crossdressingstories
patreon
A Special Surprise
🕑 Added 2022-06-26 16:21:53 +0000 UTCI first met Jake a year ago. He stepped into my shop to spend some money that he had for his 18th birthday. He was a nice lad. Short, effeminate looking with shoulder length hair. At first I was not sure if he was a feminine looking boy or a masculine looking girl.
My shop sold games and comics. Originally I had been a sleeping partner but when my friend decided to sell up I bought him out and had to work in the shop myself. I did employ a couple of people who would help me out from time to time but I often found myself in the shop on my own. At 50 I sometimes felt that I was a bit out of place but I knew my stuff and I soon enjoyed myself.
Jake became a regular in the shop. Often he would just come in to chat. Eventually I offered him a job working in the shop. He gratefully accepted and I found myself really looking forward to going to work. At first, Jake was a bit candid about his private life but then slowly started to open up. He had spent most of his childhood in care homes. When he was 14 he was fostered and stayed with his foster family until he was 18. He now had his own flat and working for me had allowed him to get the things he wanted. Sexually I was unsure. He never spoke about having a girlfriend or a boyfriend. His mannerisms though were very feminine.
On Jake's 19th birthday I asked him if he wanted to go out for a drink. He was happy to be asked but said that he always felt uncomfortable going into bars or pubs. We decided to compromise and when we shut the shop we would have a quick drink in the store room afterwards. I locked the door to the shop and switched the main lights out. We sat in the back room and Jake produced a bottle of Prosecco from the fridge. Drinking from coffee mugs we had one and then another in quick succession. I was hungry and so the wine went to my head a little. I was glad that I only lived a short walk away and not in the house that my now ex-wife of five years lived in about ten miles away.
"Cheers Dad." Jake said as we clicked mugs.
Jake often referred to me as 'Dad'. He had even given me a Father's Day card earlier in the year.
"Cheers son." I said with a chuckle.
Jake looked at me intently and sighed. It was a big sigh and his shouldes slumped.
"I can trust you can't I?"
"Of course you can."
"I want to be your princess."
I stared at Jake and tried to work out what he meant. Nervously he sipped his wine and then sighed again.
"You want to be a girl?"
"Sort of." Jake said with another sigh, "Whether or not I would have the operation or not is another matter."
"Do you dress up in girls clothes?"
Jake looked at me and smiled. I knew what the reply would be before he said it.
"When I'm at home I am Becky."
Since my divorce I had dived headlong into my work and so sex seemed a bit of a distraction. All of my adult life I was positively hetrosexual but here was a new opportunity. Then, I thought that Jake had not mentioned sex, just that he had a female alterego.
"Wow." I said, "I can almost imagine you dressed up."
"Can you?"
"Yeah. I cannot imagine exactly but I can picture you as a girl."
Jake fished in his pocket for his phone. He opened the gallery and found a picture and held it up. Here was Jake, or should I say Becky, was wearing a pretty summer dress. She looked amazing. My cock twitched.
"I have others but I'm not sure if I am ready to share those."
"Oh just one more."
Jake flicked though some more pictures and then held up his phone to show me.
"It's a bit clichéd but I just love this look."
Becky had her hair in bunches. A white shirt with a tie, slightly undone. Short, pleated check skirt which did not quite cover the tops of her black stockings. She looked cute and slutty at the same time. She had a lollipop in one hand and a test paper with an F mark.
"You look a little flustered."
"You look great."
"Thanks." Jake smiled and took another sip of his wine.
I drained my drink and poured another for the pair of us. I could feel my pulse in my cock. This was one heck of a strange sensation.
"I'd like to live full time as a girl but I don't have the courage to do it. I wasn't sure how you would react."
"Do you honestly think that I would care?"
"No, I suppose not but it might have been a bit of a shock. I just didn't know how to approach the subject."
"So who took the picture?" I asked. There was no sign that it was a selfie.
"I did, delay timer." Jake said sadly, "I don't have anyone to take pictures for me."
I took that as a hint and while it was not an open invitation for sex, the idea of taking pictures of Jake as Becky was quite exciting.
"Well, if you ever want to do any more pictures any time I could help"
Jake looked excited. He became very animated and smiled. He had a really nice smile and my cock stirred in my jeans again.
"That would be fantastic." He beamed.
"No problem."
We finished our drinks and started to get ready to lock up the shop and head home. We cleared our mugs away, tidied up and we was about to leave when Jake touched my arm.
"How about now?" He asked, "I'm a bit merry and I think that might be why I have a bit of confidence in this. Besides, you took it so well."
It did not take me long to make up my mind.
"Sure, ok."
"Great, it takes me ten minutes to walk home and at least half an hour to get ready. Let's say be at mine in an hour?"
I had a couple of things I needed to do myself so agreed readily. We locked the shop and went our separate ways.
It was just over an hour and I found myself knocking on Jake's door. Well, maybe in this instance I should say Becky's door?
I could hear movement inside and then the door opened. I was taken aback. A pretty girl stood at the door. Her hair was swept back in a loose ponytail, carefully applied makeup accentuated her feminine features and she wore a pretty white dress and a pair of Converse. She looked amazing.
"Hello Daddy." Becky said with a shy smile.
"Happy birthday Becky."
Becky gave me a hug and planted a kiss on my cheek. I found myself sliding my arms around her waist and hugging her back.
"Whoops, lipstick." Becky giggled as she wiped some from my cheek, " Follow me."
Becky led me into the living room. There was another bottle of Prosecco on the coffee table, opened with two glasses already poured. A camera stood on a tripod facing the sofa. Becky handed me my drink and we clicked glasses.
"Do you know much about cameras?" Becky asked.
I looked at the one on the tripod.
"Yeah, it's just a newer version of the one my ex-wife had."
"You mean Mummy." Becky said.
I smiled and nodded.
"Well it is all set up." She added, "You will really only need to press the shutter."
"Ready when you are." I said putting my glass down and standing ready at the camera.
"I've been ready for almost a year." Becky blushed.
"What do you mean?" I asked pressing the shutter as she posed.
"I've wanted to do this for ages. Pretty much ever since I first met you."
Becky knew how to pose. She went from pretty to sexy and back again. The fact that I had know Becky as Jake for a year seemed immaterial.
"Are you having fun?" Becky asked eventually glancing at the bulge in my jeans.
"It's a very sexy experience." I admitted, my cock twitching in anticipation.
"Shall I put something else on?"
"Sure, I must have taken about a hundred pictures so far."
Becky grinned and then brushed past me to go and get changed. She paused a second and I planted a kiss on her lips. Becky blushed again.
"I won't be long." She said and disappeared.
I poured another couple of drinks and sat on the sofa. I gave my cock a gentle rub through my jeans.
A few minutes later Becky entered the living room. She still had the Converse on. Stocking clad legs led up to a glimpse of thigh. A short, pleated check skirt white shirt with a tie, heavier makeup and bunches.
"You seemed to like this earlier." Becky said flirtatiously.
"I did."
Becky started to pose while I took picture after picture. She started out quite tame but after pausing to finish her drink, she got more and more raunchy. Every now and then I caught glimpse of her white panties with red polka dots. Try as I might I could not see his cock, or should I say her 'boy clit' so I suspected she had either tucked it away or It was very small. My cock was aching painfully in my jeans.
She bent over the arm of the sofa and wiggled her bum in my direction. I took some more pictures and then she arched her back and thrust it further out. The skirt shifted to give me an uninterrupted view of her cute arse covered in white cotton and polka dots.
"You like?" She asked as I took even more photos.
"You have a gorgeous little bum."
"Thanks." She said and with another wiggle, moved her hand round and slipped the panties down a little.
I pressed the shutter a few times and then stopped.
"What's wrong?" She asked and stood up to face me.
"Nothing." I assured her, "This has just been a crazy couple of hours and I don't want to make any presumptions as to how this will end."
Becky stepped up to me and took my hands. She looked into my eyes and smiled. While I had seen Jake smile hundreds of times, as Becky, the smile had an element of wonder in it. Stepping closer she planted a kiss on my lips and then pulled back.
"Does that answer your question?"
I pulled her close and started kissing her again. Our tongues met and it felt like electric shocks. She felt good in my arms and my cock was fit to explode. I would try and talk her into coming to work as Becky. Working with Jake was fun but working with Becky would be amazing.
"Sit on the sofa." She urged me.
I sat. Becky adjusted the camera on the tripod and pressed a few buttons. She then stood in front of me between my legs. I sat forward and put my arms around her waist and nuzzled my face into her stomach. Becky ran her hands through my hair.
We stayed like this for a while and then she crouched down in front of me and began to fiddle with my jeans. Her slender fingers undid my belt and then the button. She took hold of the zip and then slowly started to pull it down. Once undone she slipped a hand inside and under the material of my underpants until she found my throbbing cock. Pulling it out she lowered her head and took it into her mouth. I watched as she sucked my cock and it was my turn to play with her hair. I looked at the camera on the tripod. There was a slowly flashing light on it. She was recording this. I decided that I would try and make it a video worth watching and then ignored the camera totally.
"I want to do the same to you." I said.
"Really?" Becky said as she lifted her head to look at me.
"Very much so."
"How do you want me?"
"Like you was earlier when you bent over the sofa."
Becky got up and assumed the position. I had got up and to save me tripping over my jeans I had pulled them off completely. I had also pulled off my shirt and so I was naked. I crouched behind her and took hold of her panties. Slowly I began to pull them down over her buttocks. I kissed the soft skin and continued to pull her panties off. Parting her legs I examined her boy pussy. I ran a finger over it and then pressed my face between her buttocks and began to lick it. A free hand slipped round to find her boy clit. It was small and hard and twitched when my hand closed around it.
"Lick me Daddy." She begged and her cock twitched again.
I continued to lick and Becky began to moan with pleasure. I definitely wanted Becky to replace Jake in the shop. I stood up and my cock nudged against her buttocks. She reached under a cushion and handed me a bottle of lubricant.
"You had better use this." She said, "I have never had a real cock inside me, only my dildo."
I flicked the lid and squirted some lube on her boy pussy and then some on my cock. I gently pressed the tip of my cock against the puckered entrance and started to push it inside. Slowly and surely my cock got deeper and deeper inside her. Becky gasped a few times and called out but eventually I was fully in. I began to fuck her, slowly at first but as she got used to it I pressed harder.
I fucked her for a few minutes and then pulled out. She gasped and then stood up and turned to face me again.
"That felt fantastic." She said, "I so want you to cum inside me Daddy."
I sat on the sofa and she straddled me. Becky took hold of my cock and guided my cock back inside and started to ride my cock as we kissed. I could feel her hard boy clit rubbing up against my stomach. I hoped that she would cum on me.
As we fucked we kissed. Becky gasped and moaned as my cock disappeared inside her. I was close to ejaculating when she got up.
"I want to turn round." She said, "I love how my little clitty bounces and I want to see it in the video with a real cock in me."
We adjusted our position and she guided me back in. She bounced up and down on my cock and giggled. I gripped her waist and helped to steady each thrust.
"Cum in me I beg you." She said sensing me tense up.
I pulled her down hard onto my cock and then it started to pump my load into her. Becky squeeled and then gasped as she came too. We lay back panting and I held her in my arms.
"Can we go to bed?" She asked after her breathing returned to normal.
"Sure."
She got off me and looked at me.
"Maybe a quick shower first?"
She grabbed me a towel and showed me to the bathroom. I quickly showered using Jake's shower gel. I noticed that there was also a more feminine option that I hoped Becky would use.
Once I had done I wrapped the towel around me and walked out. Becky was waiting for me holding her towel.
"Five minutes." She said, "Bedroom is there."
I followed where she was pointing and dropping my towel got into bed. I lay back and waited. Her camera was now fitted up to to TV and I could see myself sitting on the sofa. Minutes later Becky walked in wrapped in a towel. She dropped it and after clicking the camera into play mode climbed into bed next to me.
"I thought we could watch ourselves."
Cuddled up in bed we watched us having sex from earlier. My cock twitched and began to swell. I reached down and felt her boy clit which was having the same reaction. When the video finished I wriggled in bed.
"I just want to try something." I said and slipping down in bed took it into my mouth and began sucking it.
Becky moaned and lay back. It was not long before it twitched and began to squirt cum into my mouth. I swallowed it and moved up to kiss her.
"My turn." She said.
Becky began to suck my cock and I too filled her mouth with cum. She too moved up and kissed me and then we cuddled up and fell asleep.
***
"Wake up Daddy." Becky said shaking me.
"What time is it?"
"Just gone midnight. We have to open up in the morning and I have some things to think about."
I got out of bed and wandered around her flat to find my clothes. Once dressed I kissed her and left.
"See you at the shop." She called after me as I went.
***
The following morning I was unlocking the shop when an attractive young girl approached me smiling.
"Hi Dad." She said, "Do I look ok?"
Becky was wearing a Suicide Squad t-shirt, a short black skirt with lace trim and three quarter length black leggings. She had small, pert little tits for extra measure.
"You look wonderful."
"I made the decision last night after you left. Jake has left, Becky now works for you."
"Fine by me."
We went inside and started to get ready for the first customers of the day. As Becky bustled around the shop it felt as if she had always been there.
By the time it came to closing time we had had enough. It had been busy day and we were both tired. I went into the back room and Becky handed me a mug. I peered in to see if it was more Prosecco but it was a coffee.
"Can I ask you a question?" Becky asked.
"Sure."
"I want to be your daughter."
"My special daughter?"
"Yes, can I?"
I put my cup down and held her. She felt good in my arms and I wondered if she was my daughter, would I get to fuck her again.
"Yes."
"I could change my surname and I might ask to have the medication so that I turn more into a girl."
"That's a big step."
"But one I want to take if you will have me."
I hugged her and we kissed.
"I'm here for you." I said eventually.
"Thank you. I love you Daddy."
"I love you too."
"Can I come home with you tonight? I want you to make love to me."
My cock twitched again in anticipation. She felt it against her and giggled a real girly giggle.
"I will take that as a yes then."
