A Trip South

By Happy Gilmore

Published on Jan 1, 2017

Transgender

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Christmas day is always exciting around our house. The wife's family comes over and this year was no different for there were 4 kids under the ages of 7. All believe in Santa Claus and all got spoiled by uncle Gil and aunt Laura. We spent the day entertaining and marvel at the kids' expressions but secretly I couldn't wait for all the in-laws to leave. Later on Christmas day they did. When we finally had a chance to relax, put our feet up and drink some wine Laura announced that she had a few gifts for Mary and I should got get her. I went to the extra bedroom and changed as I always would. It was late at night so I put red demi bra and matching panties and put on silk pajamas over top. When I got back Laura was happy to see me and said "Merry Christmas Mary' and here are a few gifts for you".

It wasn't just a few there were many.

"Thank you" and I blushed.

"Go ahead and open them Mary. I have chosen them for I think they will look brilliant on you".

She carefully handed me one package after another. The first package was a small and contained set of diamond earrings and necklace. Nothing extraneous but very nice. The second package contained a dark blue demi bra and matching bikini panties. I loved the color instantly and since she knew what I like to wear there was no doubt that they would fit. Next came a knee length black skirt that would swish each of my steps. The final package contained a white blouse with a bow at the neck. I liked each and every gift that she gave to me.

"Thank you my dear for the lovely gifts. You know how much I like to wear lingerie and how much I like to wear dresses and skirts. The gifts are wonderful. I love you!"

We hugged and we kissed and sat back down to enjoy our wine. As we it became later and more wine we drank the sleepier we got. We had a busy day tomorrow for we are driving from our home in Maryland to North Carolina to spend a few days with some close friends. I went to the bedroom first and changed my red bra to my sleep bra and put the pajama top back on. As I was laying in bed Laura came into change. I watched her undress and here profile was silhouetted with the light behind her. She took off her top and folded it and put them away, Took off her slacks and hung them up. Reached behind her and took off her bra and let her small breasts free. I love her breasts and wish I had some just like hers. She put on a white cotton night gown over her head and let it drop down her body. That light outlined her body perfectly and made me hungry for her.

The lights were off and into bed she climbed. She snuggled up behind me and reach around and grasped one of my budding tits in my bra. Tweaked my nipple and said good night. I am not sure how long we slept that way but it is one of my favorite ways.


We wanted to leave early and got up early, or at least early for a day off. We packed our things. I made sure to back the clothes she bought for me as well as two other bras, panties, stockings, ladies jeans, slacks, shoes, tops and accessories. We had a good 6 hour drive to our friends lived. That day I put on white bikinis panties, a white demi bra (which pushes and lifts chest into small boobs), and nylons. Over top I wore a pair of ladies jeans, and v neck sweater so that if a person was looking from the right angle they would see the little cleavage I had and maybe a glimpse of my bra. I felt the sweater and bra combination made my breasts prominent. Which I liked.

Once we crossed the border between Virginia and North Carolina we both needed to use the restroom so we stopped a roadside travel center. I know that North Carolina has anti transgender legislation but there was no way that i was going to use the men's restroom for with my hair, lipsticks, boobs and boots I looked more femme and male. I would be at risk to use restroom that the State legislative assembly wanted me to use for I am sure they would attack and rape me. We both went to the woman's restrooms, took stalls next to each other and heard each other discharge into the toilet. We both washed our hands, looked at each other and smiled for we knew that this right for both of us.

The trip was uneventful and we got our hotel just a sunlight was fading. Laura booked the room in advance and picked up the key cards and we made our way to the room. It was a lovely room with a large window facing west, a king sized bed, and sleeper sofa, a bathroom with two sinks and shower large enough for two or three people. We unpacked our things and in particular hung up our clothes that we needed for the next day.

Next was a search for food. We did not need something special and both went to an organic market for paninis and rolls. We grabbed a bottle of wine and headed back to our hotel.

We both changed into something more comfortable which really was the hotel robes, panties and bras. We slowly ate or food and drank our wine. Laura commented on how dry her skin was feeling so I willingly offered to rub her arms, legs and feet with lotion. She was like putty in my hands. When I sat directly across from her and rubbed her feet I could see the look of pure bliss on her face. I could also see a little wetness in her panties. I must have spent 20 minutes on each foot and when I was done she looked like she had an orgasm. After another glass of wine we both had work to do. Laura offered to do my toenails if I need hers. Well that was not a difficult thing for me to pass up on. First Laura removed dark red polish that already existing on my toenails for she wanted them to be brighter. Carefully she painted each one to a bright red shine. When she was done I did hers but in a playful pink. We admired our toes and giggled.

Tomorrow was the big day. We would see our friends again but not until late afternoon. There was still much to do but it was time to use that king size bed. We took off our robes and bras. I put my sleeping bra on and nightgown over my head. My wife put on the same nightgown that she wore the night before. We got into bed and this time i got behind her to spoon. My hand slipped to her breasts and softly rubbed and tweaked each.

She could feel the hardness in my panties against her buttocks and told me that there are only two women in this bed tonight "so put that thing away".

I moved my hips away from her kissed, her shoulder, and grasped her breast softly and then said "I love you".

The next morning we slept late, if you call 8 am late, Laura went out to get us breakfast. I laid in bed pondering the day that was ahead of us. It was a no pants party with our good friends Jenny and Joe. Joe and I had similar interests and both loved to dress and we were both both bi. Laura and Jenny were also bi and were intimate together from their days in college. We were a good match with so many similarities which did not include the fact they we each like being with the other. Another couple was invited to the party that we did not know but Jenny said that they were cool and that we would like them for the guy also liked to dress.

Laura returned with two large cups of coffee, orange juice, bagels with cream cheese and a small bowl of fresh fruit. In the past 9 months Laura has gotten onto into eat healthy, organic and taking supplements to provide additional nutrients. She gave me the orange juice and two multi-vitamins. I could never figure out why I got 2 and she got only 1, but I felt that she knew what she was doing. But she did know what she was doing. I had changed. I lost 25 pounds, my clothes fit differently from losing the weight, but my hips seemed slightly larger and my waist smaller. My skin was softer, at least appeared to me that it was, my body hair was lighter, and I was sometimes moodier. The biggest difference was up top. My nipples were much more sensitive and they seemed to have enlarged in length and width. The areola was definitely larger and darker. Before it just a little larger than my man nipple but now it seems size of dollar coin, and it was darker. Could I be growing breasts? Could my lovely wife be feeding hormones with my morning orange juice? Before I used to have man tits which were non existent and could not fill an "A" cup bra. Now it seemed that a "B" cup was perfect. I got certain amount of enjoyment of what was on my chest and loved cupping them. My nipples had a direct connection to my manhood, or whatever was left of it.

After breakfast it was into the shower where I had a lot of work to do. I needed to re-apply the hair depilatory to my legs, chest, arms, butt and shave my stubble. I have always had fine hair and not much of a beard anyway, but the depilatory works wonders. Once it was all on it was into a hot shower to wash it off and then to touch up with a razor.

As i was showering Laura joined me in the extra large shower stall. She helped me with places that I could not reach and trimmed around my balls and nut sac. I shaved her legs and removed all of her pubic hair. She knows I love that look. In the shower was washing her back and butt when she leaned over. I knew this meant. She was bent over at the waist and i went down to kiss her cheeks and started licking between the cheeks of her ass. I love rimming my wife's pretty ass for it gets her so excited. After 20 minutes of eating her ass she buckled forward. I rubbed fingers over freshly exposed inner and outer lips and then putting one, two and three fingers in her she came. She came with my fingers in her and my tongue on her ass. It was one of the best. The warm water was still crashing down on us.

"Stand up" she said.

As I stood she moved in and grabbed my breasts. "I love how these look on you. I know you like them too. See how sensitive your nipples have become and see how big your areolas are now. They are just like mine."

When she finished saying that she lowered her head to my left nipples and started sucking. I moaned with approval. Then she moved to the other. I was so turned on as she moved down and put my hard cock in her mouth. She is so good at sucking and brought me to the edge at least 3 times before she stopped.

"Let's get out of shower".

Once dry it was time to get dressed. I put on the blue panties and demi bra that she gave me for Christmas and white stockings. Overtop I put a robe on for now. Laura had me sit and by the window and then put on my makeup. When she was down she had me turn to the window where I was able to admire her handiwork. I looked great. It was time to finish dressing so I put the new skirt and blouse on, the new earrings and my black pumps. Next was my brown haired wig and the final touch was lipstick. Laura was dressed in a red dress, black belt, white stockings, black pumps. Her lingerie was red to match the season.

We stood together before the room mirror and smiled looked at each other and confirmed our love for each other. There we stood, two pretty women, very much in love.

It was time to check out and go to Jenny and Joe's. After a short 30 minute ride we arrived. At the door I was very nervous. Jenny opened the door and behind her was Joe, or should I say Josie, was there. Jenny had on red plaid skirt with white sleeveless blouse. Her shoes were red and stockings white. The makeup was exact. Josie had on mid-length black dress accessorized with a red belt around her waist. Her hair was past her shoulders and in a ponytail. It looked real. We looked at each smiled and complimented each other on how well all looked. We took our bags to our room for the night and returned to the living room to sip wine and catch up on the past few months.

At one time Jenny and Laura were in the kitchen and Josie and I started talking. We both expressed our extreme happiness on what was happening. Josie told me that she on had been on hormone for 15 months now and was having trouble hiding his femininity at work. He spent most of his days dressed as woman. I told him of my changes. The women returned but as they did we realized that both Josie and I needed a refill on our drinks so we went into the kitchen. I followed Josie and watched her ass shake as she walked. It was impressive. In the kitchen as she was pouring me some wine I came up behind her and caressed her ass.

Josie murmured and leaned back and said "that feels great".

My reply was "that does feel great and your ass is so femme looking". She turned and gave me a peck on the check. At that moment the doorbell rang.

It was Jeannette and Will, or should I say Jeannette and Wilma. Jeannette was tiny about 5'2" with large breasts that peaked out of her red top. She had on black skirt. Wilma had long blonde hair, brown dress with a black belt. Her lips were red and fingernails matched. The introductions were pleasant and there was so much in common. Joe and Jenny had known Jeannette and for a few months and expressed common desires.

It was time for dinner and it was lovely. I don't know when Joe and Jenny found the time to make it but was good, but that wasn't the primary reason that we drove 6 hours. In the parlour Josie and I had to be alone again. I rubbed her ass and we kissed. Wilma joined us. We started kissing each other with me in the middle. The real women all went upstairs the master bedroom where I they took turns pleasuring each other.

Josie was looking so very feminine. Her breasts were now a C cup and were more than a handful. We helped each other take our dresses, blouses and skirts off. There we were, the three of us in our bras, panties and stockings. I wanted to feel Josie breasts and as i did Wilma was caressing my ass through my panties. Josie and i kissed as i raised undid the clasp of front hooking bra to release her wonderful breasts. She cupped mine as as well. Wilma continue to caress my butt. Wilma stood up and undid my bra to release my b cupped breasts. Josie and I rubbed our new found breasts together. Wilma kissed my neck. I reached down to feel Josie between her legs and she was soft. She whispered that the hormones stopped her from getting hard. They had not stopped me yet and i could feel Wilma rubbing against my ass.

We released our hold and turned to finish undressing Wilma. Off came her bra and the molds fell out. It was clear that Wilma was flat chested but it didn't matter. We both got on our knees to lower Wilma's panties. Once they were down a large monster was released. It was at least 8 inches long. It was something Josie and I could share and share we did. We took turns putting that hardness in our mouths, or we would run lips up and down the sides of it. Wilma was very excited and we knew it would be a gusher soon. And gush it did into my mouth and into Josie's. I kept some in my mouth and kissed Wilma so she could taste her own cum.

Josie felt my hardness and told me to fill her up. She got onto her hands and knees and told me to take her. With a little split, and saliva from Wilma i was able to sink my 7 inches into Josie. She was so tight and such a great fuck. I pulled out and told her to get on her back, raised her legs up and entered her again. Josie moaned with joy. I moaned with passion and unloaded deep in her. Then I collapsed on her. Wilma came to us and we all kissed. Josie said she had an orgasm as i was fucking her.

Slowly will stilled our way upstairs to the master bedroom. The three women were in various stages of undress as we silently peeked in. My wife Laura's face was buried in Jeannette's pussy and Jenny was sitting on Jeanette's face and pulling on her nipples at the same time. Jeannette orgasmed with Laura's tongue in her pussy and Jenny orgasmed from rubbing herself on Jenny's face. They all collapsed and they saw us. Jenny told us to come and join them. Wilma and Josie joined Laura and Jenny on the bed. Jeannette and I went to a different room. Ten minutes later Jenny showed up in the room and she had a strapon attached her midsection. I wasn't sure if was for me or if was for Jeanette, but regardless I wanted her to fuck me. She fucked me good. She must have had a lot of practice from doing Josie, because she was almost as a good as man. She had the hip motions down. I shot a load into the Jeanette's hand and then she fed me my cum, which i gladly licked from her fingers.

Jeannette and Wilma had to leave before the evening was over so we all quickly put something on to say good bye. I put my blue panties and bra on and the others Laura, Josie and Jenny all put their bras and panties on as well. Good night Jeannette and Wilma hope to see you soon.

Laura and I went our bedroom and reapplied our lipstick and then rejoined Josie and Jenny in the family room. The fireplace was roaring and it was comfortable sitting there in just lingerie, however, i think Josie and I had the most protruding nipples. Laura and Jenny we discussing our changes and how pleased they were with the progress. Honestly, I was pleased too.

Laura and Jenny got up and changed places and Jenny was next to me and Laura next to Josie. Jenny started kissing me and Laura doing the same to Josie.

Jenny grabbed my breasts and squeezed them and whispered "they feel lovely".

Then she pinched my nipples "do you like that?"

All i could was moan.

Jenny proceed to lift my bra over my breasts and caressed them extensively. She licked and sucked my nipples which as you know drives me crazy. I loved that so much. She was getting me hard in my panties. Jenny leaned over "As you know Joe can no longer get hard so I want you to fuck me". I looked over to Laura and saw her sucking Josie soft little penie and could not get a rise out of it. Jenny pushed my panties aside and guided my hard cock into her. There was an enormous gasp from Jenny as I entered. She lifted her legs up and I got deeper and softly moved in and out of her. She was moaning and climaxed on my hard cock. I lowered her legs turned her onto her hands and knees. I wanted her rosebud.

Jenny felt me against that opening and said "not today Mary".

I pushed forward.

As the my head penetrated Jenny wanted me in deeper, all the way in and hold it there. Which I did. She was moaning. As I was fucking Jenny in the ass I looked over to Laura. Laura was doing Josie in the ass. Our eyes met and we watch each other fuck. It was a sight to behold.

The next morning after we all showered to get the previous evening's funk off of us, and to have breakfast the four of us put on our bikinis and jumped into the hot tub for a soak. It gave us a chance to show off our swimsuits and I was able to truly admire the Joe's hairlessness and his budding breasts, though his were larger than mine. Jenny asked if he should have implants. Both Laura and I said no but Joe did. So maybe next time we see them they will be larger.

Laura and I needed to hit the road soon so we returned to our room and got changed. I put on a black seamless bra and high cut panties. Over top I work a sweater, jeans and boots. Laura was wearing a white bra and beige panties with also sweater, jeans and boots. After we were dressed and packed we said our goodbyes to Jenny and Josie. Josie and I had a nice open mouthed kissed. Laura and Jenny did the same.

The trip seemed long but we both enjoyed our time to Jenny and Joe and Jeanette and William were a welcomed addition to our fun. Laura asked if I wanted to do it again and I said yes. Oh and she did finally admit that she was feeding me hormones and liked the changes that had occurred. As did I.

As we got close to home, she asked "Do you want to be femme full time?"

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