Lola, “Like Trish, she’d be a total bitch.” Then back to Mrs. R, “Sorry. I mean I totally understand. Lola and I are best friends, Mrs. R. I’d never do something to hurt her. I won’t tell anybody unless Lola says I can first.”
Mrs. R breathed a deep sigh of relief. It seemed that Caitlyn did understand. She just hoped this would work out. It wasn’t possible to keep it hidden forever, but the longer the better she thought. “Thank you, Caitlyn. It is important to me and to Lola.”
“No problem, Mrs. R,” Caitlyn said around more pancakes.
After breakfast the girls helped clean up. Mrs. R told the girls she was going shopping and would be gone a couple of hours. She suggested they take showers while she was gone. The girls ran upstairs to Lola’s room. Once there, Caitlyn said, “Let’s take a shower together.”
Lola agreed, “Okay. We can use my parent’s shower. It’s big enough for two.” They waited for Mrs. R to leave before stripping and heading for the shower. Once in the shower, Caitlyn asked, “Would you like me to wash you?”
At first, Lola was nonplussed. But in the night something had awakened in her. Caitlyn’s question brought it to the fore. She felt little butterflies in her stomach, nice ones. “Yes,” she said, not sure why she liked the idea. Caitlyn grabbed the soap and lathered her hands. She stood behind Lola and started washing her back. It was a very nice girl’s back. Lola had a cute little butt and Caitlyn liked running her hands over it. Lola was enjoying the sensuality of having another’s hands stroking her. At the same time, she felt a little nervous; this was all so new.
Caitlyn lathered more soap onto her hands. She pressed against Lola, which brought a gasp from the girl. It was exciting to feel her friend’s skin rubbing against hers. Caitlyn’s hands started on her shoulders and washed in circles, down until they were rubbing Lola’s tender young breasts. Her nipples erected. Lola then felt this thing that was so new to her. Her little cock started to grow. She looked down to see it pulsing and standing up. Caitlyn, behind her, couldn’t see the effect she was having. Her hands continued washing the girl, lower and lower. When they got to Lola’s cock, it was standing hard and straight. Caitlyn was surprised, “Oh.” She wrapped her hand around it and slowly stroked it. Caitlyn thought about the prior night, how good it felt to have Lola fucking her. And Lola was a girl so it wasn’t wrong to have sex with her like it would be with a boy. Her mother had warned her about boys. Caitlyn couldn’t wait. “Let’s get dry and go to your room.”
Lola was surprised, “But we aren’t done.”
“We can finish later, please,” begged Caitlyn.
“Okay,” acceded Lola. They turned off the water and dried off quickly. Caitlyn pulled the girl to her room and lay back on her bed, legs spread wide.
“Lola, do me again,” Caitlyn asked.
Lola looked at her friend and she knew what she wanted her to do. Her cock was hard. She crawled between her legs. Caitlyn’s hand grasped her cock and led it to her pussy. Lola lay on Caitlyn and her cock nestled into her girlfriend’s pussy, already wet with arousal. Lola pushed and her cock found its way into Caitlyn. Caitlyn moaned as her pussy flowered open around Lola’s cock. Lola was again caught up in the glorious feeling of her cock buried in Caitlyn’s warm pussy. Lola began fucking her best friend.
Their small breasts brushed against each other as the girls fucked. Caitlyn felt a strange warmth suffusing her body. The warmth crested and her body tingled… then she climaxed, moaning from the new sensations coursing through her body. Lola felt Caitlyn’s pussy spasm on her cock and it drove her over the top her own climax bursting inside her. The hormones used to make her a woman interfered with the development of the testes and she wasn’t able to produce sperm. Her cock spasmed, but nothing was produced. She didn’t notice at all as the orgasm swept over her as a pleasing lassitude filled her.
The girls lay next to each other in bed. “Lola,” Caitlyn said. “You are my best friend.”
Lola smiled, “You are my best friend. Do you want to do this again?”
Caitlyn smiled, “Yeah. How about every day?” They laughed together.
So Lola learned to use her cock and Caitlyn was a very happy girl because she was sexually fulfilled and yet didn’t have to put out for any boys. If she got too wound up, she would just stop by Lola’s house and they would ‘take care of it.’ They were both happy with the situation.
The only quandary was that Lola was a girl and she wanted a boyfriend too. She had continued developing with the help of the therapy. She was growing into a very attractive young woman. When she and Caitlyn turned sixteen their parents told them they could date. Mrs. R was again worried, but she couldn’t put Lola in a cage and protect her forever. She did suggest double dating with Caitlyn which Caitlyn’s mom also thought was a good idea.
At school, Caitlyn and Lola had been working on two boys, Danny and Patrick. Danny had just gotten his drivers license. The girls made the boys think they had a great idea; why not a double date with Danny driving. The big event, dinner and a movie, was a hit. Both guys got big kisses at the end of the date, enough to leave them with blue balls until they got home and furiously jacked off. The couples became a foursome.
Danny complained a few times to Caitlyn. He wanted to get her alone for some serious foreplay. She always made it plain that she felt comfortable with Lola, and don’t worry, I will do anything with her there as I would without her there. Danny wasn’t sure exactly what that meant, but in his jack off fantasies, it meant she was going to put out.
They had been dating for about a month when the boys decided it was time to try to up the ante. They took the girls to a drive-in movie. They parked in the back row. Patrick had scored some Coors from his older brother, who had given him a rubber and instructions on making a girl go crazy; kiss her neck. That was his whole secret. It was no wonder that Patrick’s older brother had as little experience as Patrick. Patrick broke out the cans of Coors. The four of them drank a couple cans as the movie played.
They were all feeling mellow when Danny turned to Caitlyn and began kissing her. Patrick followed suit and the windows quickly steamed up, not that they cared. The boys had talked earlier and decided tonight was the night to go for it. Danny worked his hand up Caitlyn’s side until it was touching her breast. She turned so that her tit filled his hand. She moaned as he softly stroked it. Patrick heard the moan and lifted his hand up to Lola’s wonderfully formed breast. It filled his hand. She pressed against his hand. He was in Heaven, feeling a real live girl’s tit. He caressed it slowly and softly. Lola moaned in his mouth as they kissed.
The Plan was working. Their hands dipped down to the girl’s knees, then worked north. They were brushed away. They tried again, to be repulsed again. Once more, the hands sallied forth to be met by a strong defense. “Stop it.”
“But Caitlyn…” he whined.
“Stop it, or you’ll have to take us home,” Caitlyn said. Patrick said nothing letting his partner carry the battle.
“But Caitlyn, I just want to…”
She cut him off, “You just want to have sex.”
The word hung in the air. There was nothing to say since that is exactly what the boys wanted. If it wasn’t for Lola’s unique world view, this would never have happened, but she was different, in a good way. She turned to Patrick, “Would you let me do you?”
Caitlyn said, “Yeah, would you let me do you?” to Danny.
He didn’t quite get it. “How can you do me?”
Patrick was much more the worldly one having read all of his older brother’s collection of magazines. “In the butt.” Danny’s head nearly came off it swiveled so fast. “I read about it in Penthouse Letters. Girls can do guys in the butt.”
“That’s disgusting,” Danny said.
Caitlyn crossed her arms over her chest, “That’s settled then. You no, me no.”
Desperate, Danny turned to Caitlyn ready to beg, saw the hard look in her eye, and looked back to Patrick hoping for a miracle. “But that don’t make sense. How can a girl, you know?”
“Like with her finger, and once in a letter the girl used her vibrator on the guy,” Patrick said.
“In his butt?”
“Yeah. He said he liked it,” Patrick said. “At least in the letter he said that.”
“That’s sick,” Danny said.
“I’m just telling you what it said in Penthouse Letters,” Patrick said defensively.
The girls were starting to giggle at the effect they had on poor Danny and Patrick. Danny was shook up by the idea of anyone sticking something up his butt. The mood had been totally broken. Danny started the car and drove them to Lola’s house. Caitlyn had been staying at Lola’s after their dates, the better for the girls to work off any lingering tension. Lola’s girl cock would make them dreamy and satisfied.
The girls lay together basking in the afterglow of sex. “Patrick sure seemed to know about butt sex. Danny was all like no way, but Patrick didn’t say he wouldn’t do it.” Caitlyn lifted herself on one elbow and looked at Lola. “Would you really do him?”
“I don’t know,” Lola answered. “I’ve never had sex with a boy. He’d want to do me then.” They were quiet for a little, then Lola asked, “Do you like having my thing inside you?”
“Yeah,” Caitlyn answered.
“Maybe I should let Patrick do me,” Lola said.
“Hey. I’m going to be jealous if you get laid first,” Caitlyn said laughing. Their two years of fucking somehow didn’t count. It was who got the first boy that mattered.
Caitlyn stopped by Powell’s bookstore on the way to Lola’s house. Once in Lola’s room, Caitlyn pulled out the book, The ABC’s of Anal Sex.
“Oh my God. How did you get that?” Lola asked.
“I bought it,” Caitlyn said. Lola looked at her in disbelief. “I did. It was kind of funny, you know, walking up to the front with it but the girl at the checkout didn’t say a thing. Just made me pay for it.” Caitlyn opened the book. “Look, here it tells you everything you need to know. It even has a chapter for women doing men.”
“No,” Lola said.
“Yes,” Caitlyn responded. “Look.” She held open the book to a page with a drawing of a woman behind a man. She was wearing a strap on cock with which she was fucking him. “You don’t need the belt,” Caitlyn said laughing. They started reading together.
“KY?”
“Yeah, but you can use other stuff.”
Giggling as they scanned the chapter, their reading was punctuated with the occasional, “Oh my God!”
At the end of the chapter Caitlyn turned to Lola, “So, are you going to do it?”
Lola thought for a while, “I’d like to know what it feels like…”
Caitlyn closed the book, “Well, if he’s willing to let you maybe he deserves to be the first. But I’m going to be jealous.” They both laughed.
At school that week, Lola worked up the courage to ask Patrick if he wanted to come to her house on Saturday. Her parents were going to be at a company affair and she would have the house to herself. Patrick didn’t know that part when he accepted. He thought they were going to be studying. Well, he certainly was going to learn.
The girls got together Friday night to battle plan the next evening. “What are we going to tell him?” Caitlyn asked.
“We?” Lola asked. “What do you mean we?”
“Lola. I have to be here. I mean, you don’t know how he’s going to act when he finds out about, you know,” Caitlyn said. “I will be here to support you, just in case he gets weird.”
Lola looked worried. “I hadn’t thought about that. You think he’ll get weird?”
“No, not if we do it right. We just have to have him prepared,” Caitlyn argued. Lola nodded. “Okay, here’s my plan…” Caitlyn said conspiratorially.
Patrick showed up right after dinner as instructed. He had flowers his mother had helped him pick out. Caitlyn opened the door to Patrick’s surprise and disappointment. “Oh, hi Caitlyn.”
“Don’t look so disappointed,” she said as she grabbed his arm and pulled him in. “Lola,” she shouted. “Patrick’s here and he brought flowers.”
Patrick blushed.
The girls had spent hours deciding which outfit Lola should wear. Should it be sexy? Or sweet? Or slutty? Or dominating? They settled on a one-piece low cut tight dress that highlighted her curves and presented her breasts for display. Her youthful breasts didn’t need a bra and she wasn’t wearing one, making the presentation all the more visible. Patrick’s eyes bugged out as Lola, on cue, swept into the room.
“Hi, Patrick,” she said coquettishly. “Are those for me?”
“Uh, yes.”
“I’ll put them in water,” Lola, bent over to smell the flowers giving him a view of her breasts almost to the nipples, relieved him of the flowers, kissed him with a kiss which promised many things, and swept from the room in her best Hollywood diva imitation. Caitlyn followed her. Patrick was left standing in the front room, bouncing from foot to foot.
Lola swept back into the front room carrying the flowers in her Mother’s best crystal vase. “They’re beautiful,” she said looking at Patrick with a sexy allure. Lola led Patrick into the dining room where Caitlyn had the book open on the table.
Patrick’s eyes bugged open when he saw the drawing. He looked up at Caitlyn and Lola who simply smiled in return. Caitlyn patted a chair, “Have a seat.”
Patrick wasn’t sure if he should. But the picture had aroused conflicting emotions, fear and desire, a dangerous combination in a teenage boy. And like all teenage boys, desire was more powerful than fear. He sat. Lola slid into the chair on his other side. Patrick looked down at the book. It was the picture showing a man on his knees and a woman behind him, her strap on dildo entering his ass. The woman had a devilish look on her face. Patrick gulped and looked at Caitlyn and Lola. “I… I… I…”
Caitlyn smiled, “You, you, you, what? Cat got your tongue?”
“I didn’t think…” Patrick was having trouble finishing his sentences.
Caitlyn cut to the chase. “Do you want to have sex with Lola?” which caused both Patrick and Lola to blush. They looked at each other and formed a bond as they saw they both felt the same way; scared but excited.
“Yeah,” Patrick said.
“Are you willing to try it our way first?” Caitlyn asked.
Patrick paused, first to consider did he want to let the girls fuck him in the ass? Then to consider what did she mean by our way? Would both of them be involved? About the first, his mind was made up rather quickly. He would do it. He wanted so badly to lose his virginity that anything was bearable. But the second idea really intrigued him. “What do you mean both of you?”
“I’m going to be there,” Caitlyn said.
Patrick assumed he was going to have sex with both girls. Hell, they could have told him they were going to beat him with whips and he would have said yes. “Okay,” he said barely able to restrain his excitement.
Caitlyn jumped up and grabbed his hand. “Come on,” she said leading him and Lola to her room. Once in the room, their plan continued. Lola stepped into his arms and they kissed. Caitlyn came up behind him and started to undress him. Lola continued kissing him as Caitlyn stripped off his clothes. It was a bit awkward and would have been funny except that the sensual atmosphere overrode any humor. Once he was naked, Lola released him. He was a bit embarrassed standing with his erect cock pulsing in front of the two girls. It was time for the next step.
Caitlyn began undressing. Patrick couldn’t take his eyes from her as she sensuously shed her clothes. Lola was also stripping, but slowly and not provocatively. As Caitlyn dropped her panties and stood before Patrick like a Greek Goddess, she led him to the bed. “Get on you hands and knees,” she said. Patrick looked at the girls; Lola was still wearing her panties, before he got on the bed. Caitlyn climbed in front of Patrick and spread her legs. He stared. He was mesmerized by seeing a real live pussy for the first time. Caitlyn shared a look with Lola, ‘See, I told you he’d be putty in our hands.’ Lola dropped her panties her cock springing up, fully erect. She got on the bed behind Patrick. They had a tube of lubricant already on the bed. Lola lathered her cock, then spread some of the cold lube on Patrick’s ass.
Caitlyn was ready for the moment. As Patrick was about to lift his head to protest, Caitlyn grabbed his head and pulled it into her pussy, “Eat me,” she commanded him.
He had thought of this so many times as he read his brother’s magazines, going down on a woman. His nose filled with the scent of woman. His tongue lanced out and he tasted Caitlyn. The smell of aroused woman drove Patrick into sexual overload. He barely felt it as Lola used a finger to loosen his back entrance, then a second. It began to feel good, her finger massaging his prostate, mixed as it was in his mind with the pleasure of tasting a woman for the first time. Patrick licked and kissed Caitlyn’s pussy as Lola lined up behind him. She pushed, was resisted, then pushed again as her girl cock slid into his tight ass.
Patrick knew this is what the girls were going to do and had expected it to hurt and it was uncomfortable at first. But that was replaced by pleasure as her cock slid along his prostate and the experience of eating Caitlyn all melding in his mind as a moment of exquisite pleasure.
Caitlyn was enjoying having Patrick lick her pussy. It wasn’t something she and Lola did; after all, they were both girls. She shared a look with Lola who had started fucking the boy. Lola loved the feel of her cock sliding into the boy. She was making love with a boy. Patrick was on the inside of a girl sandwich and loving it, eating Caitlyn as Lola fucked him.
Lola came first, her climax erupting from deep within, sating her as nothing before had ever done. She pulled out of Patrick, her cock withering, shiny with the lubricant. Caitlyn was next, clenching her thighs around Patrick’s head as her orgasm surged through her body.
She relaxed, finally releasing his head as she slumped back onto the bed. Patrick licked his lips, staring at Caitlyn’s wet and red pussy. He had done it, had given a girl an orgasm. He continued looking at Caitlyn, admiring her naked body, bemused and happy. Caitlyn was the first to recover and looked meaningfully at Lola. Lola lay face down on the bed.
Caitlyn caught Patrick’s eye. “Ready?”
He nodded.
Caitlyn sat up as did Patrick. He was half hard. She stroked his cock bringing him quickly to full hardness and driving him a little crazy with desire. “It’s her first time,” Caitlyn said. Patrick nodded again. Caitlyn put some of the lube on Patrick’s cock and led him between Lola’s spread legs. As he got in position, Lola rose up to meet him. Caitlyn led his cock to her opening. She seated his cock at her virgin entrance, “Be gentle,” she instructed him. It all went so quickly that Patrick was at the portal of Heaven before he even knew what was happening.
Patrick pushed gently, felt Lola open to accept him, he pushed a little more and entered her. Lola squeaked as she felt him broach her opening for the first time. Now she knew she was truly a woman.
Patrick was in Heaven. He was having sex with a girl. It was worth anything to feel his cock buried in a girl’s pussy. He bottomed out, his loins up against Lola’s soft little butt. He pulled back, watching his cock emerge from her pussy to reverse and thrust it back into her. All of those sessions of jerking off trying to imagine what it was like were nothing compared to the actuality. He closed his eyes and lost himself in the physical sensations emanating from his loins. He picked up speed as he approached his climax. Caitlyn had her hand on her clitoris, matching the thrusts of Patrick, imaging that he was thrusting into her. Closer he came... Then it hit him, the overwhelming sensations of orgasm and he pumped himself into Lola’s sweet pussy. She felt him filling her and she also climaxed, a small one.
Patrick emptied himself and fell back onto the bed. Lola fell forward, drained. Caitlyn furiously rubbed herself and joined the lovers in climax. The room was filled with the sound of heavy breathing as the three teenagers all recovered.
It was at this point that Patrick noticed something dark between Lola’s spread thighs. He looked closer, shook his head to clear it and looked again. It was definitely what he thought it was. “She’s a boy,” he said distraught.
Caitlyn was caught off guard. She had been ready for the moment but it took her a minute to compose herself after her orgasm. “Don’t be stupid.”
Stupefied, Patrick looked at her, “But…”
“Didn’t you just make love to her?” Caitlyn asked him. He nodded. “Then she’s a girl you idiot.”
Patrick looked back at Lola who had turned to face him now that the cat was out of the bag, so to speak. He stared at her cock.
“Show him,” Caitlyn said. Lola lifted her cock to display her puss so recently fucked that it was glistening with his cum. “See, it’s your stuff in her pussy.”
Patrick was on overload. He looked back and forth between the two girls. Lola was all girl from the waist up and from behind. But damn if that didn’t look like a cock. “It looks like a cock,” was all he could say.
That made Caitlyn laugh which caused Lola to laugh. “It is.” Lola moved over to Patrick arranging herself so that all of her feminine charms were on display and her extra equipment was hidden. Patrick looked at her, naked and beautiful, her wondrous breasts there for his delight.
“I don’t understand,” he said.
Caitlyn patted his thigh as Lola snuggled into his side. “It’s okay,” Caitlyn said. “Lola is a girl. She was born a girl: she thinks like a girl, she feels like a girl, she will always be a girl. But when she was born she had a little extra thing. It doesn’t make her a boy. It’s just something extra.” Caitlyn hit him while he was down. “You do want to have more sex?”
Lola’s hand had strayed to his cock and she was lightly playing with it.
“Yeah,” Patrick replied brightly. Caitlyn held his eye forcing him to consider. He did. It was a bit strange, but he would get laid. And Lola was a hot babe. The guys in school would be totally envious. And no one else would know about her… cock. There, he said it, cock. She was a girl. His own cock was growing as he thought of fucking Lola again.
Caitlyn saw him growing and smiled. “I bet that’s the answer,” she said.
Lola squeezed his rapidly growing cock, “I hope so.”
Patrick smiled. He was going to get laid by a beautiful girl. He kissed Lola and she returned it with passion.
Caitlyn’s hand stole down to her puss as Lola turned over and Patrick lined up with her pussy. ‘They are a cute couple,’ she thought as her finger took her to her climax.
After Patrick left, Lola brought Caitlyn to several thunderous climaxes as thanks for her plan. She had a boyfriend who didn’t mind her difference. Life looked brilliant to Lola.
Having a boyfriend opened up the world to Lola. Other boys seemed to notice her more. It gave her confidence to flirt. And the hormones continued to do their job; Lola became a babe. She was also smart and popular. After she tired of Patrick, the varsity quarterback asked her out. He was a major hottie. Lola and Caitlyn talked for hours trying to decide whether to accept or not. Fooling Patrick, thankful as he was for any sex, would be majorly different from Brad, the football hero. He had been laid, and everyone knew about it since it had been in the middle of a party. He had fucked Tabitha, the head cheerleader who was drunk at the time, in the living room as a party was going full swing. Thirty people had witnessed the whole thing. It was Lola who made the decision; yes.
In much the same was as they had fooled Patrick, they fooled Brad. When the whole play started, Brad was sure he was about to get a double, that both girls wanted him, the football stud. The girls got him stripped and Lola fucked him. Then he fucked her. The three were lying in the afterglow when Brad asked Lola if she would do him again. He had liked it. After Lola had fucked his tight little ass several times that night, it wasn’t a problem that she had the extra equipment. Brad loved it. They would sixty-nine. Then Lola would fuck him and he’d fuck her.
There was an unexpected benefit after Lola and Brad broke up. Lola went through several boys on the football team. Then she ran into her first boy who threatened to out her to the whole school. Lola was in a panic. Caitlyn saved the day. She reminded the guy that several of the football team had dated Lola. If he tried to go public they would all swear that Lola was all girl, as would Caitlyn. They would say that he was queer and couldn’t get it up and with the varsity quarterback and half the football team against him, who would believe him. He deflated like a blow up doll with its plug pulled. All he could hear in his mind was the whole school calling him fag.
Caitlyn decided he should get the treatment as punishment. He tried everything to get the girls to change their minds but the threat of being a pariah and called 'queer' hung over his head. The only way for him to avoid the dreaded tag was to take it up the butt. Lola loved sliding her girl cock into his tight boy butt. But a funny thing happened. The boy wound up cumming while Lola fucked him. The girls realized he loved it. They encouraged him to return the favor and fuck Lola’s pussy. The short version, he became Lola’s most devoted boyfriend. She learned a valuable lesson on dominating boys. A lesson she would apply very well later in life.
Her senior year, Lola was the hit of the school for it was known she put out. Since Lola had no ovaries, she didn't worry about getting pregnant, a great treat for the boys who could cum anywhere anytime. Caitlyn was the ice queen, she never put out, at least to the guys. The girls were jealous of Lola’s popularity and the boys simply lusted, wishing they were one of the lucky guys to date Lola.
It was near the end of her senior year that Lola decided what she was going to do with her life. She had come to love power, dominating power over boys, power for its own sake.
She plotted out her life. She had her fill of a new boyfriend every two weeks. That was so high school. She would be much more circumspect, maybe even a little prudish from now on. She would find a man she could dominate; she was going to have the balls in the family. She would get a law degree. The law was the path to power. Her future was limitless. Maybe someday she could be President. She needed to leave her current life behind. Too many people knew Lola and there was a certain reputation attached to the name after a band had written a song about an evening she and Caitlyn had danced at a local club together and then met the band members at their hotel. The last thing she did as she left for college was to change her name. The whole world was before her now to be conquered with her big balls. Some day the world would know her by her new name, Hillary.
Lola
I met her in a club down in old Soho
where you drink champagne and it tastes just like Coke Cola
C-O-L-A Cola.
She walked up to me and she asked me to dance.
I asked her her name and in a dark brown voice she said, "Lola"
L-O-L-A Lola, lo lo lo Lola
Well, I'm not the world's most physical guy,
but when she squeezed me tight she nearly broke my spine
Oh my Lola, lo lo lo Lola
Well, I'm not dumb but I can't understand
why she walked like a woman and talked like a man
Oh my Lola, lo lo lo Lola, lo lo lo Lola
Well, we drank champagne and danced all night,
under electric candlelight,
she picked me up and sat me on her knee,
She said, "Little boy won't you come home with me?"
Well, I'm not the world's most passionate guy,
but when I looked in her eyes,
Well I almost fell for my Lola,
Lo lo lo Lola, lo lo lo Lola
Lola, lo lo lo Lola, lo lo lo Lola
I pushed her away. I walked to the door.
I fell to the floor. I got down on my knees.
I looked at her, and she at me.
Well that's the way that I want it to stay.
And I always want it to be that way for my Lola.
Lo lo lo Lola.
Girls will be boys, and boys will be girls.
It's a mixed up, muddled up, shook up world,
except my Lola. Lo lo lo Lola.
Well I left home just a week ago,
and I never ever kissed a woman before,
Lola smiled and took me by the hand,
she said, "Little boy, gonna make you a man."
Well I'm not the world's most masculine man,
but I know what I am and I'm glad I’m a man,
so is Lola. Lo lo lo Lola. Lo lo lo Lola.
The Kinks, lyrics by Bill Clinton
p.s. If you're a liberal Democrat and are getting all, you know, because of Hillary, get over yourself. Jeez, even liberals should be able to laugh...
Did you like the story? Let me know what you thought. I answer all feedback. Please make sure your address is correct and you are set up to accept email from me:
Or you can e-mail me directly
The next story is Two Dykes and a Dude
Return to Gender Bender homepage
Copyright Rod O'Steele © 2006, 2007, 2010, 2011, 2012, 2013