Cindy's Awakening Pt. 01

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Cindy's girly night in takes an interesting turn...
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Part 1 of the 3 part series

Updated 06/15/2023
Created 04/27/2023
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CINDY'S AWAKENING - PART 1

A girly night in

"Wow! Look at you Cindy! This has got to be your best look yet!"

My bestie Jessica had led me by my hand to her full length mirror, and looking back at us were two glamorous and gorgeous young women.

We had known each other since junior school. Jessica was a shy but pretty girl who lived for her dancing and drama classes. I was the small and unathletic boy who preferred to play with the girls at recess, and was relentlessly teased by both my male and female class mates. I was supposed to be called 'Robert', but even the teachers had taken to calling my 'Bobbie' which was quickly transformed into 'Barbie' by my crueller classmates. Jessica had taken me under her wing and when we were alone together, she took to calling me "Cindy" after her mother's collection of Cindy dolls and outfits which she had collected as a girl. Jessica told me that 'Cindy' suited me much better than Barbie, and we played for hours dressing the Cindy dolls in sexy and glamorous outfits.

As we grew through our teens and when her parents were out, Jessica liked to practice her make up skills on me and to dress me as 'Cindy'. On this particular occasion Jessica had come home from university and was due to go back in a couple of weeks for a formal ball. One of her mum's friends who owned a boutique specializing in prom dresses and ball gowns, had dropped of a selection of dresses which she thought might suit Jessica. Both of Jessica's parents were away for a long weekend, and with the help of a little corsetry and padding, we were very similar sizes and had both tried on all of the dresses. We had chosen quite similar gowns in different colours. Jessica looked absolutely stunning in her red satin off-the-shoulder dress with a fitted bodice and a full skirt over a taffeta under skirt. With her long dark brown hair, smoky brown eyes and red lipstick, she wore over-the-elbow red satin dress gloves, diamante earrings, choker and bracelet, and black stockings with four inch patent black stilettos. She had insisted that we were 'sisters', and that I should wear a very similar outfit, but in black. The stockings and taffeta skirt underskirt felt amazing against my freshly waxed legs as I teetered expertly about in my heels. Jess had managed to tighten my corset so that my upper body fitted the bodice of the dress perfectly with a modest but well-defined cleavage. My blue eyes looked really piercing and pretty, highlighted expertly by shadow, eye liner and false lashes, and she had painted a permanent red glow with theater lipstick on my pouting lips. Jessica had also highlighted and curled my long blond hair, which softly touched and teased my bare shoulders.

I longed to be going to the ball with Jessica. Instead, I had to settle for our girly night in as we shimmied downstairs into the lounge. I sat down elegantly on the couch, tucking my skirts under me, while Jessica went to get a bottle of chilled champagne and glasses from the refrigerator. We sat sipping our champagne as Jessica settled into an arm chair and started the first of our romcoms on her tv.

An unexpected arrival

We were just chilling nicely and getting a little 'squiffy' when we suddenly heard the front door open and a heavy bag be dropped on the floor in the hallway. "Hello! Is there anyone at home?" a voice called out.

"Oh my God, it's my brother Paul! He's not supposed to back on leave for another week or so," exclaimed Jessica as Paul walked into the lounge. Jessica leapt off the couch and flung her arms around her brother's neck, embracing and kissing him on the cheek. Paul was a Lieutenant-Commander in the navy and had been away for over a year helping to provide a military escort to merchant ships through a war zone. Jessica was hugely relieved to see him safely home after so long.

"Let me get a proper look at you little sister.. you look incredible. Are you going to a party? I'm so sorry I missed your 19th birthday last month," said Paul as he turned to look in my direction. "If you're going with your friend here, I think I might come along too." He walked over to me confidently, took my satin gloved hand in his, raised it to his mouth and gently kissed it. "You're a sight for sore eyes after 15 months at sea," he purred at me making full eye contact and looking every bit the gentleman in his navy uniform.

Jessica couldn't contain herself, she burst out laughing: "Down boy! Do you not remember Bobbie, my bestie from school? He...," she corrected herself, "... She is helping me plan my outfit for a formal ball in a couple of weeks' time. We got a bit carried away trying on dresses, and thought we'd have some fun together."

"I really have been at sea too long," said Paul with a wry smile on his face. He chuckled to himself and shook his head a little as he turned towards the door. "Ah well, will you girls at least have a home coming drink with me, once I've showered and changed into something more comfortable?" With that, he left the room, returning 20 minutes or so later, beer in hand and looking much more relaxed in a white t-shirt and gray jogging pants. He settled on the couch next to me, examining me intently as he took a mouthful of beer and started to recount tales of his time at sea.

We all chatted together for an hour or so, listening to his stories and laughing at episodes from the past. Jessica and myself had just finished the second bottle of champagne and Paul had finished the last of his four pack of beer, when the phone rang. Jessica took the call out in the hallway while Paul continued to chat and gently flirt with me in a gentle but teasing manner.

After ten minutes or so, Jessica returned to the room looking rather stony-faced and concerned. She explained that one of her best friends from university, who I had never met and lived on the other side of town, had just got back from the police station after having her purse and jewellery stolen by a mugger. She had returned to her apartment and really needed someone to sit with her and comfort her.

"Paul will you be an absolute angel and call me a cab, while I quickly change upstairs? I'll check on her and come back as soon as I can. Don't go away, I'm really enjoying our catch up!"

Just the two of us

After Jessica had left, Paul went to the kitchen and came back with some bourbon and two glasses with ice. "We're out of beer and champagne, this was all I could find," he explained as he poured out two generous measures, and sat back down on the left hand side of the couch.

Bourbon has never really been my drink but in the circumstances I didn't really feel like I could refuse, so I determined to sip it slowly and enjoyed chatting away with this worldly and rather charming man. After we had both finished two large doubles, the phone rang again and a very apologetic Jessica explained that her friend was absolutely distraught, and that she was going to have to stay over the night with her. I took this as my cue to leave and I instinctively sat forward on the couch and started to stand up. I felt dizzy with the after effects of the champagne and the bourbon, and hesitated, unsure whether I could adjust my balance and navigate the carpet in my heels. Paul instinctively sat forward and but his right arm around my waist asking me if I was ok. I shivered a little as I felt his warm breath on my neck and ear. He stroked my back reassuringly and gently brushed my hair over my right shoulder with his hand, stroking the top of my head tenderly a couple of times before returning his arm around me, and his hand to my waist. He leaned in and asked me if I'd like him to help me stand up. As he spoke into my ear, I felt his chin bristle softly against my shoulder.

I was lost! My legs now felt like jelly and any chance of me standing up and walking off in my heels had completely gone. I sat back on the couch to find his right arm still protectively around my waist. I turned to see this athletic man, tanned from his 15 months overseas, with the most wonderful pectorals and biceps accentuated by his tight white t-shirt, staring with genuine concern into my eyes. He instinctively lifted his left hand and stroked my head and hair before leaning in and kissing me on the lips. I returned the kiss and his lips lingered on mine for a moment. I pulled back slightly and asked him, "Are you sure about this?" He smiled and nodded to me and asked,"Are you?" As I nodded back to him, I felt his right hand slide up from my waist and gently but strongly cup my head in his strong and slightly rough skinned palm. As his head moved towards me, I felt my head being pulled firmly forward. Our lips met again, but this time I felt his mouth open as his tongue started to explore mine. Out of the corner of my eye, I saw my right hand with its long red fingernails start to explore his chest and biceps. As I returned my hand to his chest I could feel his heart rate rising, and his breathing starting to quicken. I slid my hand down pausing for a moment on his six pack, as I felt his hands exploring my body. I felt a strong hand squeeze my leg just above the knee before sliding up to my thigh. My own hand had slid further down to his inner thigh, and was now caressing his manhood through his loosely fitting joggers. It seemed the most natural thing in the world to then slide my hand inside his pants and his boxers, wrapping my hand around his substantial and now very erect cock. I popped it out of his pants and ran my nails upwards on his testicles, and along the shaft of his cock. As I did this, our lips parted for a moment and our eyes met. I smiled and enquired, "Is there anything I can do for you Lieutenant-Commander Sir?" Paul smiled back as once again, I felt his hand cup my head, and this time move it down past his flexing pecs and abdominals. I slid off the couch onto my knees as I opened my lips and slid his penis deep into my mouth. I heard him moan gently as his hips thrust upwards towards me. After a minute or so of sliding his cock in and out of my mouth, I slid my tongue down the outside of his shaft and started to suck on his balls. At this point Paul stood up and pulled my hair into a pony tail with his right hand before taking his cock in his left hand and thrusting it into my open mouth. He pulled my head forward and back while thrusting with his hips at the same time. His moaning grew louder and louder as his body spasmed with each thrust, before exploding in my mouth. I swallowed once, before more erupted into my mouth. I swallowed again, more came, again, and still more. Eventually as the flow stopped, I swallowed the last, and looked up obediently into his eyes. He gently returned my hair over my right shouldered and stroked my head, as he purred "Good girl.... Good girl." I felt wonderful, and so empowered that I had given such pleasure to this beautiful man.

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  • COMMENTS
5 Comments
JemmaJayJemmaJay11 months ago

I love this story. it really speaks to me as a trans woman. It's lovely to see a bit of romance mixed in with the eroticism. x

KatiwantsKatiwants12 months ago

So beautiful!!!

AnonymousAnonymous12 months ago

Loved this story. Tender and sexy. Looking forward to Part 2.

AnonymousAnonymous12 months ago

Looking forward to the next chapter.

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