Loser To Lauren

This story contains content including strap on play, cross dressing, and general anal play. If this content is not what you are looking for then you can click away now, I promise not to get offended.

This story aims to get away from the dominant woman forcing the guy to do it and then he secretly wants it anyway sort of story and looks to get into the more mutual side of things and how wonderful it can be if you find someone who is willing to give themselves over to you entirely.

All work is fictional and as such is not taken from anyone else, If there are similarities to other writers then I sincerely apologize but chalk it up to great minds thinking alike.

I just want to thank Trixter for all their help with editing. You have been a great help and I could not have gotten this story finished without you.

This is my first story so go easy on me ok guys!

*****

Hi, my name is Chris and I am an 18 year old guy. I was not popular at school as I was predominantly interested in playing computer games and reading comic books. This inherently caused my other interest, girls, to completely ignore the fact that I existed.

When I moved into Sixth Form College I took my interest in PC hardware a step further and became a freelance IT support guy around or town in order to pocket some extra cash. This basically meant that I would get a call from my mum to tell me that one of her friends was having issues and they needed someone "Techy" to come and figure it out for them. A lot of the time this involved me going to their place of residence and applying the old turn it off and on again trick to fix their issues. Every time she would call to tell me that someone was having issues I would always hope beyond hope that it would be Mrs Clark that needed help and that I could go to her large home at the edge of our town. This was an unlikely event as they had a lot of money and they would more often than not just buy new stuff but on one fateful blustery October day, I finally got that wish.

"Chris, I have one of those IT thingys that needs doing again" my mum called up the stairs at 9am. I had the day off from sixth form and was hoping to lie in, drink some cold Lemonade and play my PC til my fingers hurt.

"If this is Mr Anderson calling again to find out if his home telephone can connect to his Wi-Fi then I might just throw the damn thing at him" I yelled down to her. She could sense the irritation in my voice at being woken up but she couldn't stifle the giggle at knowing that Mr Anderson wouldn't know his arse from his elbow if his wife didn't remind him.

"Actually..." she cooed in that voice that mums do when they want you to do something and they know there is no way that you won't bail out of doing it, "It's Mrs Clark, you know Amy's mother?" she continued and I could hear in her voice that she was openly grinning now.

"Are you serious?, surely she could have a million guys come over and do that, she probably even owns her own IT guy" I shouted down the stairs in a reflex, not really meaning it and processing that I might be in Amy's house at the same time as her.

"She tells me that they sent the guy away because he was talking down to them and making them feel stupid, she asked for you by name and everything. I told her you could be there at 11:00, hope that fits around your schedule."

I sat there for a minute completely dumfounded, a million scenarios going around in my head. Maybe my mum put her up to this, maybe Amy did and they were planning to embarrass me somehow. Finally I settled on the fact that she would pay good money and it would be worth the embarrassment, after all it couldn't be worse than most of my days.

I jumped up and went for a shower, I had barely any hair on my body and I shaved what little I did have on a fairly regular basis as I liked the feel of the cool air on my body and the way my clothes felt as I pulled them over my smooth skin. I showered and shaved the little stubble on my face and brushed my long hair tying it up in a ponytail as I did most days. I brushed my teeth and dressed in a plain white T-shirt and Combat Trousers before I sauntered downstairs to grab some things I thought I might need (screwdrivers, portable hard drive reader etc) and headed out the door. As I closed it my mum called after me "Say hi to Amy for me" in a sickly sweet voice.

I headed out to my car, mum and dad had bought me an old style fiesta for a first car and it was doing well for an old thing. I drove up to the Clark's house and pulled into their driveway. The area for parking cars was bigger than most of the rooms in our house combined and parking my little dinky fiesta so close to their shiny new Audi and Jaguar seemed like a crime.

As I walked up the large front door and rang the doorbell I felt a flutter in my stomach. I don't know if I was overwhelmed by the size of the house but I certainly felt uneasy. I pulled myself together reminding myself that if I could solve the issues they were having then just maybe I would get a nod or a hello from Amy at college and feel like a normal kid for once.

No such luck, their PC was outdated which surprised me and they only wanted to recover some data before they replaced it. "We just wanted to get our pictures of our beloved pets off of their before we buy a newer model." Mrs Clark had told me. "I understand, we lost our dog too and pictures are all we have left of him." I got a bit choked up as Buster had been my best pal and always cheered me up when I had a bad day at school. The hard drive reader was pulling the data off and to my surprise Mrs Clark pulled me into an embrace as she saw I was fighting back tears about my old buddy.

"They are more like family than we realise aren't they?" she soothed as she stroked the top of my head. The reader finally finished pulling the data and using my laptop I put all of her data onto an external hard drive. "If you keep hold of this til you get your new PC then I will pop by and put all of the new data on it for you." I said as I held out the hard drive. "You are very sweet." Mrs Clark beamed a smile at me; she was a beautiful woman, in her 40's but still a knockout.

"If you could not tell Amy about the whole me being a wuss and you having to hug me, I'd appreciate that."

She laughed heartily but then with a semi-serious scowl said "Don't be afraid to show emotion Chris, there are too many enhancements in technology and we don't need emotionless 18 year old robots roaming around." She chuckled. "On that note actually, why is it that my daughter does not hang around with guys like you? all the guys she brings home are rude."

"People like me don't get to be in the same circles as girls like your daughter Mrs Clark." I said rather sheepishly.

"Are you saying that my daughter is mean to you at college Chris?" she seemed hurt.

"Not at all Mrs Clark", I reassured her, "but Amy is popular and I am...a geek."

She looked at me quizzically and then it seemed to click "well I will have none of that nonsense around my house, go out back and see if she is sitting in the garden, say hi and hang around for a bit. I'm pretty sure she has Kat over."

It would be an absolute shock if she didn't; they had been attached at the hip for almost their entire lives. Where one went the other went and they were inseparable during any break and lunch time. They were super close too, which means what one of them knew the other knew which was bad for me. I had asked Kat out once, back when I had any sort of confidence, and she had turned me down. She was polite enough but she informed me that I was "Not her type". I had seen the two of them pointing at me and giggling for a following number of months and a small glimmer of hope had me believe that Kat was trying to get Amy to notice me. These hopes were dashed when one of the popular guys informed me that they had spread rumours about me having a small dick. I didn't hate them for it but I was disappointed that they were like all the other girls I knew (I later found out this rumour was a lie made up by the boy because Amy had rejected him).

I approached the back door and neither of them was out there so I turned to leave, Mrs Clark had other ideas and ushered me towards the stairs.

"I'm sending Chris up to you girls to say hi she shouted" and pushed me up the stairs, there was no answer but the music was very loud coming from their room.

I knocked on the door but no one answered, I could hear muffled voices but the music was drowning everything out. I knocked a second time "Amy, its Chris, Your mum said to come up and say hi". They didn't answer so I pushed the door, it wasn't completely closed and it slowly swung open and I could see Kat sat on the edge of the bed with her hair in bun and Amy giggling as she applied make up to her face.

Kat looked around Amy at me and Amy, who had straddled Kat at the waist, craned her neck to look at me.

"Chris Right?" Amy started "Did I forget homework or something?" she asked. I felt a twang of pain as if the only reason I would ever be at a girl's room would be to bring homework.

"No I was just fixing the PC and your mum insisted I come up and say hi, I was going to leave you in peace but she wouldn't let me leave."

"That's mum." Amy said with a giggle

"I'll see you around then." I said hurriedly as I turned to leave.

"Wait!" yelled Amy as she leapt off of Kat's lap and grabbed my arm "As you are here you can hang with us if you like, we were going to have a girly day and then hit a party later, are you going?" she asked me with a hint of excitement in her voice.

"I didn't know there was a party and I probably would not have gotten an invite anyway." I said dejected. I was sad but I was at least a realist.

"You can still hang with us if you like?" Kat encouraged. I wasn't sure if it was out of pity or if it was genuine but I took the offer.

"If you guys don't mind then I would love to hang around." I smiled, I couldn't help it, pity or not this was awesome. I took a seat on an armchair in the corner of the room.

"Hey if you don't mind us messing around and doing all our girly bits, you never know we might even give you a makeover." She winked as she turned to her doll to carry on.

Now before we get on to the next part, I think I should give you a bit of a back story.

I had always liked girly things. I was jealous that girls all had so many things to choose from. So many pretty things, with accessories and make up. I had always wondered what it would be like to get all dressed up in some sexy heels, with my make up on and hanging out with the girls. It was something that I masturbated too often and was a fantasy that I would not dare to bring to reality. Now with that said and all these feelings floating around my head, I have no idea why my inside, wishful stupid voice was actually saying aloud.

"Yes please."

Total deathly silence, followed by a slow head turn of both girls looking at me with shocked faces, and it dawned on me that I had said it out loud. "Pass it off as a joke, leave, do something!" I willed myself. Kat beat me to the punch but I was at least thankful of her to break the silence.

"Wait, Chris, are you gay?"

Amy turned and scowled at her so hard "Kat!" She yelled, "Don't be so insensitive, If he wants to do that sort of thing then it's his business. Doesn't mean he is gay."

"Sorry." Kat mumbled, but you could see she was genuinely concerned.

"I'm not gay." I plucked up the courage to say, although very quietly.

"Tell me about it" Amy's tone had changed; she led me by the arm to the bed in between them. "You can trust us, right Kat?."

"Of course" Kat was a few things, but a liar she was not, she took that very seriously.

"I'm not sure.", I began, "It's just something I was always interested in, something I looked for online if you know what I mean, and I just get bored with guy clothes you know? It's all T-shirts, jeans, combat trousers, whereas girls get to wear all these pretty things, and heels..." I trailed off as I notice a stirring in my trousers; I was not the only one.

Kat nodded to it, Amy followed her glance and turned back to face her. They nodded to each other and looked back to me.

"I understand that it was difficult for you to tell us that, and we are very happy you could confide in us." she smiled and touched my arm "and so that you can feel safe that we will keep it to ourselves, we wanted to share a secret with you." she turned to Kat to continue.

"Everyone knows we are good friends." Kat began "and we have always been close. As we got to 17 and a lot of people in School were having sex, we felt pressured into joining the culture but neither of us was ready." I felt a pang of guilt, that I saw these girls as all the rest but not stopped to think that they might have peer pressure to deal with too.

"So we came up with an agreement." Amy continued "Where we would both be ready when the time came." they sat next to each other and locked hands.

"Do you know what a strap on is?" Kat asked.

I nodded. My trousers did too.

"We prepared each other for sex." Amy stated matter of factly.

"We aren't Lesbians" Kat answered my mental question that I dare not ask. "We trusted one another and why do it with a stranger when we could help each other out?."

I suddenly understood these girls better than I ever thought I could.

"Truth be told no sex has been better since." Kat said, for the first time it would seem because tears formed in Amy's eyes.

"Same for me" she said and Kat beamed a smile at her. "But we promised never to do it again; we don't want to threaten our friendship by going down that road."

"So...where do we go from here?" said Kat to the room in general.

Amy looked at me, then down to the brush in her hand, to Kat and finally back to me and smiled a broad smile.

"Her first" she motioned toward me and Kat agreed with excitement.

"First things first, kiss me" Amy said out of the blue

"Kiss...You...On the lips?" I couldn't stop my voice from shaking as I said it.

"Whenever you are ready." Amy just stood there, inches from my face.

I took a deep breath, I'd imagined this moment a million times as I shot my load into a tissue, but here it was right in front of me and I was determined to make it worthwhile.

I caressed her cheek with the outside of my hand and rested my other hand on her neck gently. I pulled her face to mine and kissed her softly for a slightly longer than normal time and gently let go of her neck and pulled away. She had her eyes closed and suddenly shook herself out of a stupor.

"Wow" she said. "For a first kiss that was pretty damn impressive."

Kat had a stunned look on her face "I said no, to that, because you weren't 'my type'" she stared at the ceiling, "I'm an idiot". That made me smile.

Amy had recovered at this point and looked into my eyes, she assumed the position on my lap that she had occupied when I first entered the room on Kat's lap, but this time I was the lucky one.

"We can do the full works, make up, clothes, shoes or anything you want." she put her fingers to my lips to stop me talking "But it has to be what you want and I don't want you to say no just because you think we will be weird about it, if you want it then we will make it happen for you."

"I don't think I have wanted anything more." I said with complete conviction.

The girls squealed, whispered something to one another and nodded enthusiastically. I would later find out that this was them discussing how I might one day become the third person into their inner circle, that I was a loner and that I would provide the one thing neither of them had in this relationship. That thing was male company and more specifically male parts.

Amy began by plucking at my eyebrows whilst Kat took her talent to my fingers and began manicuring, shaping and painting my nails a deep purple colour. I know that having your eyebrows plucked hurts but so lost in the moment was I, that I didn't feel one ounce of pain.

Amy maintained eye contact throughout the whole process, only was our gaze broken when she asked me to close my eyes to apply the eye shadow to give me the smokey look.

They worked for a good 2 hours before I was told to walk to the wardrobe. Kat kept some of her clothes here and we were roughly the same height. I wasn't tall but she was tall for a girl and we were both slightly higher than Amy. She compensated by wearing larger heels but I was thankful to be Kat's size looking at Amy's shoes.

They had me step into panties and a suspender belt before pulling me to sit down in the armchair.

I was instructed to point my toes out towards Kat as she rolled a pair of hold up stockings up each leg. I stood up and she attached them to the garter belt. Amy lifted something over my head and positioned it at my chest. She placed some rolled up stockings in the cups and pulled it tight to my chest before doing it up at the back. It was a black Corset and the stockings were to give me some sort of 'bust'. They felt electric against my nipples and I knew my figure must look very feminine. I stood like this looking down at what seemed to be this beautiful woman's long legs encased in silk as my hair was taken out of my ponytail and curled for what seemed like forever until it framed my face.

Whilst Amy was doing my hair, Kat had slipped into an identical outfit to mine. She looked incredible.

They both moved in front of me and smiled as they looked at their handiwork. "Now Heels!" Kat shouted excitedly as she went straight back to the closet and picked out a pair of 4 inch black patent high heels. Amy helped steady me as I stepped into them. Kat stepped into an identical pair.

"Walk around and get comfortable." encouraged Kat

"Wait" screamed Amy as she threw a cloth over the mirror. "I want her to get the full effect."

I smiled and began to walk around the room, I wobbled at first and they had to balance me. Then as I got more comfortable they were whispering to each other again.

Whilst I walked around, Amy had dressed into the same outfit as us, but in white and with white heels to match.

"Big reveal time!" now Amy's turn to be excited. They positioned me in front of the mirror and prepared to pull off the sheet.

"If you don't like it I promise we can help you take it all off and we will just pretend this never happened" she said looking deeply into my eyes.

"Thank you" I said to them both and held my breath, what little I had left from the tight corset, and waited.

When she removed the sheet, for a few moments, I felt like I was looking at someone completely different. I just stared for a while, then I started to run my fingers over the corset and the beautiful girl started to do the same. I touched my legs and the jolt up my spine was incredible.

I felt a twinge and looked embarrassingly at the girls. My dead giveaway was there jutting out above the panties and Amy's eyes met with mine once more.

"How do you feel?" She asked genuinely. She and Kat hung with baited breath for my answer.

"I feel incredible, I love you guys so much" I was overcome with emotion. They both hugged me tightly until Kat began to giggle.

"What's so funny?" Amy asked.

"We have to do something about THAT." she said pointing at my rock solid cock.

"Would you like us to?" Amy asked, slight hope creeping into her voice.

I pondered this question for a moment. Until today these two girls had barely spoken a word to me and now they were offering to do 'something' about my hard cock.

I nodded with trepidation. First kiss, first time fully dressed, first time anyone else was going to touch my dick.

"Do you trust us?" Kat asked.

"Unequivocally." I replied instantly.