Dan Becomes Dawn – Part 3

By Kathi Jo Daniels

Chapter Fifteen: Back to Denver
Friday, September 17, 2004

I rose Friday morning, showered, shaved, put on a bra and panties, and applied makeup. I selected my navy-blue floral V-neck dress and white sandals.

On the drive back to Denver, I thought about what Diana had told me about swinging. I didn’t know anything about it and couldn’t form an opinion, but I was very surprised to learn that Mark and Nancy were swingers with Roger and Lisa. It made me think about my interactions with both couples the prior weekend. Had they been sending signals that they might want me to join them? I decided to play it by ear and see what unfolds.

I arrived at Roger and Lisa's shortly after three o'clock. Roger answered and greeted me with a hug and a soft kiss. "Welcome back, Dawn. You certainly look cute in that dress. Come on in, I’ll get your other suitcase."

"There’s also a bag with a partial bottle of vodka and some wine. Would you please grab that as well?" I asked.

"Certainly," he responded.

Lisa met me in the foyer with a hug and a kiss, our breasts meshing together, which thrilled me. "Hello, sweetie. Welcome back. You’re beautiful. I can’t believe how feminine you’ve become."

"Thanks. I’m forever grateful that you’re so accepting."

I wheeled my suitcase to the guest suite and unpacked what I planned to wear for the next two days. Roger came in with my second suitcase and put it on the other luggage stand. I knew I wouldn’t need anything from that one until Sunday.

"Thanks for bringing that in. You can have all the alcohol. I can't take it with me."

"No problem. When you get settled, come on into the family room."

I hung my dresses to let the wrinkles fall out and joined Roger and Lisa in the family room. Roger had poured me a Martini.

“Cheers. Here is to another great weekend with wonderful friends!” I hoisted my glass, and we touched rims.

“Hear! Hear!” they both responded.

"We’re discussing options for dinner. Do you have any preferences?" asked Lisa.

"Either tonight or tomorrow, I insist on taking you to dinner, my treat, and we’re not going to some hamburger joint! What do you have planned for tomorrow?"

"Nothing scheduled, just hang out, maybe see if there are any interesting football games, whatever comes to mind," answered Roger.

"Why don't we do something casual tonight and go out tomorrow? We can make reservations at one of the nicer restaurants. I hope you won’t be upset if I need to wear my cocktail dress again. I only brought one nice dress with me!"

Lisa smiled. "That’s a beautiful dress, and you should wear it again. Of course, that means I’ll have to dress up as well. I haven’t done that in quite some time. It’ll be fun."

"Which of the restaurants would you prefer? Don't be skimpy, this is on my expense report," I offered.

"We can give that some thought later; how about something to eat?" asked Roger.

We moved to the kitchen. I opted for Chianti with dinner. I couldn’t manage many Martinis.

"Here’s to wonderful friends!" I toasted them.

We clinked glasses and sipped.

Lisa went to the kitchen cupboard, retrieved her ruffled pastel pink apron, and helped me with the back tie. “You can wear my apron again!”

“Thanks, Lisa!” I laughed and gave her a hug and a kiss.

Roger chopped a salad, heated some meat sauce for spaghetti, and toasted garlic bread. The same meal we had last week.

After dinner, we all pitched in to clean up and put everything away. I removed Lisa’s apron and returned it to the cupboard. Roger poured me another glass of wine, and we retired to the family room.

Chapter Sixteen: Plans for Tomorrow
Friday, September 17, 2004

"Before we get too deep into our drinks, where do we want to dine tomorrow? I remember several options. Ocean Prime, Shanahan's, Del Fresco's, Maggiano’s, Ruth's Chris - what is your pleasure?"

"I vote for Ruth’s Chris," said Lisa.

"That works for me!" said Roger.

I laughed, retrieved my cell phone, called Ruth’s Chris, and made a reservation for five o'clock on Saturday, tomorrow.

"We’ll take an Uber. That way, we won’t need a designated driver. We can party like rock stars!"

"Okay. We have all that taken care of. Now, we’re dying to know. How did your trip go? Was it a success? Did you and Diana have a good time?" asked Lisa.

"The trip was fine. The property looks promising. I sent my report to the partners last night, and they’ll negotiate the pricing.” I took a sip from my wine and dismissed that subject. I knew that wasn’t what they wanted to hear! “Diana and I had some great times together. She’s so very accepting of Dawn. During the day, I’d be Dan, but Diana insisted on Dawn in the evening.”

Lisa grinned. “Excellent! So, are you two officially an item now?”

“An ‘item,’ for sure! Not positive if it’ll be monogamous or permanent, but I hope it will be fun and rewarding. I’m looking forward to next weekend when I meet her at her parents' home in Kansas.”

Lisa laughed. "I’m thrilled for you. Diana is a very wonderful person. If she accepts, you two can have a delightful time."

Lisa came over, sat beside me on the loveseat, and asked, “Have you ever done any swinging?”

“No. Diana mentioned that Nancy and Mark introduced her to the practice and that they swing with you and two other ladies.”

“Would you be interested in participating with us?”

“This is new to me, but I am intrigued.”

“As Dawn, would you like to do girl-on-girl?”

“Oh, yes! That would be wonderful!”

Lisa removed her shorts and panties and laid back on her recliner.

I knelt between her legs and buried my face in her pussy, swirling my tongue around her sensitive clit. Her breath became short and rapid. She pulled me deeper into the warmth between her thighs. “You are wonderful,” she moaned, her back slightly lifting off the recliner as she pressed herself into my face. I alternated between long, slow licks and quick, pointed thrusts of my tongue, finding a rhythm that left her writhing beneath me. Finally, she came with a loud cry, her legs trembled and shook, the muscles in her thighs contracting and releasing in an uncontrollable rhythm. I continued to lap at her, teasing her through the orgasm until she gently pushed me away, completely spent.

"Oh, my goodness, that was fantastic! I’m spent. What a wonderful experience! Thank you." She pulled me into a big hug and passionate kiss. “You’re incredible.”

"What a beautiful experience. I’m thrilled you pleased Lisa. Thank you," added Roger.

Dawn had just orally satisfied one of the most beautiful women Dan had ever known.
Think of having a raging hard-on!

“Since you have transformed into such a beautiful woman, you will want to know how to satisfy a man."

“Diana told me the same thing.”

“Would you like to try giving a blow job?”

"I have never done this, so I am not sure."

Lisa jumped up and ran to the master suite, coming back with a lifelike dildo. I wondered why she would have a dildo, but I didn’t say anything. She went to the kitchen and cleaned it with vodka. Returning, she presented it and suggested I take as much as possible. I opened my mouth, and she gently inserted the dildo.

"Open wide and let the dildo slide deep into your throat."

"That's a good girl!" she cooed approvingly as she moved the dildo back and forth, in and out. "Now you have the idea."

She continued to pump the dildo in and out of my throat for a few moments, then withdrew and announced, "I think you get the idea. Now for the real thing?"

I thought back to the conversation with Diana when she fed me my cum.
Her comment “Yes, I think you might eat more cum in the future” was becoming true.

"Roger, would you like to be my first?"

"Before we start, you should take off your dress."

I unbuckled my sandals, stood, unzipped my dress, stepped out, and laid it over the back of the loveseat. Standing in my bra and panties, I felt exposed. I recalled Diana stating that at some point in the future, I’d be pleasuring a man. Well, here I am.

"Roger, why don't you sit on your chair and let Dawn kneel? That would be more comfortable for her."

Roger removed his shorts and briefs and sat on his recliner. His penis was standing at attention! Lisa was right beside me, offering encouragement and suggestions. “Now take him into your mouth, but just the head at first. Suck gently and use your tongue.” As I bent forward, she stroked my back to urge me on.

I knelt and extended my tongue, licking a broad stroke up the underside of his shaft. He let out a low groan at the sensation. Encouraged, I swirled my tongue around the head, lapping at the bead of precum that had formed at the tip.

Doing the best I could, I wrapped my lips around Roger’s cockhead, giving it a soft suck. I swirled my tongue, eliciting another moan from him. Slowly, I began moving my head, taking a little more of him into my mouth with each downward motion.

“That’s it, Sweetie. Nice and slow,” Lisa encouraged. “You’re doing great. Remember to breathe through your nose. Relax your throat to take him deeper.”

“When he starts to cum, keep sucking and swallowing. Don’t stop until he finishes. The salty taste and texture can take some getting used to, but I know he loves having the cum sucked out of his cock.”

After pumping back and forth for a few moments, Roger began to convulse, shooting his cum into my throat. I swallowed and swallowed, but there was more than I could manage, and the overflow dribbled out onto my chin. Roger finally pulled back, and I sat up straight.

Lisa came to me. "You did great! Did you enjoy that?" She used her finger to wipe some cum off my chin and fed it to me.

"WOW! Yes, I think I did enjoy my first blow job! Roger, was that satisfying for you?"

"You were fantastic. I can’t believe this was your first. I’d enjoy that again!"

Lisa took a warm washcloth and wiped more cum from my chin, then cleaned Roger.

I sat up, found my glass of Chianti, took a sip, gathered my dress and shoes, excused myself, and went to the bedroom. After hanging my dress in the closet, I repaired my smeared makeup and lip gloss. Put on my red baby doll with a G-string and padded back into the family room. "How do you like this?"

"Oh, wow! That’s beautiful. You’re very sexy!" Lisa gushed.

Roger had pulled up his briefs and shorts while I was gone. "Would you like me to buy you a drink, Miss Dawn?"

"Please just refill my Chianti if you would."

Roger poured a full glass and handed it to me. I took a sip and asked, "Am I dreaming, or has this been a wonderful evening?"

"Come sit on my lap, you little sexpot.”

I sat on Roger’s lap. This is all new to me, but I’m excited, with a raging hard-on that is barely being contained by my G-string. Okay. It’s not being completely contained! I can feel Roger’s powerful hard-on pressing into my butt.

Roger began caressing my breast forms. “Do you like that?” he asked.

I leaned back and gave him a passionate kiss. I’d never done that to a guy before!

“Would you like me to introduce you to sex as a woman?”

“I think that might be wonderful!” I fear I’d gone into the abyss.

Lisa retrieved her dildo and instructed me to bend over the back of the loveseat. She coated the dildo with KY jelly, flipped my nightie out of the way, pulled the G-string aside, and gently slid the dildo into my anus. More emotions. Internal arguments. What the hell was I doing? I thought I was a man. I’m being introduced to sex as a woman. It was painful at first, but after she had the dildo beyond my prostate, it became a pleasant feeling. She probed back and forth until I gasped, and my knees buckled.

Removing the dildo, she took a condom, stroked it onto Roger, and let him penetrate me. Roger pumped several times until he convulsed, and again my knees buckled. He withdrew and took a towel to remove the condom and discard it in the trash. I held on to the loveseat for a few moments until my knees could support me. Lisa took another towel and wiped the KY jelly from my butt and hugged me. "How are you doing, Sweetheart?"

"I’m doing fine. That was euphoric. Thank you."

I pulled up my G-string, went to Roger, and hugged him. "Thank you for being the one to take my cherry. It was a wonderful experience."

Roger gave me a soft kiss. "Thank you for letting me be your first. I’d love to do this again."

I gave Lisa a big hug. “This is all new to me, but I think I could learn to enjoy it.”

We all sipped our drinks and relaxed for a minute, hugged and kissed, put our drink glasses in the sink, and retired for the evening.

Sleep didn’t come immediately. What has happened to Dan? Will he ever come back? Has Dawn taken over Dan's life? Has Dawn become bi-sexual? Does Dawn want to transition? These questions kept rolling around in my head. None were answered.

Chapter Seventeen: A Time to Relax
Saturday, September 18, 2004

I woke Saturday morning, got up, made the bed, showered, shaved, and put on panties and a bra. After applying makeup, wig, and stud earrings, I chose my A-line dress with elbow sleeves, white with blue chest pockets, shoulders, and belt, and a pair of white sandals.

Roger was in the kitchen sipping coffee and reading the paper.

I poured a cup of coffee, gave Roger a hug and soft kiss, and we clicked mugs.

While I was reading the comics, Lisa came out in a red sleeveless sweater that hugged her magnificent curves, with white shorts and sandals.

Lisa gave Roger a big hug and kiss, then came to me with the same.

Roger prepared breakfast. Lisa and I cleaned up the kitchen.

There were some football games on the TV in the background. Around three o'clock, Lisa and I decided it was time to start getting ready for dinner. We left Roger watching TV and went to change.

I stripped, scrubbed off my makeup, showered, shaved, and re-applied makeup. Zipped up my basque with garters, rolled on stockings, and attached them. Then panties. I stepped into my dress, zipped up the back, slipped on my sandals, and fastened the buckles. I fluffed out my wig and finished with large hoop earrings. This is the outfit I wore a week ago when I introduced Roger and Lisa to Dawn.

Chapter Eighteen: Out to Dinner
Saturday, September 18, 2004

Lisa and I went into the kitchen at about the same time. She was wearing a blue sheath that accentuated her ample bosom.

I brought up the Uber app on my phone, entered our current location and our desired destination, and waited for a driver to bid. Once we had a good option, I confirmed - the estimated time to pick up was five minutes. We went outside and waited for the driver to arrive.

A car came around the corner, stopped in front of the house and we climbed into the back seat and confirmed that we wished to go to Ruth’s Chris in the Tech Center. About twenty minutes later, we arrived, went inside to the hostess, gave my name, and were immediately seated at a booth.

A waiter came to the table, introduced himself as Dave, and asked if we’d like a cocktail before dinner. We all ordered vodka Martinis, and he went to the bar. A few moments later, he returned with our drinks and began to tell us about the specials for the evening. We asked him to come back after we had a chance to enjoy our cocktails. Dave went away.

We clicked glasses and sipped.

Dave returned to the table and asked if we were ready to order.

We asked if he could take a group picture. He suggested that we stand over by a planter. We posed, and he took three pictures using Roger’s phone.

We then selected something from the menu. Knowing I couldn’t take a doggie bag, I chose a smaller entree, a petite filet with baked potato, house salad, and a glass of Cabernet Sauvignon. Waiting for dinner, we sipped our Martinis, enjoying each other's company.

Dave returned with our salads. Roger and Lisa ordered Martini refills. We ate our salad, and Dave returned with our entrees, the Martini refills, and my wine. The dinner was fantastic.

As we were completing dinner, I brought up the Uber app and ordered a return driver. Dave brought our bill. I gave my credit card, and he went to process the charge.

Moments later, Dave returned and asked to see my ID, as was requested on the back of my credit card. I showed him my driver's license and he commented that I looked much prettier than my ID!

We all laughed.

I added a generous tip, signed and we departed - the Uber driver was waiting at the entrance. We returned home. It was only about eight o'clock.

Chapter Nineteen: After Dinner Drinks
Saturday, September 18, 2004

Lisa sat next to me on the loveseat: "Would you like to repeat our adventures of last evening?" I smiled and kissed her.

We had been naked together last night, there was no reason to be modest. I unbuckled my sandals and kicked them away. Unzipped and stepped out of my dress, draping it over the back of a chair. I unclipped and removed my stockings, unzipped my basque, and removed my panties. I was standing there naked and aroused.

Lisa watched me, then stood, kicked off her sandals, peeled off her dress, and removed her bra and panties, "Here I am, pleasure me!"

Roger was enjoying the show. He kicked off his shoes and socks, removed his shirt, stood, dropped his slacks, and removed his briefs: "Your choice, Miss Dawn!"

We were all naked. Roger and I were aroused, with hard-ons. I knelt in front of Roger, took him in my mouth, and proceeded to satisfy him. After a few moments, he convulsed and exploded into my mouth. This time, I was able to contain all his cum without any dribbling out onto my chin.

Once again, the statement from Diana that I would be swallowing cum came to mind. Her prophecy had come true.

I went to Lisa reclining on the love seat and dove into her pussy and began tickling her to multiple orgasms. She moaned and squirmed and began to buck and thrust, finally pushing me back and rolling away.

Roger picked me up and bent me over the back of the love seat, penetrated me, and began thrusting. After a few moments, he exploded and gushed into me, causing my knees to buckle. He withdrew, and I held onto the loveseat until I could stand.

Lisa motioned for me to sit on a recliner. She knelt and took me into her mouth, pumping me until I finally convulsed. She took my entire load, came up, and gave me a deep kiss, feeding me my cum. I swallowed and kissed her.

We all sat back, naked, and sipped our drinks.

"This has been one of the most enjoyable sexual experiences in my lifetime. There’s no way I could have fantasized about this in my wildest dreams. Realize that just three weeks ago, I was just a closet cross-dresser. I’d never been out of my house while dressed. I’d never had any interaction with anyone while dressed. I’d never had sex with a woman or a man while dressed. All of these events have happened in the last twenty-one days! I don't know about you two, but I’m exhausted."

“We’d love for you to come back and join us for one of our swinging parties. Mark and Nancy will be there. You will also meet Wanda and Laura, who didn’t come to the party last weekend. If Diana could join us, that would be wonderful,” Added Roger.

“Oh, HELL YES! Let me know when, and I will try to return.”

We finished our drinks, hugged and kissed each other, gathered our clothing, and retired for the evening.

In the bathroom, the face looking back was not very pretty. Lip gloss and makeup smeared unbelievably. After cleaning my face, I brushed my teeth, removed my earrings and wig, put on a cream baby-doll nightie, and went to bed.

Chapter Twenty: Time to Return Home
Sunday, September 19, 2004

Waking Sunday morning, I knew it was time to put Dawn away and return home. For ten days, she had been on cloud nine. Introducing her to Roger and Lisa, what a fabulous time! Meeting and enjoying Diana was fantastic. We’re going to meet up again. Being introduced to sex as a woman was exhilarating, and it will happen again.

I got up, stripped the bedding, and removed my nightie, G-string, and breast forms. Showered, shaved, and put on nude lace panties because some things never change! Used nail polish remover to clean my fingers and toes, so no shimmering pink remains. A golf shirt, shorts, and dock shoes - much easier to get through airport security! Packed everything, and put my suitcases and computer bag near the front door.

Roger was already in the kitchen, frying bacon and pancakes.

I hugged him. "This has been a whirlwind experience. Thank you for your hospitality and especially your acceptance of Dawn."

Lisa came out in a form-fitting powder pink blouse, white shorts, and sandals. She hugged and kissed me. “You look very different than Dawn. She’s much prettier.”

“And Dan has no hair, boobs, or makeup!” Added Roger.

After breakfast, it was time to leave. We loaded my luggage and computer bag, hugged, kissed, and said goodbye. I returned my rental car, took the shuttle to the terminal, checked my luggage, went through security, and boarded my plane.

The flight was uneventful. I went to baggage claim, retrieved my bags, located my shuttle bus, and returned home. Then to the mailbox to retrieve a week's worth of mail.

I missed having a bosom. I stripped and put on breast forms and a blue baby doll nightie with a G-string.

Back into the kitchen for a healthy glass of Chianti.

I repainted my fingers and toes with shimmering pink nail polish. Once they dried, I unpacked everything and admired my new wardrobe of bras and panties, dresses, and shoes. There was no need for makeup, a wig, or earrings, so I refilled my glass of Chianti.

A text message to Diana was returned with a phone call.

"I miss you," I said.

"Where are you?" She asked.

"I’m back home, with a glass of Chianti and wearing my blue baby-doll nightie. Where and what are you doing?"

"Still in Aspen. I’ll leave on Wednesday, spend the night with Nancy and Mark, and return to McPherson on Thursday. I miss you and look forward to seeing Dawn again. I want us to be happy together. And I can’t wait to have you between my legs again!”

"Hugs and kisses. Travel safe. See you Friday."

We hung up, I finished my wine and called it a night.

***** The Saga Continues - Dawn Visits Kansas will be coming soon! *****