Sweet Dreams are Made of These Ch. 02

I was showing Mrs. Annalise Anderson around the estate property when she took the initiative and probed my mouth with her tongue. She stripped off my clothes and revealed the camisole and panties I wore beneath my male clothes. Surprised at first, she then basically attacked me. She fucked me hard until I came inside her pussy.

"Jacque, that was very nice. I hadn't been fucked like that in a long time." Annalise panted as she was still mounted atop of me. "And I love your outfit. You know when I was first attracted to you, I always thought you were a bit effeminate."

That said, Annalise started to hump me again.

Annalise said she'd try to convince her husband to buy the place but he would say no. I showed them other places and then with her alone where we would fuck each time but resulted in the same negative purchasing result. I later found out that Annalise would tell her husband she didn't like the place just so I'd show her others and we could fuck. In the end, they bought the first place where I'd visit her when he was away. BTW, each time I met with her, she'd demand that I dress up for her which I did happily.

I told what happened the first and every other time with Annalise to Jennifer. She wasn't angry at all. In fact, it only made her horny. She made me dress up and fuck my brains out. "See? Women love guys in sexy lingerie!"

My sleep continued to be filled with different visions of me dressed in various types of women's clothing. Typically dressed in sexy or slutty outfits. I'd suddenly would wake up in bed with a panty full of cum. I hadn't had wet dreams since I was a teen. Now it's almost every night.

Jennifer made me start to shave everything. Not that I had a lot of body hair anyways. I was cleanly shaven which at first was embarrassing when I showered with the guys after soccer. My daily underwear had completely changed. I no longer wore any type of male underwear only panties. And even in the change room when I put my kit on for soccer, the panties I wore were women's but were black, cotton bikinis so it kind of looked like men's. I still was wore the GPS sports vest to track my fitness but now it felt more and more like a bra than a vest.

Jennifer coerced me to wear stockings and garters like she did. The feeling of rubbing our legs together especially when we were fucking was intense. But what followed boggled my mine.

"This is for you, Jackie." By now I was okay with her calling me by my girlie name rather than Jack or Jacque. Jenn presented me with wrapped box about two and a half feet long. It was about twelve inches tall and the same wide.

I lifted the cover and looked inside, then at Jenn and then in the box and then at my girlfriend again. She was smiling at me. Inside was a set of boobs. Big ones. With big aureole and big nipples.

"They are self-adhering so you won't need any messy glue or tape." Jennifer explained. "At first I thought I'd start you with smaller ones but then I thought what the fuck and got the biggest ones they had. Bigger than mine. They're K-cups!"

"Boobs? You want me to have boobs?" I questioned.

"Yeah! Two reasons. One, I'm tired of you not properly filling out your bras." She started. "And two, we get to shop for new bras! Just try them. I bet you'll love them."

I lifted one up in my palm. It felt pretty hefty, probably around four or five pounds. I took off the bra I was wearing then Jennifer helped position my new breast to my chest. It seemed to just suck on to me. As it hung freely, I could feel how it pulled downwards. With the second one attached, I understood why women needed support. I held each in my palms and felt the weight. I shimmied my shoulders. My boobs shook like jelly but remained securely attached to my chest.

Since most of them wouldn't fit, Jennifer suggested wearing a demi-cup, shelf bra to support my boobs from beneath. She helped me on with it and adjusted my boobs. I looked at myself in the mirror. The too small bra pushed my boobs together and form a deep cleavage. My nipples had to be about the size of red raspberries and protruded out uncovered by the bra cups.

Jenn hugged me from behind. I watched us as her hand snaked around and played with my new boobs. Her hand reached inside my panties and stoked my cock to full hardness. She literally threw me onto the bed and mounted me. Pulling aside her panties with one finger, she ran the tip of my dick along her slick slit before she sat down on it. She was hot, wet and tight.

With both her hands she squeezed my tits as she humped me. Suddenly, I started cumming inside of her but she was unrelenting. She didn't care about anything but self-satisfaction. My dick hurt so much as she kept on fucking me harder and harder and over and over. After her third orgasm, she finally collapsed on top of me. Our breasts smashed together.

Jenn made me wear my forms for the rest of the day. You could not sleep in them so I carefully peeled them off, cleaned them and stored them back in their box. I took a quick shower, made sure I was properly smooth and hairless and got ready for bed.

Jenn was waiting for me. She was wearing a black, silken, shortie robe with a tie around the waist. She had laid out my nightwear on the bed. It was a new, red satin babydoll with tied shoulder straps. The built in, underwire bra had lacy demi-cups. It came with a tiny string thong that would dig into my ass and control my hard dick. I slipped on the babydoll. It was barely long enough to cover my ass. I looked at myself in the mirror. I loved the outfit but still frowned. Jenn asked what was wrong. I said. "I'm a bit disappointed now that my cups are empty.

Jenn slipped off her robe to show me what she had on beneath. She wore a black, lace cami with a matching short skirt. It was transparent enough to see she wasn't wearing any panties beneath.

After an intense session of loving and fucking, Jenn fell into a peaceful sleep. Me, I had another dream.

It was dark outside. I was standing on a street with a single overhead street lamp randomly flickering light. I stared at my reflection in the window of a closed store. I wore a sheer mesh, white dress. Clearly visible beneath was my red bra and thong panties. Laddered stocking were held up by a ten strap garter belt. I looked down at my feet to see my red painted toes sticking out the fronts of an open toed sling back, stiletto heeled shoe. A careful look at my face showed whorish make-up with vibrant red lips.

"Honk!" I didn't see the car pull up behind me. I turned to see it was Ron from my soccer team. "Hey babe. How about a blow job?"

Suddenly, I was sat next to him in his car. His hands pulled my knees apart then crept under my hem. His fingers found my cock and pulled it out. Ron leaned over and kissed it. Then I felt his lips surround my knob and slide down my shaft. I started to shoot my load into his throat.

"Aaaiiiaaahhh...!" I screamed and sat up. I was back in bed. My undies were soaked by my cum.

Jenn turned over. "What's a matter, Jackie? Are you okay?"

"Yeah, yeah. Go back to sleep." I told her worried she'd discover my cream filled panties. I got up and went to the can to clean up.

The next morning, Jenn found me with a boner and panty-less. She looked at me curiously but said nothing. She crawled between my legs and sucked me until I fed her my cum for her breakfast. "Mmm... Cream with my coffee!"

After my morning routine, I got dressed in the outfit Jenn had laid out for me. I placed my new breast forms into position and supported them with a fiery red, too small bra. I had to readjust the straps and even then the lace cups barely held my huge boobs. Next was a red micro-string-thong. It was just big enough to cover my balls but left my cock hanging. Well it wasn't really hanging. It was getting stiffer as I dressed.

A sheer red garter belt with black lace trim. A tiny black bow marked the fronts with a five hook and eye closure in the back. The red seamed, fashioned stocking slide up my smooth hairless legs and the wide red welts were held up by six thick garter straps.

Jenn had left out one of her white blouses. Of course it was too small as I did up the front buttons that strained to hold close due to my huge boobs. I left the top three undone. The shirt was sheer enough to easily show my bra beneath. The skirt was a tight, stretchy mini that covered my garter clips and stocking welts as long as I didn't move or walk. There was a nice crotch bump in front as my hard cock pushed out the material.

I carefully stepped into the red mules she left out for me. I easily found my balance and took a few steps in the four inch stiletto heels. Instantly, the hem of my skirt popped up and not only exposed my straps and welts but my erect dick too.

"Wow! You look hot enough to fuck!" Jenn wolf-whistled. "But I think a couple of finishing touches."

She had me sit down and then started to apply make-up. She started with eye lash extensions and mascara and some shaded my lids. Then some foundation, shading and blush. She made me purse my lips and applied some lipstick.

While I started growing my hair longer, it was still pretty short. Jenn had a wig she once used for Halloween. She pinned the shoulder length, red bobbed wig to my head.

Jenn had a huge smile on her face. I think she was happy with the results. I turned to look at myself in the mirror and was shocked at the transformation. Honestly, I could barely tell it was me. And then with the long nails she glued on, I really felt like a girl. After she shaped them, she painted them a sparkly red to match my lipstick.

"Jackie, I think you're really enjoying being a girly-girl." Jennifer rubbed my hard cock through the thin material of my skirt. "Look how hard you are. "

In my heels, I promenaded around the room and made sure to keep my eyes on myself through the full length mirror. I couldn't believe the protruding bump made by my hard erection. I can't remember being that hard ever before.

Of course as I walked around, the hem of my skirt climbed higher and higher until some of my panty was exposed. I looked at Jennifer. She was literally panting; her eyes were as big as saucers. Dropping to her knees, she pushed my skirt up even higher and pulled out my cock. Forgoing foreplay, Jenn opened her mouth and took me into her mouth. A finger slipped beneath and jammed into my rectum. I started cumming and cumming and cumming.

I was spasming and shooting blanks but Jenn kept sucking me until my knees buckled and I fell back onto the bed. I laid there... On my back... My skirt pulled up around my hips... My panties pulled down... and my still hard dick sticking straight up and throbbing. The few dribbles still oozing from my pee hole were licked off by Jenn.

I thought maybe Jennifer would sit on my face and make me eat her pussy but she looked down at me and smiled. "Come on, you slut! Cover up your modestly and lets go."

Did I hear right? "Let's go." Let's go where?

I pulled up my panties in place and pulled down my skirt. I went to the living room where Jenn was waiting. My heels clacking on the hard floors as I took each step. My hem already crept over my stocking tops. Keys in hand, she guided me out the door and to the car.

It was a bright sunny day. I slipped on a pair of big, cat eye sunglasses just like those old style movie starlets as Jenn drove to locations I did not know where. We pulled up to a stop light beside a delivery van. Out of the corner of my eyes, the van driver look over, did a double take and smiled. Again my hem had climbed upwards over my thighs. I was pretty sure the crotch of my panties were showing. I expanded my chest and pushed my boobs out.

I soon realized our destination. The big mall. Jenn recognized my sudden anxiousness and told me. "Jackie. Relax. You look marvelous! Certainly a lot better than a lot of those dowdy housewives and moms that will be there. I bet every husband will have their eyes on you and want to stick their dicks in you!"

That really didn't make me feel any better.

The parking lot was half full and we couldn't park that close to the entrance. We got out of the car and I immediately had to pull down my hem. Then again after every half dozen or so steps. By the time we entered the air conditioned entrance, I basically gave up.

The first stop Jennifer took me too was "Intimates" lingerie shop. My mouth watered at the luscious selection of bras and panties and baby dolls on display. Jennifer signalled over a young sales assistant. "My girlfriend Jackie need some new lingerie."

"Hello, Jackie." The buxom blond clerk smiled. "I'm Vicky. I'm pleased to meet and help you. What are you looking for? Do you know what size you need?"

Before I could speak, Jennifer answered for me. "She's not sure of her size since she just got hew new bigger boobs. She'll need some very sexy outfits as well as some everyday things but not granny panties though."

Jennifer and Vicky continued to discuss my needs ignoring me as if I couldn't talk. Jenn walked around and selected items for me to try on. In the back change area, Vicky asked me to remove my top so she could measure me properly. She helped me off with my too small bra and gasped at my breasts. From behind and with my arms up, she wrapped around the measuring tape and wrote down my under breast size. She adjusted the tape over my big nipples but as she did, Vicky cupped and played with my boobs. For some reason, she had to take the measurement multiple times. Finally a panting Vicky told me. "Your cup sized is K or K+ for future reference. Please stay here. I'll bring you some things to try."

I exchanged the too small bra for a properly sized one; a red three-quarter, lace cup bra that would still match my micro-panties. So five bras, a dozen thongs, panties and G-strings, a few baby dolls and nighties later, we were ready to go. I couldn't even tell you how much it was since Jennifer just paid for it, albeit with my card. Bags in hand, Jennifer lead me to a dress shop where similar results occurred. Most of the outfits were very short or very sheer or both.

Finally shoes. She took me to a small boutique hidden in the back of the mall. The bored girl behind the counter perked up as we entered. She was a slender, dark brunette with small tits especially compared to mine. She was tall. Over six feet. I had to look up to her as she greeted me. "Hi. I'm Margo. Can I help show something to you?"

"This is Jackie." Jenn told her. "She needs new shoes. Black, white, red. At least two pair each. All must have heels at least four inches. Stilettos preferred."

With that Jennifer left. I remained, stunned at suddenly being left alone with this girl. She smiled and asked me. "What kind of styles are you looking for? Do you have any idea what you would like?"

Margo took me around the shop and showed me various types of footwear. We selected a couple for me to try out. She had me sit and measured my foot. "Size nine. Please wait I'm just going to the back to get your shoes."

I sat there nervously; anxious in case someone came in. Even then, I was rock hard with the thought of being caught in my girl clothes. I could do nothing as I could feel my pre-cum leak and wet my panties. I readjusted my hem downwards a bit more.

Margo returned with four boxes. She sat a stool in front of me and opened one of the boxes. She gently lifted my foot and leg up. Of course my skirt crept upwards and I was sure she could see between my thighs. She slipped on the first shoe. A nice, strappy, black sandal with a skinny four and a half inch heel. She buckled one then the other around my ankles. The backs had a black bow on it. "I think you will like these. They are sexy yet feminine and I think will show case your feet well. I'm assuming based on what your Miss. said that you are used to walking in high heels."

I looked down and agreed she was right. I placed both feet firmly on the floor before standing. I walked towards the slanted mirror and loved the way they looked on my stocking feet. Then my eyes bulged when I noticed how big the lump under my skirt was. There was little chance of hiding it. Even after I sat back down as discretely as I could, the tent was still obvious.

Margo's eyes were directly staring at my crotch. She licked her lips as she lifted my calf up to removed my shoe. Rather than letting me place my foot back down, she positioned it onto the sloped foot rest. My toes touched her pussy through her pants. By now, I couldn't be bothered to pull my skirt down. My hem was basically around my hips and my ass was half exposed.

I modeled more shoes and selected couple I thought Jennifer would approve of. As we continued to enjoy each other, Margo made sure to firmly place my foot between her thighs. She picked up another box. "I saved these for last. I think you'll just love them."

Margo removed the box lid and pushed aside the tissue. Each shoe was in its own cloth bag. She pulled the shoe out and my jaw dropped. They were indeed gorgeous. Sparkly red, open toed pumps with a seven inch, steel shanked, pencil heel and an inch and a half platform. She slipped them on my feet. I rose from my seat and walked around. The felt like they were made for me.

I placed my feet on either side of the foot stool and stood right in front of a seated Margo. She reached up and pulled my pre-cum soaked thong aside and freed my aching cock. Her wand wrapped around the back of my thighs and stroked my garter straps as she opened her mouth to take me down her throat. Her technique was amazing. Then she started to lap my ball sack. I spasmed and lost my balance causing me to fall back into my seat.

I guess I showed a bit of disappointment when Margo lifted my foot, I thought she was going to remove my shoe but instead parted her knees wide and used the sole of the shoe to hump against. She then used the heel of the shoe against herself. She was humping against it when it tore through the material of her crotch. She opened the tear wider and pulled her black panties aside. She rubbed the tip along her soaked, glistening slit and then slowly allowed all seven inches to penetrate her pussy.

I pushed my foot into her as she continued to fuck my heel. Her head shot back as she came. Her juices sprayed my foot and leg. "Aaauuuhhh...! Aaauuuhhh...! Aaauuuhhh...!"

As I extracted my heel, Margo shudder with each inch pulled out. "Oh my gawd! I came so hard. I've never done anything like this before!"

Just then Jennifer returned. She sniffed the air then looked at us knowingly.