Outing Ch. 02

Story Info
Sweetie's CD outing adventures continue.
2.9k words
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Part 2 of the 4 part series

Updated 06/07/2023
Created 04/27/2015
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grgy56
grgy56
1,564 Followers

Unbelievably, my girlfriend Lora found out about my crossdressing activities when I was polishing her shoes (and my knob). She had me dress up in some new lingerie and fucked my ass. My face was splashed with my cum which Lora made me "clean up" and swallow. Then after changing for dinner, she made me answer the door where Megan the pizza delivery girl saw me all dressed up.

Later, Lora and I ended up making love in our bed. I cleaned up the cream pie I gave her before falling asleep.

Over the next couple of weeks, Lora insisted I wear panties and bras around the house. She had given me some of her things to wear until last week after she had gone shopping.

"Sweetie, these might fit you better since you are a bit lacking up top." Lora handed me a couple of bags. "Go and change."

I went to the bedroom and looked in the bags. Inside were a number of bras; different types of bras. Some were full cups while others were demi-cups. One had a corset built in. They were all sized 38 AAA since I didn't have any breasts, but all were padded giving me a nice "B" cup.

She had also purchased a number of matching panties that would go with my new bras.

In another bag was a box. I carefully pulled it out to inspect. My mouth dropped as I read the box. "Breast Suction Enlargement Kit."

I didn't notice but standing behind me was Lora. "Do you like your gifts?"

"Yes, I like my bras and panties very much but this?" I asked.

"It is up to you, but it would make me very happy." Lora told me. "Those special padded bras are more expensive than normal ones."

So each day before I put on my bra, I used my breast pump to make my breast plumper. It seemed to work but the results didn't seem to be permanent. The kit included nipple pumps too. My nips became hard and prominent. If I wore a tee shirt, there were definite signs of pokies sticking out from beneath.

Lora had made me throw out almost all of my boy undies. Even going out, I mostly wore my girl undies everywhere except when I went to the gym to work out.

The weather was finally warming up. This Friday was a stat holiday and was supposed to be really nice. Our pool was ready for the summer and the deck area cleaned.

"Sweetie, tomorrow is shaping up to be really nice. Let's spend the holiday home in the sun instead of going out." Suggested Lora. I couldn't disagree with her if I wanted to.

Friday couldn't come fast enough. At 10 AM, it was already pretty hot. The sun beamed down on our back yard and would do so all day.

I was about to change when I realized I had no bathing suit. Lora already had a solution in hand and gave me one of hers. It was a neon yellow bikini. The bra had two reasonably sized cups that wouldn't make the difference if I had breast or not, but they fit better after using my breast pump for sure. There was a halter string that went around my neck and a string that tied in the back. I had trouble with that and Lora helped me tie the bow.

The bottom was a full French cut panty that tightly held everything in place. It was uncomfortable, but I tucked myself as best I could.

Lora looked great as always. She wore a new, white bikini, if you could call it that. Small patches barely covered her nipples and her Areola peeked from behind. Her bottom was basically a string with a slim sliver of material that was wide enough just to cover her pubes. Her wetness made it slightly translucent.

I wasn't worried about being spotted in the back yard. Basically we are isolated from either next door neighbour and the back was reservoir bush that would never be developed.

Lora and I spent the day tanning under the sun cooling off in the pool if we got too hot.

Laying on her tummy, Lora undid her top. However when I did it, I found Lora had tied a double bow and I would need assistance undoing it. "Um... Lora, would you help be untie my top?"

"Mmmm... I'm sleeping." Lora mumbled.

With no help to untie my bra, I laid on my belly and tanned.

We both enjoyed our day in the sun. Dinner on the deck consisted of a light chicken salad and white wine. My dessert was licking and lapping Lora's juice pussy.

Evening started to cool off with the sun below the horizon. We moved inside to cuddle and finish our wine. It was so nice. Lora told me "I am really enjoying having a girlfriend to share my time with, Sweetie. Especially a girlfriend with such a talented tongue and a hard cock. Just perfect!"

She gave me a kiss and a hug.

"Let's go to bed. Go put on your nightie for me." Lora requested.

I went to go change as Lora used the bathroom. Somehow I managed by twisting and contorting to untie my top, and easily pushed down my bottoms. I looked at myself in the mirror. "Shit!" I exclaimed. I hadn't thought about tanning while wearing my bikini. There were definite, contrasting tan lines showing. The bottom was bad enough, but the top definitely showed I was wearing a bra while tanning.

"Oh, Sweetie. So cute!" Lora smiled. "You tan beautifully. Look how dark you are where you weren't covered. You should always tan like that. It's so sexy."

Lora's voice of confidence made me feel better. And I continued to tan dressed in the days following.

I went to the bathroom to clean up before bed. The nightie was a soft pink lace babydoll top and loose boyshort panties.

Lora fucked my ass with her strap on doggie style only pulling my panties aside. I jerked myself off and shot my load inside my panties. Lora did not let me change as we fell asleep spooning.

Next morning, I found myself alone in bed. Lora had already risen. I smelled coffee in the air.

"Good. You're awake." Lora said bringing in a tray of coffee and some croissants.

We enjoyed our breakfast on the bed. Lora sat facing me cross legged. She wore no panties. Her pussy glistened with wet. I continuously licked my lips as my hard on tented my panties.

Lora moved the tray and pushed me on my back. She pulled my panties down just enough to uncover my cock and mounted me. She used her hands to massage my breasts as she rocked back and forth. Her head was back and eyes were closed.

"Oh Sweetie. You feel so good inside me." Lora moaned. "Oh, come inside me. Now!"

I started thrusting to match Lora's movements. Her pussy seemed to squeeze and pump me. It took moment for me to start shooting my load into her.

"Oh fuck, Lora! I'm cumming!" I screamed like a little girl.

"Yes! Cum inside me! Oh Sweetie, it feels so good!"

I gave Lora every drop of cum I could. Lora's cunt greedily sucked everything I could ejaculate until nothing more came out.

Lora leaned forward against me. "Oh Sweetie! You are such a great fuck." She started moving forward. "But now...!"

Lora kept moving until she placed her pussy was over my mouth. I could see her relaxed and like a tap, our cum came gusting out into my open mouth. I could barely swallow fast enough. Half of it splashed all over my face. Lora pressed her crotch on me and spread it around. I ate Lora until she came again.

Lora managed to slowly rise off of me. She went to the shower to clean up as I laid in bed. I could feel the wet cum start to dry and tighten my skin.

After she finished, Lora told me to go clean up and reminded me not to shave again as she reminded me for the past week. The stubble was starting to itch and bother me, but I heeded Lora's request.

After cleaning up and adhering to Lora's odd wish of not shaving, I went to the bedroom to find she had laid out some things for me to wear beside the nipple-breast pump.

The pump results were partially successful. My nipples maintained a rock hard point but although I managed to get my breasts to a minimal size AAA, the effects were temporary. Although it was temporary enough to fill the white padded bra Lora left for me to wear. The white thigh high cut panties held everything tight and the strip between my cheeks felt incredibly sexy.

The tight white cotton tee-shirt and hip hugging jeans gave me a real sexy shape. I put on some frilly, white ankle socks and my canvass runner before dashing down to get Lora's approval.

Lora was waiting for me in the living room. She wore a wide brimmed hat and sunglasses. Her white sundress with red roses on it was unbuttoned down to the third one showing off her buxom cleavage. She wore stockings and red high heeled mules.

"Sweetie, you look nice." Lora smiled. "Ready?"

I looked at her stunned. "Ready? Ready for what?" Lora hadn't given me any more information or instructions so I had no idea what she was referring to.

Lora stood up. In her hands were the keys to the convertible. I stood there trying to comprehend what this meant but she grabbed my hand and led me to the front door. Then it struck me.

"Lora! I can't go out like this!" I pleaded. "I mean you can tell I'm a guy in girlie clothes! This tee shirt isn't baggy enough to hide my bra!"

"You're right!" Was all that Lora answered. She pushed me out the door and locked it. I had no keys to get back in, so I ran to the car and jumped in the passenger seat. I crossed my arms and slumped down to try and hide as Lora slowly got into the car. She pretended to adjust the mirrors, pulled down her visor to check her lipstick and face and position her seat (which was a power memory seat anyways so she really didn't have to move it.

Satisfied, Lora pushed the start button and the car roared to life. "It's a lovely, warm morning isn't it Sweetie?" Lora said as she pushed another button. The roof started rolling back. "Now sit up straight and do your seat belt up."

Car in gear, I had no choice but to buckle up. The warm sun felt great and I began to enjoy the warmth, until I noticed the bright sun made my tee shirt near transparent; my bra easily showing through.

I covered my boobs with my hands.

"Sweetie! Stop playing with your breasts! Put your hands down!"

Lora drove slower than normal. She came to a full stop at each stop sign and even though there was no traffic, Lora made sure to check all ways were clear before proceeding. She slowed enough to be caught at every red light. Other cars around us were too low to see below the door line, but a number of trucks that stopped beside us could easily see inside. Fortunately, Lora had undone a number of buttons from the bottom of her dress and opened it wide showing her sexy stocking covered legs. She wore no panties.

Finally after driving for nearly an hour, we arrived. I had no idea where we arrived at. Lora shut off the motor and got out of the car. "Let's go, Sweetie!"

I looked around and saw no one but still with much trepidation, I opened my door and exited. Lora took me by the hand and to a store about a half block away. I looked at the sign in the opaque window. "T(He) G Spa"

We walked in and were immediately greeted by a woman. Her name tag said, "Tiffanie."

"Hello. You must be Lora who made the reservation." Tiffanie smiled. "And you must be Sweetie. Welcome to the G Spa. Thank you for coming on time. You don't know how many clients come in late and not care about other."

I looked at Lora, then at Tiffanie. I looked at her again. There was something I could not put my finger on.

"Yes, I am Lora. This is Sweetie. I made an appointment for Sweetie." Lora confirmed. "I believe it was the Princess A-package and included the special option."

"Yes, that is correct." Tiffanie affirmatively shook her head. "To review, it is an all-day special treatment for body, hair and make-up with hostess accompaniment. All the employees working here are T-girls, either pre-op or nearing pre-op or post-op. All are beautiful. All are here to make this a great experience for our clients. Any complaints, please let me know immediately.

"That was it! That's what was different about Tiffanie. She's a she...he...she..." I thought.

"Sweetie, here is your hostess, Cheryl." Tiffanie introduced. "Cheryl, please take good care of Sweetie."

Cheryl stood about 6 feet tall in four inch heels. Her body was perfect, legs were long, breast were full, blond hair pulled back in a ponytail cascading over her shoulder.

"Nice to meet you Sweetie." Cheryl shook my hand. "I'll make sure you enjoy yourself today."

"Okay, Sweetie. You are in good hands. I'll see you later." Lora waved.

"What! Wait! You aren't staying with me?"

"No I have a few errands to run. I'll be back when you are ready." And Lora turned to leave.

"Oh Sweetie. Please don't worry. We'll take perfect care of you." Cheryl and Tiffanie reassured me. "Come. Come this way."

As part of the package, I was lead to a warm, private dressing room to undress, but I didn't have to undress myself. I had already kicked off my shoes when my hostess, Cheryl carefully stopped me. "Sweetie. Relax. We do everything."

Cheryl pulled off my tee shirt over my head. "Oh what a nice bra you have one, Sweetie." Before tugging down my jeans. "And some sexy undies too!" She knelt in front of me. I used her shoulder as a brace to lift my feet up so she could free me of my jeans and socks. Then she pulled down my panties. My cock swelled slightly. "What a nice looking ...?" Cheryl looked at me and asked. "Do you have a name for it?"

"No, I never thought of calling it anything." I admitted.

"In that case, what a pretty cock you have Sweetie." She gave me a coy smile, looked around and then gave it a tiny lick and a kiss. Standing up behind me, she undid my bra hooks. "We're not supposed to... you know, but sometimes I get carried away."

"Oh my! What cute breasts you have." Cheryl grinned and cupped my titties. "And such pointy nipples too."

Cheryl helped me with my warm fluffy robe. Cheryl led me to a steamy shower area. The water was already flowing from the multi-head shower. She removed my robe and let me stand in the hot stream.

The gentle spray felt like miniature fingers giving me a massage. Then I felt a hand. Cheryl had undressed and was naked beside me. Her body was fantastic. Large firm breasts. Flat tummy. Trimmed bush. 8-inch uncut penis.

Cheryl made sure I was completely wet before shampooing and conditioning my hair. From behind, Cheryl arms surrounded me and soaped my body. Her firm cock nestled into my crack. "God, I wish she would fuck me." Her hands dropped lower as she paid special attention to making sure my penis was clean.

Cheryl moved around to the front. She pressed her breasts and cock against me as she washed my back. She poured more liquid soap into her hands and gave me a smile. One hand took hold of my erection while the other found my ass crack and hole.

As she stroked me, a finger pushed harder inside me. "Oh, fuck yes, Cheryl! It feels so good. Oh god, you're going to make me cum!"

Cheryl suddenly slowed to a stop. "No, not yet Sweetie. Miss. Lora gave us specific instructions. But..."

Cheryl moved to her knees in front of me. "Please don't tell anyone. Like I said before, we're not supposed to this." A hand reached between my legs and her finger resumed ass fucking me as she took my soapy cock into her mouth. Her head bobbed back and forth as her finger fuck my ass deeply.

"Oh Cheryl! I'm cumming!" And started shooting my load down her throat.

"Cheryl!" A shout from behind us. It was Tiffanie. "What are you doing? Miss. Lora gave us instructions."

"Uuuh... I was just making sure Sweetie was clean enough to eat?" Cheryl tried to make some lie up but the bubbly cum dripping down her chin was evidence to the contrary.

Unbelieving, Tiffanie informed us that the bath was ready. Cheryl wrapped my head in a towel and guided me into a tepid salt bath. She applied some facial mask and placed something onto my eyes.

"Sweetie. I'll be right here if you need something. Please just relax." Cheryl told me.

I laid soaking in the tub but could hear Cheryl and Tiffanie talk quietly.

"You know we're not supposed to do that stuff. And Miss. Lora gave us instructions."

"I know. I'm so sorry. Sweetie is so cute, I couldn't help myself."

"Yeah, I know. I'd do the same thing. Just be careful!"

I nodded off asleep.

grgy56
grgy56
1,564 Followers
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  • COMMENTS
5 Comments
cdCindy1cdCindy1over 5 years ago
loved this chapter

I wish I had a nipple-breast machine. I think I need to shop for one. It sounds wonderful. I would love for my wife to splurge and treat me to a make-up and spa day. Sounds wonderful. Can't wait to read the next chapters.

TiffanyLaPerouseTiffanyLaPerousealmost 9 years ago
Gorgeous

Lovely story, quite a day. Xxxxx

Tiffany

BrendaNWBrendaNWalmost 9 years ago
so nice

Please continue.. Love to see what happens next... I believe there are trans friendly places around, I think you have to check online or call around to see about body and even hair removal for us non genetic girls... I believe the staff is typical..

DaveXX80DaveXX80almost 9 years ago
Terrific!

Great turn in the story. Oh if only places like that were around.

AnonymousAnonymousalmost 9 years ago
Loved it!

I often think of myself as "Sweetie" when I dress up. The day at the spa is a great idea, wish it would happen to me.

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