New Pleasures for My Friend

For many years I'd had a fascination for breasts.

Big breasts.

I mean really big breasts.

Breasts that would make Dolly Parton look at them and say, "Wow girl! They are magnificent!"

Of course, loads of women like the idea of having larger breasts as it makes them feel more feminine.

And men like the idea of fucking a women with big breasts as a fantasy fuck.

The difference is that I was a man who wanted to have big breasts so I would feel more feminine!

Ever since I'd left home and had a place of my own I had started to dress up more and more often. I think all cross-dressers need to find their inner woman. It appears that my women wanting to get out wanted to have BIG tits. And BIG hair. And BIG make-up.

This was how Nikki was born.

Nikki loved to show off and tease. When she found on-line chat rooms, she was in heaven. I let her become an ever larger part of my life so much so that for a period, Nikki was taking over my life. I had ups and downs but one day I finally realised that I was happiest when I let Nikki become the dominant part of my life.

I was making a small amount on various websites and had quite a following on sites like Patreon. I made a promise to myself that if I quit my real world job and focus on making Nikki come to life 24/7 and earned £5k from my various income feeds, that I would treat myself to those super sized tits I'd wanted for years.

To ensure I dedicated myself to this challenge, I knew I had to make major changes to my life. I quit my home town and found a place to live in London. I knew that it would be a struggle, but it was something I had to do.

And that's what I did.

It took a few weeks for things to settle down, but once I had sorted out the apartment, I focused on my challenges and treated it like a new job. I set up a routine of self improvement to get myself in good physical and mental shape. Every day I set myself targets and objectives. I soon had a backlog of cute photo sets ready to post on my Patreon page and plans for setting up various side projects.

As I spent more time on my work, the results improved.

As my results improved, I had more clients.

As I got more clients, I became more motivated.

As I became more motivated, I spent more time on my work.

As I spent more time on my work, the results improved.

I was so happy that it stopped feeling like work. I was enjoying everything about my new life and was becoming more and more successful. Before I knew it, I was approaching being in London for six months. I had tried very hard not to see how much my projects had been bringing in, but come my six months anniversary, I was nervous to check out how I had been doing.

The day arrived and I didn't have £4k in my account.

I didn't have £5k.

I had over SIX THOUSAND pounds!!

I couldn't believe it. I was so proud of myself!

Now, did I have the courage to go through my private wager?

Well, let's just say that as I write this, I keep getting distracted when I look at the keyboard by the sight of my bountiful new cleavage!

I now have the hourglass figure that I've been dreaming of.

And it's wonderful!

I'm so happy and the surgeon was terrific. He had warned be about the scaring would last a few weeks but once the swelling went down, the scars would soon disappear.

I knew that I wouldn't be able to keep my on-line profile active whilst I was recovering so I had stockpiled plenty of photos I could post in the interim. It was so difficult not letting all of my friends know where I was and why I had been so quiet, but it was for the best. My projects continued to thrive using my pre-operation pictures, but I couldn't wait to share my new body with my on-line friends.

When I felt I'd recovered from my procedure, I decided it was time to return to work. Unsure if I should be conservative with my first new set or let the world see my new assets, I went for something in the middle. I chose a cute animal print, low cut top and a black PVC pencil skirt that I had been saving for a special occasion and my favourite straight, purple wig.

The photos turned out so much better than I could have dreamed of. When I posted them I made no mention of these being my new breast's first outing.

I received many compliments and no one seemed to realise that they were no longer looking at my fake breasts. I had suggested that they were boobs from a new supplier to the market. Well, the story was true wasn't it?

My friend Vinny sent me a little compliment and queried how they felt and I could only tell her the truth that they felt very heavy. Well, I wasn't used to having boobs twenty four hours a day, so they were beginning to feel heavy. I loved going to bed naked and just looking at how they settled on my previously flat chest. I was so happy with my decision!

But I needed to see how they coped with a little bit of action, if you know what I mean?

I didn't want to have a random pick-up in a bar and I knew so few people in London.

Who should I let be the first?

And then it came to me ...

... Who better than Vinny?

She had always encouraged me to do what would make me the happiest and, despite the fact we'd only spoken on-line, she seemed a lot of fun.

Now, how could I make it all happen?

That was how I hatched the plan to invite her down to my new apartment. I had considered opening the door with my new tits out, grab her by the hand and drag her to my bedroom before ravishing her.

Too desperate?

I think she'd have run a mile if I'd taken this approach.

No. I needed to seduce her and treat her like I'd like to be treated.

I took some more money out of my projects and went shopping. I headed for Knightsbridge and my favourite lingerie shop. La Perla had such sexy collections and was so much classier than Victoria's Secret. I chose matching set of silk bra, knickers and suspender belt set. White for my virginal friend and red for slutty old me.

It was so exciting to have to buy the largest bra cup size for myself and I loved going to the fitting room with the attendant. She couldn't take her eyes of my tits as I removed my blouse. I'm sure she didn't need to squeeze my tits so much as she manoeuvred by breasts in to the bra cups, but I'd be lying if I said I didn't enjoy it. Of course, we both decided that the bra fitted perfectly. I had wanted to wear it out of the shop, but the assistant said that wouldn't be allowed.

As she turned me around to unclasp the bra, in the mirror I caught her staring at my semi-naked body. I turned around, letting my breasts fall from the bra cup and cupped them in my hands, holding them up for her to see them.

"Would you like to feel them?"

"Yes, that would be lovely."

Nervously, she reached forward and replaced my hands with her hands. She was very gentle as if she was handling something very precious.

"They are quite magnificent. Would you mind if I ...?"

I knew exactly what she wanted to do.

"Please do."

Soon her lips were suckling on my right nipple whilst her fingers were tweaking the right one. I held her head in place as she made love to my new titties. I couldn't believe how much pleasure I was getting from this stranger playing with my new love pillows. And I was so pleased that I was getting plenty of sensation from them. To reward this lady for being the first person other than me and the surgeon to fondle my tits, I slid my had between her thighs and began to play with her very wet pussy. As she ground her face between my new tits, I slid one, then two fingers in to her pussy. She was so excited it wasn't long before she was grinding her groin in to my fingers and chewing on my nipple to stop her screaming.

Just as I felt she was about to cum and scream the place down, I pulled her face up and gave her a big passionate kiss. She had her eyes wide open as she came in my hands. I could feel her juices running down her thighs as she collapsed against me. I withdrew my fingers from her pussy and brought them up, offering them to her to lick clean. She frowned at me wondering what I meant for her to do. I played my finger along her painted lower lip and then slide it between her lips.

This ultra conservative lady had just been brought to a climax by a women for the first time and was now licking her own cum. I can only imagine what she did when she went home that night, but I bet right now she is dreaming of making out with a big-tittied woman.

Straightening herself up the assistant realised what had just happened.

"I'm ... Erm ... I'm so sorry Madam. That was very unprofessional of me. You will accept these purchases as gifts of the house won't you?"

"That's very kind of you. Perhaps next time we'll have time to try out other items from your collections. I do need some more knickers. Perhaps you'll be able to help me choose something special."

"That would be my absolute pleasure, Madam."

She blushed like a 14 year old virgin after her first kiss. So cute!

Gathering up the two sets of underwear, we headed back to the counter for them to be packed.

"Your friend is very like to receive such lovely gifts. She must be very special."

Despite only having a had job from me just minutes before, she sounded almost jealous. But looking back, she was probably just envious. If only she'd known that later that day it would be Vinny pulling on this sexy underwear.

"Until next time." I said, giving her a big wink and stroking the back of her hand as I picked up the parcel, "You take care."

At the door I turned back to the counter to see her blushing with her hand between her thighs. She would be dreaming about me tonight!

I couldn't wait to get home and get everything ready for an exciting night. I tidied the place up and ran the Hoover around the place. All the washing up was put away in the kitchen and I cleared the radiators of my drying underwear. Once the place was as perfect as it would be, I poured myself a glass of red wine whilst I left the bath to run.

A little sultry music on the hi-fi and I stripped off before getting in to my bubble bath. Out of the corner of my eye, I caught a sideways look of myself in the bathroom mirror. Even three months after the enhancements, I still wasn't quite used to my new figure. I couldn't help but pushing them up, leaning towards the mirror a la Marilyn and blowing myself a kiss. I knew that I would fuck that girl in the mirror if I could!

I lowered myself into the bubbles and felt the stress of the day flow out of me. My breasts and knees were the only features poking out of the water. Not even my erection was making an appearance through the bubbles. Once I got to the bottom of my wine I soaped my body all over paying special attention to my long legs, my new boobies and my groin. Hey, if I played my cards right tonight, I wanted everything to be just right.

Before the water got too cold I was out of the bath and towelling myself down before dowsing myself in baby talc. I'd left plenty of time to apply my make-up. I'd decided to base my outfit on Pauline, one of my favourite computer game characters. I already had my new red underwear sorted and had a short red dress that I'd been dying to use in a photo shoot. I knew that the spaghetti straps and plunging neckline would make the most of my new assets. My hair had grown out since I'd moved to London and at the moment it was an a beautiful auburn red shade. Now all I had to do was apply red nail polish to my fingers and toes. Whilst it was drying, I started on my face. Once the foundation was in place I began on my eyes. I was well practised with my lashes. As we were going out for a meal I toned it down from my on-line persona, but I couldn't resist go for plenty of body. After a couple of layers of mascara, I was ready to complete the dusky eyes I knew men loved. And then my favourite part, applying my lips. Plenty of shape and a deep, DEEP red colour that no red blooded man has yet been able to resist. I liberal squirt of Poison perfume in all the right areas and I was ready to begin to dress.

I started with the suspender belt, attaching it around my waist before sliding each of the red stockings on. I do love the feeling of new nylons on smooth legs. No matter how often I do it, it gets me excited. The red silk knickers I then pulled on had to be carefully positioned to hide my baby erection.

"Don't worry" I thought to myself as I tucked my cock between my buttocks, "You'll be getting plenty of action tonight!"

Next was the bra which had aroused the shop assistant so much. As I settled my boobs in to the cups and looked at myself in the mirror, I could see why she couldn't keep her hands off me. Perhaps if my on-line ventures start to run dry I could get a job at La Perla? I have no idea what the pay is like, but the perks must be good. Plenty of samples. Surrounded by sexy underwear. Helping women select and fit their next underwear. There are worse jobs!

Well, I couldn't stand here all night checking myself out in the mirror. I did shoot off a couple of snaps for my personal collection. If my Patreon friends ever saw the pictures that didn't make it on-line they would be staggered! Time to squeeze myself in to the dress. Yep. I looked as hot as I hoped I would. The four inch heels were by the front door ready to step in to on the way out. They should be fine. I didn't want to look too tall and I hoped there would be dancing at some point.

After pouring myself a glass of wine I walked around the apartment like a virgin waiting for their first date. I paced up and down, constantly checking the phone for missed calls.

And then the door bell rang.

I ran to the door and flung it open.

There was my friend Vinny.

Despite chatting on-line many times, I had no idea what to expect ...

A bit older than I had pictured in my mind, but looked in pretty good shape, if a little nervous. Before saying anything, I threw my arms around his neck, pulling him in to a big hug. I was relieved when he returned the hug. Obviously he wasn't disappointed with the old bird in front of him, so I planted a big smacker on his lips.

No tongues ...

... not just yet ...

Eventually we broke our hug and Vinny held me at arm's length whilst we introduced ourselves to each other. Having giving him such a big welcome and a kiss, I was quite relieved that it was Vinny and not a cold caller who had a lucky feel!

I led the way to the lounge and over a couple of drinks we reminisced over the years we had known each other. We had more in common that we knew and in a short time, we had put the world's problems to rights. We had been getting on so well, I had forgotten that we still had to get something to eat.

"Time for dinner," I said, "Come on Vinny, let's go get you dressed. We're going to show these Londoners how to have a good time."

I grabbed his hand and pulled him out of his chair.

"Have you brought anything with you to change in to?"

I could see that he had no bag with him, so I already knew the answer, but I thought I'd tease him to see if he was up for a bit of fun.

"Erm. No I haven't Nikki. I was going to wear this. Won't it be smart enough?"

I'm sure Vinny knew that wasn't quite what I meant, so I pushed my luck.

"Oh you look very handsome, but I thought you'd want to come out with me as Vinny."

He began to blush and looked flustered.

"I ... I don't think I'm brave enough Nikki. I don't mind dressing at home, but I've never been out dressed as a woman. Is that a problem?"

Oh well. Perhaps next time I'd persuade Vinny to join me walking the streets of London. Hiding my disappointment, I broke in to a big grin, grabbed his hand and led him to my bedroom. I'd left his gift on the bed, still wrapped.

"Go on Vinny. Open it."

He looked genuinely shocked by the gift.

"Are you sure Nikki? These cost a fortune!"

"Of course I'm sure. My Patreons have been very generous lately and I thought I'd treat you."

I watched as he opened the box to find the sexy white lingerie set I had chosen for him. As he fingered the silk, I knew exactly what was going through his mind. "So sexy. I wonder what this would feel like against my skin. Will it look good on me?" I knew what he was thinking as it was the same thoughts I have had when I've been bought sexy underwear.

"Do you like them? They're part of the Spring Bride Collection."

I didn't really need to ask him. The look on his face made it obvious that he wanted to try them on. I couldn't wait to see how good they would look on him.

"They are gorgeous Nikki. Thank you SO much."

Vinny pulled me in to a big hug which I had to break off as I was keen to get a glimpse of Vinny in her underwear.

"Well come on Honey. Let's see how good you look in them."

He stood there for a few seconds, unmoving. I don't know if it was because he was shy or overcome by the situation. To get things moving along, I decided to take control and began to unbutton his shirt. I pushed it off his shoulders and left him to remove the shirt whilst I went for his trousers. I was interested to see if he had travelled in women's knickers or boring old underpants. I was excited to see that he was wearing some sexy transparent black knickers. Hey, there was hope that I could Vinny to explore her femininity more and more!

Now she was naked in front of me, I struggled to keep my hands off her silky body.

"I see that you keep yourself nice and smooth."

I couldn't keep my hands off her legs and ran my fingers up and down her smooth thighs. On my knees in front of her, I couldn't help but notice her cock was showing signs f excitement. A little drop of pre-cum was apparent on her cock head. I did consider leaning forward and taking her cock between my lips and giving her a quick blow job, but I've learned that sometimes I need to show some self control.

Well, only a little control!

"Can't have this leaving a stain on your new knickers."

Rather than sucking her off, I squeezed her cock head and licked her pre-cum of my fingers.

"Mmm! Sweet!"

Before Vinny could back out of the situation, I reached on to the bed for the knickers and invited her to step in to them. I slid the silk material up the long legs in front of me. Me attention was having quite an effect on Vinny as I was now faced with an erection pointing towards the ceiling. Despite desperately wanting to play with the lovely sight before me, I gently pushed it back between Vinny's thighs and trapped it inside her new knickers. I wanted to make sure that I had done a good job so turned Vinny around.

Wow! Her ass looked good with the white silk hugging her buttocks. How could I not give her ass a quick squeeze?

"They look good on you Vinny."

And they did!

"Oh, they feel good too!"

Now how about seeing how much natural cleavage we could muster?

"Hold your arms out."

Obediently Vinny held her arms out and I slid her new bra along them. The cups were holding her pectoral muscles in place. To emphasise what she had, I squeezed her boobs in to the bra and couldn't help noticing she had cute little curves. Not bad!

I spun her around again so I could do up the bra's clasp. Looking over her shoulder I could see Vinny checking herself out in the mirror. Standing beside her with my dress struggling to contain my new beauties, her eyes switched from her boobs to mine and back to hers.

Leaving my comment ambiguous, and leaving Vinny to decide if I meant her new bra or her breasts, I told her,

"Just the right size don't you think?"

"They're perfect Nikki. Perhaps next time I'll bring some fake boobs like you to give me more curves!"

Bless her!

She still hadn't realised that she was looking at real flesh and blood. I couldn't wait to see her reaction when it sunk it then those mounds on my chest were the real thing.