Jamie's Journey Ch. 01

This story includes straight, gay and lesbian relationships, cross dressing ... and where this leads to ...

"I really wanted a girl, but it didn't happen. He's a good little boy, but it's not the same." Jamie was playing on the floor. At just five years old he realised he'd disappointed his mother ... because he wasn't a girl.

His father had moved on; resentfully she bought him up. Sometimes when she was angry he wished he could please her by being the girl she wanted. She didn't understand. A dominant, controlling mother, she constantly belittled him.

This had consequences ...

XXXXX

Jamie was so happy when he was found a job working in a bar in London's West End. He had lived all his life in a small village just outside Edinburgh. School wasn't successful for him. With very little encouragement from home he became bored with the routine and discipline of school and was very happy to leave having just reached sixteen.

He hadn't been popular at school. He was very unconfident with few friends. Slight and vulnerable, being bullied was a regular part of his life.

He was so relieved to leave the school gates behind. He knew that he needed to earn money and that meant finding work. With no qualifications he realised that probably the best opportunity would be to work in a local factory on a production line or possibly in a shop or bar. Over the next two years he had months of unemployment, followed by low paid jobs. Eventually he found work in a hotel bar in Edinburgh, and although it didn't pay well, he started to enjoy it.

As a result of his miserable school days he found it really hard to make friends. He was too unconfident to ask a girl out; he was afraid of the misery of rejection. In consequence he spent hours in his bedroom on his iPad, mostly on the porn sites.

He watched endless videos of young girls having sex with well endowed young guys. The girls were amazing. He envied their near perfect bodies, beautiful hair and flawless skin. Sometimes he fantasied being a girl, wearing make-up and sexy outfits.

Just after his eighteenth birthday he decided to move to London and make a fresh start. He successfully applied on line for a job working in a bar in London's Soho. After a long coach trip from Edinburgh, he arrived in London and found a cheap bed and breakfast.

Life in London was so different to Edinburgh. This was a new start. He was free to do anything he wanted. All he had to do was keep working and earn money.

The bar was located in Soho's gay area. At first this worried him, but the other bar staff were friendly and he started to enjoy the work and his new life. After his first pay day he found a cheap room to rent and relaxed, happier than he had ever been.

This was so different. At the bar he was working with and serving people of all sorts of sexual preferences - gay, lesbian, cross dressers and trans. This was really interesting and exciting.

People were what they wanted to be. There were no boundaries, no limits. Freedom.

One of the regulars was an attractive and very sexy teen girl. She came in after she had finished work most evenings. As he served her they started talking - just a few words at first, but over the weeks words grew into conversations. Jamie was attracted to Joanne and nervously plucked up the courage to ask her out. She seemed very happy that he had asked her. They both loved curries so decided on a meal at a nearby Indian restaurant.

Jamie was nervous but so excited. He was going to be with this beautiful girl for a whole evening. Being very inexperienced, he had never before taken a girl out for a meal. They agreed to first meet at a cocktail bar that Joanne had suggested.

She was wearing a tight fitting blue mini dress, light grey tights, and 4" heels. Carefully made up and with shoulder length brown hair, Joanne looked amazing. Jamie felt a stirring between his legs. They were in a world of their own as they talked and drank their cocktails.

Joanne sensed Jamie's inexperience, moved closer to him and gently squeezed his hand. Jamie loved the feeling of her being so close and the excitement of the physical contact was producing a hugely embarrassing reaction. Slowly his cock stiffened and it soon became obvious. He tried to hide it but to no avail. Joanne had noticed.

She giggled, "Its ok, I'm glad you like me!".

"Sorry, can't help it".

"Its fine...". She removed her hand and kissed him on the cheek.

Once in the restaurant Jamie knew the table would hide his embarrassment. The only table left was next to a wall, so they sat at the table side by side, their young bodies close together. They ordered curry and red wine. Both were completely relaxed talking, eating and enjoying each other's company. Joanne gently rested her hand on Jamie's thigh sending a surge of excitement through his inexperienced body. Jamie moved his hand to below her dress onto her knee. His heart was beating fast and his erection was becoming uncomfortably obvious.

"It's ok, I'm here". She gently squeezed his leg ...

"Mmmm!" Jamie was in paradise!

After the meal, hand in hand, just to be alone, they walked back to Jamie's place. They both felt the excitement and were just so happy to be together. Once inside Joanne took off her coat and but her arms round Jamie, holding him tightly into her young body. She felt the shape of his erect cock against her. Jamie put his arms gently around her. She felt so good.

They kissed. It was a first time for Jamie. As she parted her soft lips her tongue entered Jamie's mouth. Their tongues met. Jamie was beyond paradise!

The very experienced Joanne guided Jamie, completely took over his willing body until he entered her. They made long and passionate love. So excited was Jamie that he came three times in just over an hour. Joanne was happily exhausted; she had never experienced such intensive lovemaking and climaxed so many times.

She hadn't smoked in front of Jamie but she needed a cigarette now. She took a pack and her lighter out of her bag,

"Is it ok if I smoke?"

"It's ok"

She took the cigarette out of the pack, put it between her soft lips, lit it and sucked in the addictive smoke and relaxed.

"That's better!"

The sight of her wrapping her moist lips around the cigarette, sucking and inhaling the smoke started to have an effect on Jamie. He felt his cock stiffening again; Joanne noticed and knew what to do.

"Lie down ..." He lay there, seven inches of cock erect.

Holding the cigarette between her lips she straddled him gently taking his hardened cock guiding it between her legs. As she lowered her body, Jamie's hard cock entered her tight moist pussy. The teen kept the smoldering cigarette between her lips. Up down, up down, she was in control, faster, faster ... Jamie's helplessly overstimulated body once again entered his private paradise.

They both finished together with enormous climaxes.

The unconfident Jamie just couldn't believe this was really happening to him. Joanne, snuggled into his firm young body, happy and satisfied after so many orgasms.

"Nobody's ever made love to me like that... ever!"

Jamie noticed her short tight blue dress, black lacey bra, panties and stockings in a pile on the floor beside the bed.

He started to get hard again ...

Joanne's parents would be worried if she missed the last train home so Jamie took her to the underground station and after a long and very deep kiss she ran to catch the last train.

An hour later a text message, "Home ok. Love you lots xxxxxx Jo xxxxxx "

Over the next few weeks they became very close. Sometimes if they were going out to a club Joanne would stay overnight. She often left spare clothes at Jamie's "just in case".

Xxxxx

Beth and Joanne had been friends for most of their lives. They went to the same schools, were in the same group of friends and even liked the same music. Both girls had just turned eighteen and to celebrate they booked a week's holiday in Ibiza, to enjoy the bars, discos, nightlife ... and the sun.

Jamie took it well when she told him. She had booked the holiday before they met. The approaching date only intensified their lovemaking and Joanne was almost living with Jamie by the time she and Beth left for Ibiza.

Back in the flat Jamie felt lost. It was as if Joanne was still there. Her clothes, the smell of her cigarettes. But she wasn't there. He didn't feel good. Just a few hours into the week and he was missing her. There was a whole evening ahead, so he decided to go to their favourite pub and have a few drinks. A few drinks turned into a lot of drinks and some hours later a very drunk Jamie staggered back to his flat.

He collapsed on to the bed and fell asleep.

xxxxx

It was still night when he woke up. He was miserable and worried. Joanne wasn't there. What was she doing now? Was she out drinking, clubbing, meeting other guys? Would she .... his eyes started to water. Insecure, tormented by his imagination, tears started running down his cheeks.

He noticed draped over a chair, the short tight black dress Joanne had been wearing on the night before she left on holiday. Screwed up on the floor were her dark stockings, lacey black bra and matching panties.

He wondered what it would feel like to ...

Hands shaking, he held the dress against his body. It felt nice ... different. He liked it.

Xxxxx

Things had gone well for Joanne and Beth until they reached their accommodation. The twin room they had ordered had just one undersize double bed.

"Sorry ladies, this is all we have left. The room you were staying was destroyed by a group of English girls having a last night of holiday party."

A small room, but at least it was clean. Joanne was uneasy - sleeping would be difficult. She was surprised that for Beth it wasn't a problem.

"We'll be ok as long as we're off our heads ..."

Jo wasn't happy. What seemed a great idea four months ago wasn't now. She just wanted Jamie, his hard warm cock inside her, endless sex, filling her needy young body with his warm love fluids.

While Jo had been engrossed with Jamie, Beth had finished with her long term boyfriend. Out of curiosity she accepted an invitation from a friend from work to have a drink in a gay bar. This was a revelation. She loved it ...

That night they began intense relationship. It lasted a week. Beth had discovered a different world, and she liked it.

But could she tell Jo? Her friend had the most beautiful, incredibly sexy body ... this was going to be difficult. How she would like to make love to her childhood friend, feel her firm breasts, suck her erect nipples, move her hand up inside her dress, stroking her warm thighs ... then ... omg ... feeling her moist juices

The girls were so close that each almost knew what the other was thinking. But if Jo guessed how Beth felt about her it would wreck the holiday and destroy their friendship.

Jo had told her how close she and Jamie were and how she would miss a week of his non stop lovemaking.

Beth knew she had to be careful.

Xxxxx

Unable to resist, Jamie picked up her silky black panties. A smell of sex ... she had been wearing them as they made love. As he sniffed her panties a visible surge of excitement filled his body.

The feel of the silky fabric, the beautiful black lace, how good it must feel to wear them. Women were so lucky. What would it feel like to ...

Uncontrollably turned on, he was soon pulling them up his legs, manoeuvring them around his rigid projecting cock.

A rush of excitement filled his inexperienced body ... he was wearing her beautiful silky panties. He looked down. They were hugging his body, an indescribable feeling...

Jo's bra was lying on the floor. Temptation ... but who would find out? Would her lacey black bra fit him? He adjusted the row of little hooks to the largest fit, he stepped into the bra, pulled it up his body covering his now erect nipples, straps over his shoulders. ... omg this felt sooo good

Uncontrollably excited, hands shaking, one by one he drew the smooth dark 15 denier stockings up his legs.

Would he be able to fit into the little black dress? As he pulled it over his head he realised the material was stretchy. As he pulled the dress down over his panties rubbing against his protruding cock, he could see it was a near perfect fit. He was taller than Jo, so it ended slightly higher up his legs. They had been transformed into gorgeous female thighs, exiting provocatively from under his dress.

If Paradise existed, this was it. He was in a different world ... a different person. No longer Jamie, now a sexy teen girl, a release, an escape. She needed a name ... Vicki ... yes, she would be called Vicki. A new name, a new world.

As he sat down could see that his dress had moved up exposing more of his stocking clad thighs. Pre-cum was leaking from his hard erect cock.

The bulge of the Jo's padded bra shaped the top of the body hugging dress. Inside were his breasts, his sensitive, excited nipples rubbing against the fabric. Putting his hand down the front of the dress, inside the bra he stroked, squeezed, then rolled the nipple between his fingers.

"My god, I'm a girl, a beautiful girl." The words came out involuntarily. He collapsed onto the bed, remembering Jo's favorite position, lay on his back, hips raised, legs wide apart.

Vicki was waiting for her man to make love to her ...

"Come inside me ..."

But there was no one there. Closing his eyes he gripped his cock, masturbated hard while imagining being entered by a sexy, demanding lover.

A deluge of cum ran off his stockings onto the bed. He lay there exhausted and happy.

Yes, now he really was a beautiful girl, Vicki, attractive, needy ...

On the table were Jo's cigarettes and lighter. They made her look so grown up and sexy. Perhaps ...

He got off the bed, took the pack off the table, opened it and put a cigarette between his lips. Yes, just like Jo, Vicki loved to smoke after sex. Sucking nervously as he lit the end, he coughed as the smoke entered his mouth. He tried again, less smoke, success. Again, again - he was starting to enjoy his first cigarette. Vicki was a sexy, confident teen.

Making a coffee he realised how much he loved his new persona, the unfamiliar feeling of the stockings and bra and the gorgeous tight fitting dress.

He lit another cigarette. How well it went with the coffee. Relaxed, one leg over the other, he was suddenly turned on by the expanse of stocking clad thigh. And just like Jo, as he inhaled the smoke, gently at first, his head started spinning. This felt so good.

Again, a mound appeared in the dress. His excited cock was uncontrollably erect. Hand up his dress, he knew what he had to do ... another explosive orgasm followed.

Vicki was born.

Xxxxx

It was 2am. Jo and Beth were tired. Their first night out, they were ready for bed after a day travelling.

The undersized double bed was just too small. Jo decided to ask for a transfer as soon as another room became available. The only person she had ever shared a bed with was Jamie.

Within minutes both girls were fast asleep ... until they were woken by drunken male voices, banging on the door and someone trying to open it.

"Shhh, pretend we're still out." Jo was calm, Beth was shaking.

"What if they get in, break the door down?"

The banging stopped. Silence.

"We're ok now." Jo turned over, away from Beth.

"I'm scared. Can I have a cuddle, pleeese ..."

"Yes..." All Jo wanted was to sleep. She felt her friend's breasts against her back as Beth spooned into her.

And that's how they slept. Friends, their young bodies together.

Beth woke first. She loved the feeling of Jo's soft curvy butt against her carefully shaved mound, her nipples against Jo's warm back. She felt an embarrassing stickiness between her legs. How did that happen? What was her body doing to her? What if Jo noticed?

But she didn't want to move. It felt too good. Her hand was just below Jo's breast. If she pretended to still be asleep and moved it up a little ...

Xxxxx

Jamie was tired. Carefully undressing, putting the little black dress on a hanger, he looked in Jo's pile of clothes and found her favourite black silky Victoria's Secret nightie. It fitted perfectly. He felt so good.

Vicki was ready for her first lover. She felt so sexy ... all she needed was a large cock, moving up inside her nightie, exploring between her legs, entering her needy body, making long, satisfying love.

Woken up by his phone alarm, he could feel the smooth silky fabric of the nightie on his body, rubbing against his erect nipples. Then he remembered the pleasure, excitement, the escape as Jamie the bar tender became the the beautiful sexy Vicki.

Time to get dressed. Driven by his new needs, he laid the dress, stockings and bra on the bed.

This was just the start. He knew he wouldn't fit into Jo's shoes but had she left any makeup? He looked in Jo's small overnight case ... and there was a little pink makeup bag. Mascara, lipstick, eyelashes - it was all ready for Vicki to use

He let the nightie drop down rubbing against his throbbing erect cock. Carefully, so as not to ladder them, he pulled the smooth fifteen denier light grey stocking up his legs. Then the bra and panties.

A surge of happiness and excitement filled him as the short tight black dress fitted into the shape of his body. The feeling was amazing.

After ten minutes of trial and error, carefully applying the dark red lipstick, he was finally satisfied with the result. Mascara was a challenge, but after several failed efforts he learnt the technique. The long false eyelashes almost completed the transformation.

As Vicki he was happier than at any time in his life. Relaxed, fulfilled, this was where he belonged. His new world.

But he was worried. What would Jo say if she found out? What about his workmates at the bar? How would he explain it to people?

He made a coffee, sat at the table. Vicki liked a cigarette with her coffee. He put it between his lips, fumbled with the lighter, then filled his mouth with the addictive smoke. Excitement was building in his body ... this was soo good...

He ran the fingers of his left hand slowly up the smooth stockings, stroking the sensitive inside of his thigh, until he felt the pre-cum on the moist tip of his excited cock. He put his right hand down the front of the black dress until he felt the top of the lacy bra. Threading two fingers between the bra and his smooth skin he found an erect nipple, putting one finger each side, squeezed it firmly.

His left hand was now firmly around his cock, his right on his nipple. As he masturbated his cock faster and faster his fingers tightened like a vice around his hardened nipple. He was so happy. He loved the feel of the stockings, the silky black panties, the sexy tight dress, the taste of the lipstick, the feel of his long eyelashes.

An uncontrollable climax was building inside him like a giant wave in an ocean of pleasure. He came so hard that his whole body shook as he cried out in indescribable pleasure as he shot his cum all over the stockings and panties.

Xxxxx.

Jo started to stir. Beth hadn't moved and was still snuggled tightly into her.

Beth's hand on the underside of her breast felt almost too nice. Her breasts were always incredibly sensitive and she was enjoying the feeling.

Sometimes she had wondered what would happen to their friendship if they both met guys, got married, had kids. Inevitably their friendship would change. She started to feel ... insecure. For years they had confided and in some ways were dependent on each other.

Pretending to be asleep, Beth stirred and "accidentally" moved her hand further up Jo's breast. Her friend gasped. Realising she had gone too far she quickly moved it back ... but then felt Jo's hand on hers, moving it back. Upset by her thoughts, Jo wanted Beth close. Would this be their last holiday?