Courting the Landlady’s Daughter 
By Suzanne High-Heels

Copyright © 2007 Suzanne High-Heels.

tv, humil, anal, oral, sissysex.

“All right, that concludes the lecture.” announced the teacher to the lecture hall. “Please remember that your first assignment is due at the end of next week.” His reminder fell upon the noise of disinterested students, who wanted to get out of there. Among them was Carl. He had at last begun his final year at university, but that wasn’t the only thing remarkable to have happened to him recently. Not so long ago, someone very special had come into his life. 
“Coming out onto the town on Saturday night, Carl?” asked his friend John. 
“Not this weekend, I’m going to be…busy.” said Carl with a smile.
“Oh, sorry, I forgot, that new girlfriend of yours, try not to do yourself an injury.” When Carl left the room, John turned to Vicki and Hailey, two of the girls from the class. “Does anyone know who this girl is?” he asked. 
“No.” replied Hailey. “He must be keeping her a secret.” 
“You never know, she may not even exist.“ said John mockingly. 
“John, that’s terrible.” snapped Vicki. “He’s found love with a girl and you make fun of him.”
“Oh sorry.” answered John sarcastically. 

Carl was in hurry to get home, he speedily made his way back to where he was staying for his final year, number 22 Green Lane. A small-detached house owned by the strict but loving Sophie Abbot. Her beautiful blond haired daughter Lucy, lives with her. She is Carl’s new girlfriend and the love of his life. To his amazement, Lucy revealed herself as a girl with a ‘dolly’ in her panties. She is a very attractive and feminine sissy. They have been lovers for only two weeks, but Carl felt more fulfilled with Lucy than with any previous lover, even though they had only gone as far as oral sex. Mrs. Abbot had also turned Carl into a sissy and gave him the name Gina. Now he has all the pleasures of being dressed as a female in soft, frilly clothing. He is enraptured by silky feminine feelings when Lucy is around. For university, Mrs. Abbot allows him to wear his male clothes, except for a pair of navy blue schoolgirl knickers he has to secretly wear. 

Upon entering the house, he was greeted by the sight of a maid’s uniform laid on the table next to the phone. An exquisite pair of black stilettos were standing elegantly next to the dress. A note on the dress read: ‘For sissy maid Gina.’ He knew these would have been left by Lucy to start some role-playing. He took the uniform and shoes up to his bedroom, changed out of his dull male clothes, slipped on a bra, changed his schoolgirl knickers for some black lacy ones, put on the uniform and shoes, then applied plenty of make-up, just as he had been shown by Mrs. Abbot. He minced his way down the stairs to the living room. Lucy was sitting in the chair by the window. She was wearing a breath taking shiny pvc mini dress with red five-inch spiky heeled shoes. She showed off her smooth legs by crossing one over the other. 
“Hello Gina, are you feeling OK?” asked Lucy.
“Yes madam.” he said going weak at the knees.
“You may start by giving my shoes a little lip service.”
“As you wish madam.” said Gina. He delicately moved over to Lucy with short sexy strides in his heels, bent down to the floor, and began to kiss Lucy’s sexy shoes. Gina enjoyed kissing pretty shoes, as did Lucy, the smoothness of the footwear, the smell of the leather and the gratification of the wearer. Having her shoes kissed made Lucy feel like a princess, she enjoyed the feeling of the shoe leather being pushed onto her feet by Gina’s lips. 
“Thank you Gina. You may now move onto me.” He moved on to Lucy’s face, stood up and began smooching her cheek. Lucy’s lips were next to receive the much-desired attention. The room echoed with the sexy sound of slurping between the two sissies mouths. “Perhaps madam would like some more intimate treatment?” suggested Gina. Lucy’s penis, now rock solid, eagerly awaited to be freed from the soft frilly knickers and receive its servicing. Lucy’s dress was flipped up and down came her knickers. Gina knelt down and hungrily licked her lips. “Ooh, thank you for the tasty treat madam.” said Gina. The naughty sissy opened his sinful mouth, ascending slowly onto Lucy’s stiff member. The anticipation reached incredible heights as she felt his breath on the tip of her penis. With all the excitement, they didn’t hear Mrs. Abbot come in the front door. 
“Goodness me, in the living room, whatever next?” said Mrs. Abbot with just a little humour in her voice. 
“We were just playing, Mummy.” giggled Lucy.
“Yes, I can see that. But you’ll have to stop now. Your cousin Victoria is coming over for a visit in about half an hour, so you two get dressed into something nice.” 
“But Mummy, I was just about to have my lollipop sucked.”
“You can have Gina suck your lollipop all you want later, right now I want you dressed in something nice for your cousin Victoria.”
“OK, Mummy.”
Lucy pulled up her knickers and excitedly took Gina by the hand and took him upstairs where they got dressed up. Lucy looked particularly cute and sexy. She was wearing her gorgeous red satin dress. It had white lace trim on the puffy sleeves and the skirt with pink satin ribbon bows on the bodice. She wore the dress with white frilly ankle socks and patent red Mary Janes. A large satin red bow decorated her beautiful long blond hair. Gina put on her schoolgirl summer dress with pelerine socks and pink stilettos.

Just after half past five, there was a knock at the door. 
“I’ll get it.” said Lucy. “Hi.” she greeted the person. “Come in.” Carl had already seen a few of Mrs. Abbot’s friends while he was fully dressed in girly attire so didn’t think too much about a visitor. He would change his mind however, as Lucy’s cousin was also Vicki from his class. He stood up in surprise when he realised who it was.
“Vicki, uh..I.” 
“Carl.” she said in disbelief. Her former boyfriend stood before her wearing a sissy pink gingham dress with a big floppy bow at the back. His pastel pink high heels also drew her attention. 
“I thought you might know each other.” grinned Mrs. Abbot. “After all you both study history at the local university right?” 
“Yes…we do.” answered Victoria.
“Sit down you two.” said Lucy. She pushed Carl down onto the middle of the sofa while she and Victoria sat at either side of him. As the two of them began chatting, Carl covered his face in shame. His girly antics would soon be the talk of the town, not to mention the university. 
“Oh stop crying Carl.” ordered Mrs. Abbot. “Victoria is a very nice girl, I don’t think she’ll give away your guilty secret.”
“No, of course not.” said Victoria with sincerity in her eyes. 
“Victoria’s been my special girlfriend since kindergarten.” piped up Lucy. “She used to dress me up in a dress and play high heels when we played house.” 
“You remember the time at my house, my sister caught you dressed as Tinkerbelle the fairy? I thought she’d die of laughing.” 
“He was a very effeminate boy as a child.” said Mrs. Abbot. “All the other boys wanted to go as ghosts and ghouls each Halloween but he always insisted on going as Minnie Mouse or the little mermaid.” laughed Mrs. Abbot. 

Later, in Lucy’s bedroom, Lucy, Gina and Victoria were playing little girls’ games. The twist was however, the games had been devised by the mischievously playful imagination of Lucy. They had tied a couple of pink bows in Victoria’s hair and dressed her in a sweet yellow dress, little white socks and black Mary Janes, just so she looked the part like they did. The first game they played was ’Guess whose.’ Quite a simple game where one person is blindfolded and has to guess who an item of clothing belongs to by having it gently rubbed in their face. Victoria was first to be ‘it’, she was blindfolded in Lucy’s pink pvc sleep mask and sat down while Lucy and Gina stepped out onto the landing to decide what to use. 
“What do you think that is?” asked Lucy as she brushed one of Gina’s frilly socks under her nose. 
“Mmm, something made from cotton, I think it’s a sock, not frilly like you were wearing so I think it’s one of Gina’s socks.
“Yes, your right.” said Gina, removing the blindfold from Victoria. “Gina, your next.” said Lucy cheerfully. Gina sat down, Lucy put the cool pvc sleeping mask on him. In the darkness, he could only hear Lucy and Victoria giggling quietly. It made him a little uneasy. They left the room, but soon came back. Someone was standing next to him, from that person came Lucy’s sexy voice. “What do you think this is Gina?” He felt something smooth and silky over his nose and mouth. He took in a deep breath. “Ahh, I love that smell.” said Gina. Lucy giggled with delight.
“Yes, you know it very well don’t you Gina darling?”
“They’re your panties Lucy.” he said. He felt the panties removed and Lucy kiss him sweetly on his lips. 
“Your right.” 
The next game was another of Lucy’s creations. ‘Don’t cum in Mummy’s slipper’. She took a pair of pink fluffy slippers out from the back of her wardrobe and explained the idea of the game to Gina. “Basically, one of us is Mummy who holds the right slipper, a sissy has the left slipper placed over her little lady and the other sissies attempt to make her cum within five minutes by kissing her, talking dirty or stripping off in front of her, but they’re not allowed to touch the slipper. If the sissy cums into the slipper, Mummy will give her a spanking. But if the sissy resists, Mummy will give her a loving kiss.” Victoria sat in the chair playing the part of Mummy as she obviously couldn’t play the part of a sissy. Lucy and Gina rolled a die to choose which one of them would have the slipper on their sissy clitty. Lucy won and chose Gina to be the victim. With his dress ruffled up and his panties around his ankles, Gina sat on the bed. Lucy placed the left fuzzy slipper onto his dolly. The slippers soft lining felt good brushing against his little princess, there were some crusty patches, evidence of past releases of cum into the slipper. Victoria began to time five minutes on her watch. Lucy wasted no time in getting started once Victoria said go. She started by slowly kissing Gina’s face and probing her own panties at the same time, making certain Gina knew what she was doing. “Do you like that Gina?” she asked before giving him another dose of kisses. Lucy then changed tack and slowly removed her party dress while standing in front of him. As Lucy danced in front of him in only her panties, socks and shoes, he glanced over at Victoria who was watching Lucy’s frolicking. She was holding the slipper in one hand and gently smoothing the sole over the other, occasionally smacking her hand with it. He could feel some cum building up inside his dolly, he tried to hold it back to avoid receiving a humiliating spanking from his former girlfriend. It wasn’t much use however because he could already feel pre cum building up. Lucy smothering his face with her sissy breasts didn’t help at all. “How about a satisfying ejaculation.” she whispered in his ear. “You know it’s what you want.” She then took to caressing her pantied bottom with her hands. And when that didn’t work, Lucy brought Victoria into play, engaging in a deep sissy-girl kiss. That was it. SPLOSH. The inside if the slipper was saturated with Gina’s love juices. Coming out of their exciting passion, Lucy and Victoria noticed Gina looking a little uncomfortable. “Have you cummed?” asked Lucy. Gina just nodded. Lucy gently took the cummed slipper from Gina’s spent wee wee. Strands of cum dropped from inside and landed on Gina’s leg. “That was a lot Gina. Here, wipe yourself down with this.” said Lucy giving her a couple of tissues. Lucy gave the slipper a quick clean out and left it to dry. “Right, over Mummy’s knee.” shouted Lucy.
“Come on Gina, I promise not too hard.” said Victoria. Gina bent over her lap with his bare bottom perilously exposed. Victoria swung the slipper through the air hitting poor Gina’s sensitive bottom.
“Oh.” cried Gina. “I thought you said you wouldn’t do it hard.”
“Well not TOO hard.” she continued. Hit after hit came from the fluffy slipper, until eventually she let him up. Gina began to rub his sore bottom. “When me and Lucy use to play that with a couple of other sissies from London, when they were getting spanked, they used to encourage me to hit as hard as possible.” 
“Let’s play mummies and babies now.” said Lucy. She placed two black and two pink marbles into a bag. “If you draw a black you’re a mummy and if you draw a pink your a baby.” Victoria was the first to choose and brought out a black marble. Gina picked out a pink, Lucy was also hoping for a pink but instead drew a black. 
“Ahh, I wanted to be a baby.” moaned Lucy. “Oh well. Come on Victoria lets get our mummies stuff on.” Lucy took out from the wardrobe two red rubber aprons and a couple of pairs of high-heeled pumps, a white and a black pair. Victoria and Lucy each took off their Mary Janes and slipped their feet into the stilettos. Lucy took the black pair and Victoria the white, then they put on the rubber aprons. “Now, where’s Gina’s outfit?” Lucy took a bag from her wardrobe and emptied it out onto the bed next to Gina. Darling satin pink bootees, a sweet baby bonnet, a pair of mittens and a white fluffy diaper. “All right Gina, time to get you out of your girls’ clothes and into your baby suit.” said Lucy. Gina sat and stared at the outfit. He’d never been dressed as a baby girl before, now it was about to happen, and would be dressed by his sissy girlfriend and his ex girlfriend. He felt a little vulnerable as he took off his party dress but the girls soon had him laid on the bed and diapered. It felt nice, even reassuringly comfortable as a matter of fact. The cool satin of the bootees and mittens felt good against his skin, when they slipped them onto his hands and feet. He sat up and Victoria tied the bonnet under his face. 
“Is that nice, Gina honey?” asked Lucy. Gina nodded.
“It feels good yes.”
“Shall we give baby Gina her bottle?” asked Victoria.
“Yes, come here Gina, I’ve prepared a nice drink of milk for you.” said Lucy as she sat down on her bed, and took her sissy penis out from her knickers. “Come and suck your bottle.” Gina crawled over to Lucy, he wrapped his lips around Lucy’s dolly, forming a moist seal as he moved down Lucy’s shaft. “Ah, yes, oh, that’s…it Gina. Suck it hard for maximum nourishment. 
“Wow, your quite good at this Gina.” cooed Victoria. “Of course she learned from you didn’t she?” she remarked, looking at Lucy. She was about ready to go.
“Mmmmm…mmmmmmmm.” moaned the two sissies. Gina felt Lucy’s sissy dairy begin to  pulsate, then his throat was coated with Lucy’s warm baby milk. He swallowed the whole lot, smiled at Lucy and said; 
“Thank you, Mummy.” 
“Just off to the little girls’ room.” announced Lucy. After visiting the toilet, Lucy was returning to her bedroom when she heard Victoria talking with Gina about his new life as a sissy. Lucy stopped and eavesdropped for a few moments. 
“I must say Carl, I would never have expected you to enjoy being a sissy.”
“I know, but I kind of like it. Dressing up and everything. And Lucy is amazing.”
“That’s not quite what I meant. A playboy like you, you’ll never be able to, you know, a real pussy again.”
“Oh I’m not bothered by that.”
“Really?”
“Yes. I mean, I haven’t really thought about it.” 
“Lucy can’t do everything a genuine girl can.”
“I know, but she can do much more that no other girl I have ever met can do. I suppose I might miss sex with a real girl eventually.”
“Yeah, I just don’t want you girls getting too serious then end up getting hurt. We had a great time though, didn’t we? In the first year of Uni.”
“I remember, Dr Thompson almost catching us having sex in the female toilets. It was such a thrill.” Lucy stood out on the landing a little saddened. 
“Gina, are you drifting away from me?” she thought.

The next day, what Gina had said was still playing on Lucy’s mind. So, around lunchtime, Lucy decided to do something that always makes her happy. Shoe shopping. Lucy is something of a regular in the female shoe and clothes shops in town. None of the staff in the stores have any idea about her little secret. The notion that Lucy wasn’t actually female would have seemed ridiculous to them, as she is one of their most feminine customers. Lucy looked around and decided she’d like to try a pair of orange high heels. Her favourite assistant, Brian the foot fetishist, was on hand to assist. 
“Would you take off my ankle boots please?” asked Lucy.
“Certainly madam.” Lucy usually wears socks when she shops for shoes to deliberately tease Brian. But today, Brian was in for a surprise. He’d always get a little closer than he should to the sexy female customers’ feet, and his face was within inches of Lucy’s boots as he gently unzipped them. Lucy of course played innocent and pretended she had no idea what was happening. When Brian removed the first boot, instead of finding a white sock preventing him from seeing Lucy’s foot, he found she was actually bare footed. He gasped in amazement and tried to keep calm. This wasn’t easy though having one of Lucy’s well-pedicured and perfect feet near him. He took her other boot off, his penis got harder when Lucy wiggled her toes. As Brian got his breath back, Lucy tried on the shoes.
“Perfect, I’ll take them.” she said. 

On the way home, Lucy was passing the food court in the shopping mall. She was surprised to see Carl in there, she thought he must be on his lunch break. She was about to go over when she saw Victoria sit down with him. They kissed sweetly on the lips. To everyone else in the mall it looked like two lovers meeting at dinnertime. Lucy felt angry. Instead of going over to them she went straight home to plot her revenge. 

Carl arrived home later and immediately transformed himself into Gina. Today he went for the sexier look of a young woman instead of putting on a little girl’s dress. A black mini dress with black stockings and red high heels. 
“Lucy.” he called. “Are you in there?”
“Yes Gina, come on in.” said Lucy, luring him into her bedroom. She was laid tantalisingly on her bed, wearing a schoolgirl’s shiny gymslip made from pvc. A pair of white socks and black pumps were on her feet complimenting her smooth, sexy legs.
“Oh, do you want to play naughty schoolgirl, Lucy?” asked Gina.
“Something like that.” answered Lucy. “Get into the panty bag, and take your clothes off first.” she said pointing at a silky pink bag on the floor. A little apprehensive he got into the bag. Inside were a few of Lucy’s and Mrs. Abbot’s dirty panties, stockings and bras. Lucy pulled and tied the drawstrings, sealing him inside. She began to roll him over the carpet, his body slithering around inside the bag and the dirty underwear pressing against his skin.
“Lucy, what are you doing?” he called from the bag.
“What were you doing with Victoria in the mall today?” 
“Talking to a friend, Lucy.”
“Liar.” she shouted, taking off one of her shoes. “You love her don’t you, not me.”
“No, I…” He tried to answer but Lucy had gone into a rage, she repeatedly landed blows on him with her shoe. Whack, whack, whack went the shoe. Eventually she stopped and burst into tears.
“You can stay in there with that dirty washing for all I care.” blurted Lucy. She lay down on her bed and quietly sobbed. Gina couldn’t get out of the bag, she was stuck until Lucy would let him out. 

About an hour must have gone by when Mrs. Abbot came home. She heard a little crying noise coming from upstairs. 
“Whatever is that?” she said to herself. She climbed the stairs and had a look for herself what was happening. “Oh, you silly girls. What’s happened now?” Lucy looked over her shoulder and quietly said;
“Gina doesn’t like me anymore.”
“Well what makes you say that dearest.”
“I heard him talking with Victoria, he misses real girls.” Mrs. Abbot undid the drawstring on the panty bag. The meek face of Gina appeared from the smelly washing.
“Gina. You do still love Lucy don’t you?”
“Yes, Mrs. Abbot, very much.”
“He said he misses girls’ pussys.”    
“You mean to tell me the two of you haven’t played with your sissy pussys yet? All right, I think I know what needs to be done here. Gina, come with me to my room.” said Mrs. Abbot. He started to put his clothes on. “Don’t bother with your clothes, you won’t need them for this.”

In Mrs. Abbot’s bedroom, she and Gina sat down on the bed for a chat.
“What your missing in your relationship with Lucy that you had with regular girls is sexual intercourse.”
“Yes.” said Gina.
“Now you know sissies have their own pussy, a nice tight hole around the other side.”
“…Anal sex?”
“Of course darling, not sure why Lucy hasn’t tried it with you yet. To busy dressing you up I suppose. But an exciting and fulfilling sissy relationship needs at least a little penetrating action, so I’m going to introduce you now to a whole new world.” Gina was very hesitant and quickly looked for an excuse. 
“Ah, well I’m not sure…”
“PLEASE, Gina. I’d like you to lay over my lap please.”
“Yes Mrs. Abbot.” He did as he was told, his bare bottom was completely exposed. Mrs. Abbot put a rubber glove on her right hand, then smeared her index finger with lubricant. 
“Now this may seem a little strange at first but I’m sure you’ll love it.” she promised. He began to feel even more nervous, he started to shake and his buttocks clenched. “Gina, don’t be nervous.” she said, parting his bottom. “Just relax, relax and enjoy.” With that, she gently inserted her finger into the little hole. He let out a short but loud groan. “Is that good, Gina?”
“It feels funny.” he cried.
“Well lets give it a bit more time shall we?” She moved her finger up and down gently for about a minute until she noticed something. “My my, what’s that? I think your starting to enjoy this, I can feel your dolly waking up. But don’t you dare mess up my tights.”
“Aahh, no, ma…dam.” he said excitedly.”
“How about I push in a little deeper missy? suggested Mrs. Abbot. Her protruding finger pushed in deeper making more squishing sounds. He gasped and moaned loudly. “OK, that’s enough of that, let’s try a dildo shall we?” The next thing he felt was a large, fleshy thing trying to enter him. Mrs. Abbot gently eased it in about half way, then turned it on. The vibrations sent waves of pleasure throughout his body. He’d just discovered a pleasure zone he never knew existed. “All right, that’s enough for now.” He got up off Mrs. Abbot’s lap “Oh dear, we’ll have to do something about that hard on. Here.” she said, taking off one of her shoes. “I want you to milk your little poppet into this.” He’d never been asked to masturbate into one of Mrs. Abbots expensive high-heeled shoes before, so looked at her with uncertainty. “Go on, you won’t get into trouble.” she reassured him. She held it out , he took hold of his dolly and began pumping. It didn’t take very long. In just a few seconds his cum shot out of him and splashed onto the insole of Mrs. Abbott’s shoe. “Wonderful.” she said when he stopped. She held the shoe up to her face and took a look inside. His thick, creamy cum was running down the slope of the insole and into the toe box. “Oh, what a mess you‘ve made, you’ll have to lick it all out of there, but save some for Lucy won’t you.” 

Luckily, Lucy accepted Gina’s explanation, but still wanted payback for him kissing another girl. At this time of year there is a fair in town, and on previous years Lucy had worked in the kissing booth. This year however, Gina was going to be in there. This was Lucy’s revenge. So, at the weekend, Gina’s moment of destiny had finally arrived. There wasn’t a chance of getting out of this, Mrs. Abbot had already agreed it was a good idea. He would of course be dressed as Gina for the kissing booth, and Gina was to be dressed as a cheerleader. He was worried that despite being dressed as a girl someone may recognise him. Mrs. Abbot told him not to worry and gave him help in getting ready. She started by giving him a scented bath to give him a true girly scent. A pair of silky pink rhumba panties were his underwear today. His lacy white bra was padded with small, perky teenage girl sized breasts. Mrs. Abbot gave him a lot of help with his make up, making sure he had it right down to the very last detail and to leave customers at the booth in no doubt they had just smooched a gorgeous young lady. The cheerleader outfit was a sexy red, he wore it with white trainers and a blond pigtail wig.
“Do I look OK Mrs. Abbot?”
“You look absolutely stunning Gina darling.” replied Mrs. Abbot. Her compliment sent a surge of female gratification through his body, so much so he did a little twirl, sending his skirt flying outwards. 
“Oh thank you Mrs. Abbot.”
“Well come on, we can’t stay here all day, let’s get going, and don’t forget your pompoms.”  

Gina’s booth was a small pink tent with a lip shaped sofa inside. Mrs. Abbot was outside taking the money, it was £2 for a minutes worth of snogging a cheerleader. Before they started, Mrs. Abbot gave him a little test to see that his kissing technique was up to scratch. 
“I’ve left a handbag by the sofa with some lipstick inside, make sure you top up if you need to.” 
“OK, Mrs. Abbot.” A line of lusty men had begun to build up outside, with even one or two women. He sat nervously awaiting his first customer. A young man of about 17 in glasses stepped through the curtains. He gasped in delight when he saw the cheerleader, he was shaking, and was more nervous than Gina. 
“Hi, like to sit down?” asked Gina, stroking the place on the sofa where he wanted him to sit. He sat down and duly announced;
“I’ve never kissed anyone before, apart from my mom.”
“Oh.” replied Gina, before taking a deep breath and kissing him hard on the lips, it was so passionate and intense the poor man was out of breath when his time was up. The next customer was a very tall man, it was very awkward when they tried to smooch on the sofa. So Gina suggested they stand up. Gina stood on the couch, which at the same time showed off his sexy legs. The man clearly appreciated it as a bulge formed in his trousers. 

The day continued smoothly, kissing, smooching and even French kissing the punters. This was until it reached a tricky bit. A familiar customer. It was John, his friend from university. Gina hesitated as he sat down next to him. He softly kissed his friend on the lips, it felt very awkward and all the time he imagined Lucy laughing herself silly at his predicament. 
“Boy, your good at this.” said John as he left the tent. “Just as good as your boyfriend in the line said you were.” Boyfriend? Gina asked himself. All was soon revealed by the next customer, a boy about 19 with blond hair tied into a ponytail. He was wearing jeans and a t-shirt, there was something a little effeminate about the way he walked. 
“Hello Gina, everything OK?”
“Lucy, is that you?”
“Well of course it is silly.”
“Why are you wearing…boys’ clothes?” 
“So I could come to see you. I borrowed them from your stash of boys’ clothes, I don‘t have any of my own.” As they embraced and began to kiss, Gina thought how strange it was that now he was the girl and Lucy the boy. He felt quite emasculated and weak, his outfit so much more embarrassing than Lucy’s, but somehow much more comfortable and interesting. In a sense, he found he had become more at ease with female attire. When they’d finished their long and passionate kiss, Lucy put her finger over Gina’s lips.
“Don’t say anything Gina my love, I’ll see you later.” she whispered. At just after 5 the fair drew to a close and Mrs. Abbot drove him home.

Once home Mrs. Abbot turned to Gina.
“Why don’t you go on up to Lucy’s bedroom, Gina? I think she’s waiting for you.” He climbed the stairs and knocked on Lucy’s door. 
“Come in.” said Gina. She was laid on her bed, wearing only her panties, bra and stilettos. “Close the door after you though, Gina. We don’t want Mummy to see what were doing.”
“What are we going to do?” He asked sitting on the bed. 
“Well…why don’t we make love. I’ve always wanted to have sex with a cheerleader.” she giggled. Lucy got up and whispered in his ear; “Tonight I will pop your sissy cherry.” Gina felt a surge of excitement as Lucy quickly helped him out of his cheerleaders’ costume, Lucy took off her bra and panties and kicked off her pumps, their clothes lay scattered across Lucy’s bedroom floor. Lucy went on top of course, as they began a bout of heavy petting and kissing. In the secret world of Lucy’s bedroom, only Lucy’s dolls and teddy bears could see the little sissies’ passionate embrace. Mrs. Abbot downstairs could hear the squeals of pleasure from the two sissies as their soft red lips explored each other’s bodies. Gina’s time to be de-flowered came when Lucy worked herself into a sexual frenzy. “Now, Gina, I want you to get down on your hands and knees.” Gina did as he was told, he lay his face on Lucy’s pillow and raised his quivering buttocks into the air. Lucy lubricated her dolly then began to examine Gina’s ass. She pulled his buttocks apart and gently began to insert herself into him. Gina yelped as the head of the slippery intruder pushed its way into his little hole. It hurt for a little while so Lucy went slow and easy for the first few minutes, but this soon faded. “Better yet?” asked Lucy patiently.
“Oh yes, Lucy. Please fuck me now.” he said excitedly. A request Lucy would not, and could not refuse. She grabbed his buttocks and began to pump in and out of Gina’s hot sissy pussy. Gina loved it, he began to thrust his ass in the air to meet the strokes of Lucy’s penis. “Oh Lucy that’s wonderful.“ cried Gina. While Lucy was intensively pumping away, Gina reached for his own penis. He only had to give it three or four pumps when he cummed all over Lucy’s satin sheets. Lucy was to busy to notice, she was about to build up to her own almighty orgasm. Her sissy little clitty exploded deep inside Gina, producing a strange yet delicious sensation. They collapsed exhausted onto the bed, laying in a pool of Gina’s spunk. Lucy took her little lady out of Gina, a stream of her cum dribbled out of Gina’s ass and onto the already soaking sheets.

Thanks for reading. Send your comments to: shoegirl900@yahoo.co.uk