After being caught by Jon, a family friend, whilst fully dressed as a female, my life was changing. He stood there with his throbbing cock inches from my face.
Anxiety was building. This was my first cock.
I opened my mouth and tentatively licked the tip of Jon’s glorious cock.
Jon’s murmurs told me he liked it. I carried on with my tongue licking at the tip of his cock. My hand wrapped around his shaft as I pulled his cock into my willing mouth.
“Baby,” Jon sighed.
I looked up to see him smiling as I swallowed his cock deep into my mouth. Jon started to slowly and gently fuck my mouth.
I felt his body stiffen and without warning he shot hot cum into my mouth. I gagged and pulled back in surprise.
“Baby, I’m sorry,” Jon said as he looked down. I instinctively took his cock back into my mouth sucking and licking his cum. Yes! I loved it.
When I finished cleaning his cock, Jon pulled me to my feet and kissed me, tongues dancing as he tasted his own cum. We stood and embraced, holding each other. My mind was a swirl of thoughts and emotions.
Jon spoke first.
“Are you okay?”he asked.
“Yes, yes I am,” I replied.
“Are you sure, I don’t want to push you too far too soon,” he said.
“I am ready, I want this. I could be your girlfriend.” Not knowing where that came from we stood in silence holding each other.
Jon asked if I was really sure, as he could make it happen.
“I think so,” I whispered back.
“Okay, let’s sleep on it,” he said.
I fell asleep on the sofa in his arms, only waking when he said I should go to bed.
I woke the next morning, still wearing my bra and panties when Jon came into the room with a cup of tea.
“Good morning,” he said. “How are you today?”
“I am good, thank you.”
“Do you have any regrets?” Jon asked.
Nervously I replied knowing my answer could change my life.
“No regrets,” I said.
“So Sam,” Jon said “Shall we go shopping?”
Jon laid out the clothes he thought I should wear whilst I showered. White skinny cropped Jeans, a white floaty top and matching lingerie and stunning D&G jewelled sliders.
I was amazed how tasteful the ensemble was. Jon explained we had lots to do and thought casual with flat shoes would be practical.
Jon was a very considerate man, who was the manager of a Championship soccer team. Quite the celebrity in the area.
“Are you sure about this?” I asked Jon. “People may talk.”
Jon assured me he was and with a little help would be convincing as a young woman, and that I should not worry, as he would get some help for me.
Unsure what he meant, we left the apartment heading for the city.
Jon explained he had confided in a friend who had offered to help.
Nicol was the owner of a high end beauty clinic and that’s where we headed first.
Nicol was a stunning woman of a similar age to Jon who clearly knew a thing or two about style.
Jon introduced us as we sat in her office.
Nicol said she was a long term friend of Jon’s and was excited to meet me and help “realise the dream”. We talked at length about likes and dislikes. Nicol said we should go out to the nail bar and do a manicure and pedicure whilst Jon made some calls for work.
We decided that Barbie Pink would be fun.
I was in heaven being pampered like a woman and having my first proper girly conversation without fear or judgement.
Nicol said that I was blessed with beautiful features and she could help me be the woman I wished for. We talked about hair; as mine was quite long, she thought extensions would help. Nicol went to the desk and booked an appointment with one of her stylists for a few days’ time.
Jon came out and said he had to go into the office and sort some things for the tour so gave Nicol his bank card and said he’d be back later.
Nicol squealed and said, “Let’s go, girl.”
We spent the whole morning shopping for clothes; so many colours and styles, I was exhausted. Just then the phone rang. It was Jon who said we should meet at the nearby wine bar. Nicol and I set off with our haul.
I was excited to see Jon as I had missed him.
When we arrived he gave me the biggest hug and kiss. My legs felt like jelly. We had a drink and thanked Nicol for her help. As she left, she reminded me of our appointment in a few days.
I wanted to get Jon home and show him how grateful I was. No sooner had we got into the lift going up to the apartment I was all over him, kissing him, telling him how happy I was and how I wanted him.
Once in the apartment we were on the bed.
I undid his belt, jeans and pulled them down exposing his rock hard cock. Without hesitation I had my pink lips wrapped around his cock, sucking, kissing and taking it deep into my throat.
Jon was moaning, rubbing his hand over my back and ass.
As I knelt up he told me to undress. No sooner had he asked I was naked beside him.
We kissed and fondled each other whispering words of lust.
I asked Jon to make love to me. Asking if I was sure, he reached for the drawer and took some lube. Expertly massaging my boi pussy with lube he slowly edged his cock into my willing hole. Taking it slowly he stretched me. Not sure if it was pain or pleasure I begged him to fuck me, my legs wrapping around his waist and he slid his shaft deep into me, fucking me with deep meaningful strokes.
I could feel his cock swelling and instinctively knew I was soon going to feel his seed deep inside. Jon thrust hard and came will all he had, emptying himself inside me. I pulled him close and kissed him as his weight came down on me and we lay, feeling his hot cum tricke out of my boi pussy.
Jon had made me his girl.
