Eloise’s Journey


This is a fictional story. It is written from Eloise’s viewpoint in first person.



Hello all!! This is Eloise Schmidt.

I haven’t always been Eloise. I was named Brian at my birth. But by age 4, I found I liked to play with my Barbie dolls and wear Wonder Women underwear. I had an older sister (Emma) who loved to have me join her at tea parties and we loved the Disney Princesses.

Fast forward to middle school and sixth grade. I felt awkward in gym class as we changed into athletic wear and then shower in a group afterwards. I tried to get to gym class early to quickly strip and change into my gym clothes and then was slow coming back to the locker room after gym class so to shower without others watching me. I was frequently late to the next class, and had to stay after school a few times for being tardy to my geography class.

I don’t know what happened, but for Christmas one year, my Mom asked ‘What do you want for Christmas Brian?”.

My answer was “Girly Panties”. She said “No, that isn’t appropriate”.

My reply is “Why not? I like dressing like a girl. And maybe some blouses, makeup kit, and shoes”.

So, I got girly clothes and things including ten pairs of pretty pink and pastel panties, two nighties, three blouses to wear at home, the makeup kit and my first ever female shoes for my Christmas. I wore those shoes until they fell apart. From that Christmas on, I have only worn girl / woman underwear / panties. My sister Emma and my Mom helped me with the make-up. TGIF – thank God it’s Friday had a special meaning for me. For Friday night, and most Saturdays and Sundays Eloise came out, and Brian went away.

Mom worked it out with Dad – and the two of them were really understanding. By eighth grade, my hair was long and at home on the weekends, I practiced putting it into different style. When Emma started having periods, I had ‘pretend periods’ and wore a pad in my panties.

By ninth grade, I really was identified as ‘transgender’. I was a male and I ran cross country on the boys team, but in the locker room, I was the ‘girl’ among boys. One day after cross country practice one day, a new kid on the team started to tease me about my pink panties. Mike Ragner, the captain of the team, pulled the new kid over and in very certain terms told him that I was part of the team and that he could like it – or he could quit the team. From that day forward I was ‘protected’ by the team.

Every year I became more feminine. There were some days that I even wore dresses and put my long hair in a girly style. By senior year, when the topic of going off to college came up, I insisted that I was going off to college totally as a female.


My parents and I had ‘the talk’ about transitioning. I had done my homework and understood the process. I would have to get rid of any facial and body hair (and had actually started on this during my senior year with electrolysis). There would be hormones to take, and feminine voice to improve. I was ready. My gender therapist had approved me as a transgender, and I started taking female hormones three weeks before the end of my senior year. To honor my cross country friends, I graduated in ‘boy mode’. That was one of the last times for ‘boy mode’.

I turned 18 in October.

My mom wanted me to know more about female’s bodies. She had walked with me into her bedroom (with my dad’s permission) and stripped to her bra and panties, and then asked me to take off her bra. I was truly in awe of her breasts. Believe it or not, I actually cried out of desire for real breasts just like hers. They were so full, and the nipples were erect as I took off her bra. (Bras were not new to me, as I had worn bras off and on for several years.). She circled her nipples with her fingers and then asked me to do the same. She then asked me to kiss her nipples. I tingled with excitement.

She then had me take off her panties. She wore some very sexy panties from Victoria’s Secret I think. She then sat on the edge of the bed with her legs spread out while I looked at her vulva (or as she called it, her pussy). She talked of love, of procreation (that is, the birds and the bees, and of my father fucking her and making Emma and myself). She also talked of female lovers and of ‘eating pussy’ and said that one day I could experience that. [I wasn’t sure, but looking back on this experience, I think there must have been times when Mom enjoyed another woman’s sexual company – and possibly as a three-some with Dad.]

I watched her as she fingered her outer labia lips, circling them gently. She moaned and increased the pressure as I watched. She squeezed one of her breasts while she fingered herself (or, if you will, while she masturbated in front of me). It was very sensual and her motions got faster and faster until she moans and sobbed and reached a climax. I was aroused just watching her. What was maybe the best part of the experience was that when she had reached her orgasm, she had two fingers in her vagina and held them out to me and said “lick samsun escort my fingers”.

I had tasted my cum as a male after masturbating and didn’t like the taste all all. But the juices on her fingers were delicious.

She pulled up her panties and said “Someday Eloise, this will be your experience as a woman. You’ll get to taste or ‘eat’ your girlfriend and she will get to taste or ‘eat’ your pussy juices” She paused and added “I think being a female is a million times better than being a male. I am so excited to be your mother as you go on this journey”.

We hugged after she exposed herself to me.

I never again saw her pussy in that manner again, although she did ‘flash’ her breasts a few times to me in a playful manner.

Dad was a partner in a Big Four Accounting company and that company had a very liberal insurance policy. Most of my transition was going to be covered by insurance (which was important as full transitioning can be expensive).

I had chosen Central State University for college with my parents help. My mom and I had kidded early on that I should join a sorority, but as the summer went on and the hormones kicked in, joining a sorority seemed like a reasonable thing to do. My Mom had been a Delta Zeta, so my first leaning was that direction for a sorority.

Central State allowed first semester freshmen to rush Greek organizations, but could not move into sorority houses until second semester (if space was available). I was on campus a week early for rush and for fall orientation. I visited the Tri-Delt sorority (Delta Delta Delta); Alpha Chi Omega, Kappa Delta and Delta Zeta. All of the sororities knew I was transgender. Alpha Chi Omega was already known as transgender friendly. I talked with the advisor for Delta Zeta who called their National Organization and got the green light to have a transgender woman as a member. There were two local sororities that accepted only lesbian members. Tri-Delt did not have a policy and they seemed to be confused about having transgender women in their sorority house. In the end, I was considered a ‘legacy’ member at Delta Zeta since my mother had been a Delta Zeta, and they extended a bid to me, and I selected them.

Also in this first week before classes started, I made a point of finding all and talking to all my professors. I didn’t want them deadnaming me the first day or class (or ever) by calling the roll looking for Brian Schmidt, not Eloise Schmidt. Yes, my legal name was still Brian, but I was burying that name one day at a time (and one hormone pill at a time). Some faculty were very supportive. I had James Tuttle as my Principles of MacroEconomics professor and he seemed very cold to having a transgender women in his class. While not wanting to judge him, in his office he had pictures of his family – outside of what I thought was a conservative church – with the women in long dresses and the boys in black pants and white shirts.

I did move into a standard dormitory for women. The campus housing staff had done their best to accommodate me. I’m not sure if it was intentional (I thought it was), but campus housing assigned Tamara Perez as my roommate. Tamara was an avowed lesbian. It was a good match.


During the first week of classes, the many campus organizations had an ‘activity fair’ and you could join any of it seemed like a hundred groups (or more) from chess club, to marketing club, accounting club, university singers, and for Tamara and myself the LGBTQ society. There were four male-to-female (MTF) transgender women in that LGBTQ Society and one going from female to male. Two of the four MTF were seniors, two were juniors and I was the new transgender female and a freshman. One of the seniors was very special to me as she had undergone her vaginoplasty surgery over the summer and was truly female. One of the junior transgender women was still pretty much in the closet and only open at our meetings.

Tamara was also very happy to be associated with fellow lesbian students on campus.

I’d like to add a comment. Some people have the mistaken concept that transgender people are very active sexually. To me (and for most of the transgender women that I have met), that is NOT the case. We are like a fish out of water. We are not males (although we do have the male equipment; we are not yet females). I for one had ‘kind of’ decided that I never wanted a boyfriend and that when that day come, I’d be a lesbian woman. Other transgender women I knew were planning on being bi-sexual. I experienced a great anxiety called gender dysphoria – or the distress or angst from being a female in a man’s body. Even though I had a penis and even though at times I would masturbate to excite myself, I was really LONGING for that day when I had a vagina and the image in my head would match the reality of my body.


One night when Tamara and I were talking about gender issues, the topic of genitalia came up. Tamara really had never touched a penis and I had only looked at escort samsun my mother’s breasts or pussy once.

Tamara had never seen a penis before, so I pulled down my panties so she could see mine. It was already shriveling a little as the hormones were kicking up the estrogen levels in my body.

She asked “Can I touch it”?

I answered “Yes”.

She gingerly touched my penis, which with her touch had become a little erect.

I said “Watch out. I may reach a climax”.

She asked “Will that hurt you”?

I answered “No. Just rub me up and down a few times”.

Tamara was so enthralled to be touching my penis and was shocked and amazed a minute later when I came.

She asked “Is that normal”?

“Yes, I’m sorry”, I answered.

I quickly added “I hate my penis; I hate what it stands for; I hate being in a boy’s body. I want to be fully female.” I started to cry. I’m not quite sure why, but soon I was bawling for wanting to be a women.

Tamara came to me and said “Don’t cry Eloise. You are getting closer even day. Even I can see how the hormones are changing you. Don’t lose heart”.

I don’t know what happened, but our lips touched and then our tongues found each other in the kiss. It was the kiss of two lesbian girls sharing a dorm room. And … one of those lesbian girls wasn’t quite a girl yet.

We didn’t do anything more that night other than kiss and hug (okay, we did a little more as Tamara’s hands “strayed” over my breasts for a long minute and my hands ‘strayed’ over her breasts for a long minute as well).


It was two days later that Tamara and I had our first real sex. I wanted to love her as a female loves another female (that is, I guess as lesbians love).

We talked about how to excite her, how to do foreplay, how to approach her pubic area. I had read that women could have multiple orgasms and that was one of our goals for the night, as well as establishing a deep love between us.

It may have one of the best times of my young life. I excited my roommate / lover with kisses all over her body.

I kept asking “Do you like that?”

Things Tamara liked, I kept on doing; things she didn’t like, I didn’t do. After a fair amount of foreplay she begged me to suck her breasts. I had left her bra and panties on, and I unhooked her bra and truly fell in love with my girlfriend’s body. She was 18 (and I was 19), so her breasts were maybe still filling in, but they were perky and when I sucked her nipples they were standing at attention for me.

I sucked more and then suddenly she stiffened and her body shuddered.

“Wow, you just brought me to my first orgasm of the night”. Tamara whispered to me.

Not quite knowing what that meant (after all to me a climax was the be-all and end-all of my male existence). She pulled my hand to her panties and put my hand on the fabric between her legs. Her panties were soaking wet.

“Now kiss me”, Tamara requested and I did. The passion of our kiss was almost enough to get me off, and that was something I (and we) didn’t want until maybe the end of our activities. Her fingernails were digging into my butt through my pink Victoria’s Secret panties.

“Stop” I said “What is 37 times 43?”.

“What?” she asked.

“I need something to keep my brain occupied and keep me from reaching my climax too soon.” Was my reply.

“1591 I think, How about what are the prime factors of 144?” I asked myself.

That was enough of a distraction that I cooled down my ardor a little.

I was a complete amateur when it came to sex. I knew I wanted to excite Tamara. My mother had talked about ‘eatting pussy’. I slid down to her pubic area and slowly touched both sides of her outer vulva lips with my tongue.

Tamara responded with “YES. Continue that”.

I wanted to be sensitive and to give her pleasure. I had read about the clitorius, but wasn’t quite sure what to do to stimulate it. I put my tongue on that nobbin – and instantly she jumped and said “NO, that is too rough”.

I asked her “So, what would you like me to do?”.

She answered – “I’m not sure, but that was too rough – maybe use your tongue but not on that area and definitely not so hard.”

I thought it hadn’t been that ‘rough’, but I did back out and licked her vulva lips again. Then very carefully came up to the top of her pussy – but didn’t directly touch her clitorius . That seemed to work for her as she reached another climax.

I then took two fingers and gently circled her inner lips and into the vagina canal. Tamara agreed that was splendid and shortly after reached another climax.

Being naive, I asked “Do you want more?”.

Tamara laughed “Of course, I want more. That is pure pleasure, better than any drug. But, I guess for tonight I’ll be happy with my orgasms”.

She then turned to me. I didn’t know that I would get so excited when she sucked my breasts, but I did. Something deep inside me sighed – maybe it would be samsun escort bayan the start of a womanly orgasm in a couple of years. Then Tamara pulled my Victoria’s Secret panties down and just that action caused me to cum – unfortunately over her face and hands.

“Yuck”, she said upon tasting it. “How can some woman like that taste? Not for me!!”.

After we rested I asked her about her previous lesbian experiences.

I was totally amazed when she said “You are the first”.

I asked “How can you be a lesbian and never had experienced any female love making?”.

She replied “I just knew that I would like woman and not like men.”

I teased her “So, now you are a lesbian because a man excited you to several orgasms?”.

“Yes. But you are not a man. You are a loving, perfect female, but still stuck in your man body.”.


My first semester was a very good one. I aced Dr. Tuttle’s Principles of MacroEconomics class and he even asked me if I might want to do a joint professor / student paper on Bitcoin / Ethereum and Understanding and Acceptance of electronic money by college students. We did the paper during spring semester and it did get published in the Northeastern Journal of Macroeconomics and even won a prize as the best student / professor paper.

I was planning on being an accounting major like my father had been. I took Calculus for Business majors and got an A in that class. I also had Freshman Composition I, and that was my lowest class at a B plus; Management Information Systems (I loved the Excel spreadsheets, the database management and security modules) was an “A” ; and Business Communication was an “A” – so a 3.80 GPA for the first semester.

Every Tuesday night was Delta Zeta pledge night. We learned the history of Greek organizations on campus, and the history of Delta Zeta. Plus one a month, we had a social night with one of the fraternities on campus. That was always an interesting night as some of the guys wanted to hit on me to see what a transgender woman was like. I was pleasant, but said “no” everything. Of a good thing with Delta Zeta, I asked if Tamara, my lesbian roommate could be a late addition to the pledge class and because two girls had dropped out, my request was approved.

But, maybe the most fun and interesting was the LGBTQ group. We participated in the Hartford Pride March; helped with talks at various events about being queer on campus; and had a great social life. While I had 87 Delta Zeta ‘sisters’; I had four transgender ‘sisters’ and they were probably more important. By the end of fall semester, even our ‘closet’ sister was out to her parents and family and friends as a transgender woman and it had been nicely accepted.

Tamara and I were inducted into Delta Zeta at our first meeting in January. The campus required that students joining a sorority must have at least a 3.00 GPA, so had to wait until grades were reported. It was possible to move into the sorority house, but we opted to stay roommates in the dormitory. We also had discovered that we were the same size in clothes and even though we had some different preferences, we could swap outfits.

More importantly (at least to me) was that the Hormone Replacement Therapy was working. My breasts were real and I needed a “38B” bra. (I also did a lot of breast massage too). I worked on my feminine poise, walking like a woman, talking like a woman, walking in high heels, and more. I wasn’t just “passing” as a woman, I WAS a woman (with one exception that ugly between my legs).


Tamara and I were working out some sexual relationships. I was the first to start when we were intimate and generally I did a long foreplay on Tamara. We experimented with dildos, with anus penetration, and with a variety of positions on Tamara – generally leading to me ‘eating pussy’. We loved to shower together and had slid our two single beds together to make a double bed.

I needed to start by exciting Tamara, because if Tamara started and got me to an orgasm, that was it – it would be over.. (Men are so limited – only one orgasm; while Tamara could have several climaxes a night (or none)).

I loved when Tamara sucked my breasts. I also found that my toes were an erogenous zone and she could excite me by sucking them as well. Our kisses were so deep and sensuous. While partners, we also agreed, mostly for Tamara’s sake, that she could have real lesbian partners. She was missing out on so much by not having a true female for sexual escapades.

My spring semester grades were a 4.0 with Principles of Financial Accounting I; MicroEconomics, Quantitative Analysis, Freshman Composition II and my General Education Science course (where I took Biology 206: Human Sexuality). The professor for the biology course knew that I was transgender and I was frequently a role model for human sexuality – with a penis – but looked, thought and acted like a woman. Some of the weirdos in the class, both male and female tried to date me to see my private plumbing parts.


At the end of spring semester, Delta Zeta had its spring formal dinner dance. I took Tamara and Tamara took me. There were about five female / female couples at the event. Tamara had gotten a shimmering white strapless prom dress that really accented her breasts. She had three inch heels, and a tight ass. She looked like a million dollars.