Dating While Savannah

Although I dated when I was younger, this was a scary start for me. I went to Craigslist and posted that I was a passable transgender woman seeking men for dating. For some reason, I never read any of the other posts. I guess being raised in the conservative South and being a Baptist church goer had made me quite naïve.

I dressed nicely as Savannah and went to a professional photographer and had some pictures taken. I posted them online and sent them to my Mother and Sister.

What I found was that many men on this site were merely horrible jerks! Or, as I later found out, they were called Trolls. They only want sex! The disgusting standard replies I received were, “Do you still have a dick?” “Have you had the operation?” “Do you take it up the ass?” “I’m married; I have to be very discreet,” “Do you have real tits?” “Can you send me photos of your tits?” “Do you swallow?” “I can’t be seen in public with someone like you, or I can’t have someone like you to come to my place.” “Can you dress slutty for me?” These men (I use the word men lightly) were indeed not gentlemen) but entirely self-serving creatures. I felt more like a novelty item rather than a woman.

I was horrified and kept asking myself where all the kind and gracious Southern gentlemen were. I also looked at a few internet dating sites. I said I was a real woman, other sites that I was a transgender on some of them. I got a few dates from both and had a lot of fun. At the latter websites, I ran into some of the same questions as above. One site kicked me off for not being a genetic woman. I never spent the night with anyone. I met a handful of nice men, but seldom any of what I experienced in the South. I stayed on the sites for less than six-months and went out on about five dates. Never a second date. My choice because of their manners, or lack thereof. I enjoyed the nightclubs the best.

I was walking back to my car in the parking lot or garage from the nightclub one Saturday night when I realized how vulnerable I was. I felt how genetic women might feel when walking alone at night. And being a transgender woman, I had read sad stories where transgender women were beaten up or killed. I was no longer dating back in my sleepy little town to chaperoned socials or dances in the small community where everyone knew each other or their families. I decided to carry a whistle, pepper spray, and a small handheld personal taser. I even took a self-defense course for women offered by the local police department. After dark, I walked around my car before getting in it and walked with my keys and whistle or pepper spray in my hand.

As Savannah on weekends, I found myself going to the theater, concerts, museums, art galleries, and nice restaurants where I met a few well-dressed gentlemen to date. If I saw a ring on their finger, I walked away. I would tell them I was not a real girl, but few seemed to believe me. Many walked away, which was fine with me since I did not want to hurt or deceive them. Dating on weekends was much easier since I had more time to get ready. But if someone wanted to have dinner or a movie on a work night, it pinched my schedule to prepare after coming home from work—movies are more casual and more relaxed to get ready for.

I told Mother what I was doing. She said, “To be a good girl and don’t tease those poor men too much.” She would call and ask about my dates and how Savannah was doing. She never asked about my work.

It was early March, and I phoned Sis and told her I would like to come home on Mother’s Day and surprise Mom and asked her to reserve a table at a nice restaurant, and brunch was on me. I would be flying as Savannah and ask if she could pick me up at the airport the day before. But if she couldn’t, I would gladly get a cab to my hotel.

Two days before Mother’s Day, I was at the baggage claim and looked around for Gwen. I flew in jeans, sneakers, and a loose button-down chambray blouse that was buttoned half-way down, showing a white tank-top under it. I saw Gwen first. Then Gwen’s opened wide. “Savannah!”  We jumped up and down hugging each other.

“Savannah! You look amazing. I missed you. Everyone misses you.” 

She drove me to the Hilton, where I had booked for one night, so I could dress to meet them tomorrow.

“What time and where are the brunch reservations?” Sis stayed joined me for dinner in the hotel, and we caught up on a lot of things. Then I noticed a ring on her finger as she reached for some bread. I pointed to it.

“Are you…?”  I wondered how could she not tell me earlier? She would not let me finish my thought. She started smiling and began telling me the whole story about Steve, how and where they met and their plans, and of course, her ring. We stayed until they kicked us out of the restaurant. So we headed to the bar for another hour or so. She could not stop talking, and I could hardly get a word in.

She finally stopped talking and reached over held my hand. “I’ve spoken to Mom and told her that I want Savannah, my beautiful Sister, to be my Maid of Honor. I cannot think of anyone I would rather have. Will you? Please? You know I won’t take no for an answer.”

It dawned on me what she just asked. I was breathless. My left hand was on my heart. I finally smiled and opened my eyes wide.

“I’d be delighted, Sis. When is the date? I wouldn’t miss this for the World!” Then I proceeded to wipe off a tear as not to smudge my mascara. Gwen jumped up with joy and knocked over her chair, and both our drinks spilled onto the floor.

“Thank you, Savannah. I mean, Sis. You, being my Maid of Honor, means the World to me.”  The bartender gave free drinks for the drinks we (Sis) spilled. Sis made me feel fantastic. I recalled when she yelled out, ‘I love you, Sis’ when I went out with Fred to the ball.

Mother’s Day morning, I ordered a light breakfast in my room since the hotel was also getting ready for Mother’s Day Brunch. I chose a pale-yellow floral-print long-sleeve spring wrap dress that was just above my knee and beige pumps. I checked out of my room and asked the bellman to get me a cab and gave him a couple of dollars for putting my bags in the trunk of the taxi.

After arriving at the restaurant, they were so kind and accommodating to me by putting my bags someplace safe. I looked around, saw Mother had her back to me, and Gwen was talking to her. I walked and stood behind Mother and put my hand on her shoulder, and asked if they minded if I could join them for brunch. Mother turned and looked up at me. She paused, then looked at me again, then quickly stood up and kissed and hugged me as she has never hugged me before. I brought her flowers from the hotel’s gift shop and gave her the Mother’s Day card signed, ‘Happy Mother’s Day to the best mother anyone could ever wish for. Love you, Savannah .’ During brunch, we talked and chatted as I had never left.

Mom turned to Gwen and asked, “Did you know she was coming?”  She replied yes and told her about picking me up and us having dinner last night.

During brunch, I looked around and saw Mrs. Atherton, her husband, and Donna at another table on the back-left side of the dining room. I excused myself and when over to talk to her.

“Happy Mother’s Day, Mrs. Atherton.”  She turned and looked surprised to see me. Donna jumped up first, and we hugged.

“Savannah. Look at you. You’re a grown woman now.”   

“Mrs. Atherton, you know you will always be one of my mom’s too.” I kissed her on her cheek.

“How long are you in town?”

“I leave Thursday. “

“Will you, me, Donna, and your Mother and Sister if she wants to have lunch one day?”

“Of course, it sounds fun. I’ll ask Mom and Gwen?”  Did I say Mom and not Mrs. Thomas? I was supposed to be from Atlanta.

“Does Wednesday sound good? I have pictures of the ball you’ve never seen.” I never answered her about Wednesday.

“Really! Are there more? I already can’t wait to see them,” I said with a big smile. I will call you tomorrow. Enjoy your special day, Mom.”  After brunch, I collected my bags, and we drove home and continued talking until one in the morning. I called my old girlfriends the next day, and some of us got together for dinner on Tuesday. That was so much fun. We talked about dating and boyfriends and our future dreams. It was so lovely to see them, to be home with people who remembered and accepted me as Savannah.

Mother appeared enthralled with the skin on my face.

“How do you keep it so youthful, Savannah ?”

“My two best mentors taught me well. Ever since I became Savannah, I cleanse, exfoliate, and moisturize my face and skin every night, just how you two showed me. And to wear sunscreen every day.”  Mother and Sis were in awe.

“Savannah, your skin is so smooth and radiant. It is unbelievable.” Sis reached and ran her fingertips over my face with her fingers. “Any cosmetic company would love to get a hold of your skin for commercials.”

Mom said. “Keep it up, and you’ll be on the cover of Cosmopolitan magazine.” 

“I have to thank you two for everything and all I’ve become and transformed into.”

When Mother stepped away for a minute, Sis joked and asked if I have given anymore blow jobs. Of course, I said, “No.” I was truthful. The only one, and that was with Fred. (Very fond memories and images flashed through my mind. How big and hard. The texture of his penis, its warmth, and the only way to describe it – the unique taste of his ejaculation. I will never forget that day or the ball. I regained my senses and composure when Mom returned.)

I told them about some of the dates and places I had been on dates. A restaurant named Pier 71, that my date took me to has an excellent policy. I asked the waiter where the ladies’ room was. Surprisingly, he said, “I’ll show you. The waiter offered his arm and escorted me until I could see the sign.”  What a sweet gesture. When I returned, my date told me that one of the servers said he was very brave, allowing me out of his sight. I found that so cute. During dinner, I saw many other ladies being escorted by the waiters. Excellent policy, I thought. Sis and Mother said she had never seen that before but liked it instead of someone pointing them in a vague direction.

I loved being home with Mother and Sis. We talked about Gwen getting married and asks what I could do to help. My head was spinning, thinking about being a Maid of Honor.

I returned to the windy city refreshed and happy that I could see Mother, Gwen, and girlfriends and spend time with them. I missed my girlfriends a lot but relished the ball and the country club in a special way. I was proud to now being accepted as a woman and not a young girl.

As for dating, many older men needed someone hanging on their arms at big events or parties. I went shopping for a few slinky cocktail dresses, new classy strappy heels, and some cute little handbags. I loved every second of every minute of it, my time being Savannah. I loved the black-tie events. All the men looked great in their tuxedos, and the ladies were gorgeous in their cocktail dresses or long gowns. I checked out the ladies and knew that they were checking me out. On rare occasions, some men would have too much to drink and tried getting frisky with their hands, but I seemed to handle it and put them in their place.

The cocktail dresses posed a significant problem with my non-existent breasts. I could no longer insert breast forms, especially in the backless dresses. I found this new self-adhesive breast form called NuBra that did not require tape adhesives. And best of all, they were reusable. I was glad I did not have to buy new bras.

Along with the makeup tricks Mother had shown me, the new breast forms, and the NuBra, the tricks worked. I purchased two pairs of the NuBra from Sally, my saleslady at Nordstrom’s. With this product and what Mom showed me I now had breasts.

My work was rewarding. But being Savannah was fantastic.

The relentless lingering thought returned. I wanted to be Savannah full-time.

Gwen’s wedding was coming up.

Next: Wedding dinner and bachelorette party.

Tags: featured, fiction, Transgender

Category: Fiction