Jenny’s Story – 1

Jenny’s Story – 1
The College Years – Book 1

By Jessica C

It was the late 1970’s, the fall of my junior year of college I hadn’t gone to the mixer at nearby Amber University, a women’s college and missed a funny event. The women challenged our guys to a contest; the resulting loss ended up with one of the guys dressed by the girls as another coed. He was none the worse for the experience as he enjoyed the attention and was surprised by how convincingly they got him look like a girl. While a few other students were jealous of the attention Hal received they did not volunteer to exchange places. Hal later told me of the fun he had with the women of Amber and his transformation to Halley. I secretly wished it had been me.


It is now weeks later when I’m in the group going to the dance at Amber University. I didn’t have to work like I usually do. I’m not one to worry very much about my studies especially on Friday night. The gals once again challenge the guys so we go over to a lounge at one of the dorms. Following Hal’s suggestions and not wanting to be too obvious I sit at a table watching some girls playing some card games. I not know it’s the contest site. The contest is even with a card game I usually play fairly well.

One of the girl’s handed me a deck and I quickly play a hand and win.

The challenge is to score over 200 points before one losing over 100 points. One can actually win in one game, while it takes a number of losses to lose the contest as they have set it. I’m selected to play but if we lose the Amber women get to select any guy of their choice. If we win the opposite will be true, with some restrictions either way and what can or cannot be done. That makes playing the game interesting for everyone.

While my thoughts aren’t jumping to anything bad, anyone of the gals would be a great prize in my eyes. I agree to play but I state, “I’m not wanting to be the one chosen.” The contest starts one game late as I’m just in the process of running the table again.

The next game I lose some points but the following game I made them and a few more back. But I mistakenly fail to win more points. It is either the third or fourth game when another gal, Anne arrives. I’m sure she would not be the choice of the guys leaning towards blondes, but she would be my choice to be the prize. She’s a big enough distraction that I miss the next opportunity to score big. Our score slips back into the negative yet I still feel confident that it will be easy to win.

I’m about to make a good score, when I drop some cards, losing the hand and a great opportunity to score more points. I’m now in danger of losing. I’m soon over the losing score, but am told I could push our luck to play back or throw it in now and concede. The guys urge me to try and play back. The Amber students say I risk a more severe discipline for the guy chosen if we lose by 140 points. I try and play and score some points back. But it will be over 140 points at the start, but it is rare not to score any points. I hadn’t done so yet.

Sure I can easily play back and win. I play two games have more than pressed our luck as even my own guys hassle and distract me. The guys did not I want me to play the last game. I make a poor play that makes for a rotten hand. I did not notice most of the guys have already jumped ship and gone back to the dance.

By pushing our luck and trying to play back, the guy chosen will now be staying the night maybe the weekend. That is unless Amber dorm officials find out what we’re doing. I’m selected. Anne sets the other gals into their transforming action, “It looks like your friends left you to pay the price of your poor play. But don’t worry you will see them again.”

I tell her, "I’m not sure I want to as I don't know what I will look like."


I’m given two paisr of panties to put on as they’re taking my clothes off. I remember Hal sharing about how they had him stripe down and helped him putting on his girl clothing. I feel goose bumps as the panties go up my legs. The girls are happy to find limited hair on my legs. They spread a cream on my legs and a few minutes later wipe them clean with a wet cloth. What little hair there was is now gone. They tease me, and have me feel how smooth and silky my bare legs are. They do feel real nice, though I do not say so.

One girl nibbles on the back and side of my neck from behind me, asking “Do you like it?” It gave me feelings that I’s unwilling to tell them about.

I say, “If I was expecting it and knew the person, I think it would feel even better.”

She responds, “You had a reasonable response for a normal girl.”

I bark back “I’m not a girl”. They help me put on a bra and they put two forms in the cups. I’m asked to sit as they ask me to put on a pair of pantyhose. I had earlier told them that I don’t have any sisters. So when I put them on without problems they share little things like that with Anne. They have me shave my underarms as well as my face. I put on a half-slip and then I wiggle into a mini-dress and feel like I’m already being transformed into a pretty girl. I did not expect to like it as much as I do.

Anne asks, “Please sit down again, we’re helping you with your make-up. Tonight, you’re more than an attractive college student.” It’s more than lipstick and the eye shadow that they apply as makeup. They use what they call a concealer for blemishes as well as a foundation.” The make-up is not heavy like I expect, but it does more than I could imagine. The girls are surprised as I am, by how well I’m being transformed into a college co-ed.

One girl asks, “When did we stop dressing a boy, she’s totally changed into a girl?” Anne pops her head in and smiles at seeing my appearance change. The last thing they ask about is a girl’s name. I suggest Jenny, someone says, “What do you think of Jessica Connors?”

I ask, “I don’t know who she is?”

Beth says, “You are Jessica for the remainder of your time here.”


Then they slip heels on my feet and help me practice dancing in them. I am very scared as we walk back to the mixer. I work hard to walk and dance like a girl not wanting to be found our by my friends from Upper Valley College.

While I do go to the dance for a short time, we’re not there very long. I hear two students from my college suspecting another person is in really me. She stays behind as we leave the dance.

We go to a pub off campus with dancing. A few guys ask to dance with three of us, and Anne obligates me to say yes or be found out. We dance with them and again later before it’s time to leave and go back to campus. Anne gives her guy a kiss. My dance partner gives me a kiss to which I respond. I am sure Anne made a note of it.

When we get back on campus and I am not sure what is to happen. I am certain the college dance is about over. I ask, “You had your fun and I’ve cooperated. How about allowing me to change and go back with my friends?”

Anne asks, “Did you forget how much you lost by; you’ve earned the privilege to stay overnight.”

A student who met us back at campus says, “Your friends have already forgotten you and have gone back to college. Or out with some girls.” We sit around and talk until I’m really tired. Rudely I’m told, “There are things a girl has to do in getting ready for bed, like take off makeup and moisturize one’s skin.”


The next day I’m awakened early, “You need to shower before the other girls?” She showers in the next shower room over. She says it is to make sure I do not spy on other students. Cyndi did not seem very inhibited as she is still drying herself the next time she checks on me.

I’m to dress more casually like other coeds. I do not notice how relaxed I am. They take me to breakfast and then to the admissions office and I’m given a tour of the campus as a perspective female student. I think their joking is a bit much. It surprises that school officials are either fooled or going along with things.

I am however impressed by how they approach education with such a high standard of academics, practical application of studies, encouragement and flexibility. I learn Anne is both an engineering student and basketball player. They have an exhibition game in afternoon that I’m to attend. First they have me doing my studies. Two of their students have business administration classes similar to mine. Having done some admissions exam I’m not interested in studying but that isn’t an option.

They have tested my eyes and within an hour I’m fitted and using needed glasses. Unfortunately I cannot take them back to my college as the fashion is definitely for a woman. With others reading and working with notes the atmosphere is conducive to studying. Beth realizes I’m struggling and she gives me needed help.

During lunch, Anne asks, if I know much about basketball which I do. I tell her, “I’ve played some, mostly pick-up games, I've played with a lot of others and helped the sister of a close friend. I've also helped keep stats in high school and now at our college.”

I am taken down to the court and introduced to Coach Jessica O’Malley who gives me a clipboard for shooting stats. The team is good and has a small lead at the half-time. Coach comes to pick up the stats and asks my opinion. Unfortunately I speak up. She’s surprised but not offended when I suggest, “They should use skills I see more natural with women. I thought if Anne and the other guards press closer to the persons they are covering, it would take their shots away. They would be forced to change their game.”

She either saw the same thing or adopts two ideas as the team extends their lead in the second half to a very nice victory. The Coach says, “We have another game tomorrow; will you be staying for that game?”

Instead of saying no plainly, I make excuses as I regularly do, “I would miss my ride back to college if I did.”

Anne overhears, “I’ll give you a ride if the coach allows me to.”

Coach then asks me to explain my comments and ideas a little more. I share, “I think college women are trying so hard to play the men’s game that they’re overlooking their own gifts and strengths.” She asks me to explain and I share, “It would be easier to show you, but I’m embarrassed. You already know far more than me. I’m sorry I spoke up.” She laughs at me trying to back out and cover myself.

Anne and five other players called back out onto the court and I have them throw looping passes, some are a higher arced throws as well as passing the ball down court in different patterns and velocities. I think I’m going to be hated as a short practice is called. Seemingly the next team is to be a bigger challenge and Coach Jessica wants a change or two in place. It only takes about forty minutes; the players and coaches like the differences.


As I walk away the Coach calls me, as I turned around the ball is on its way to me. Coach Jessica asks me to take a left-handed shot. I tell her, “I’m neither left handed nor a good shooter. She requests again this time more sternly, “Take the shot or do laps before you change.” I take a high arching shot that goes in to my amazement and joy.

Since the team cannot go out tonight we study some more in a lounge. But I’m forced to go out for dinner and a little shopping. They get me some panties, a bra and an outfit for the next day. I’m told I’ll be going to church.

I lie and say, “I don’t usually go to church.”

Anne says, “Besides being a bad liar, you are going like it or not.”

I say, “But I was only obligated to stay one night.”

Anne laughs, “That was before I agreed to give you a ride back tomorrow. And now we already have bought you a new outfit. You kind of owe us.”

"Yea, like I can need another outfit

I watch the movie “Flash Dance” with Jennifer Beals along with the others. I didn’t go to see it in the theaters because I considered it a girl’s movie. Now I watch it with a full contingent of girls dressed like one of them, go figure. Life with girls is something I am really not use to. It is fun, but not as I would have thought being a guy in the midst of all these women. Before I can turn in Anne and another girl talk to me. “Your test scores today are better academically than your performance at your college would indicate. They also correspond with some of the difficulties you say you are having.”

Then we talk about my dancing with guys and being dressed as a coed. They finally get me to acknowledge I enjoy it more than I first said. Anne asks, “Please tell us about your speech and the learning problems you have as a guy?”

I tell her, “They’ve been lifelong problems, since childhood, I don’t know how to describe them; I’m just use to living with them.”

She asks, “Would you be willing to check out the assumption with your parents that they’ve always been there?”

I’m upset and ask, “Do you think I am lying to you?”

Beth speaks up, “No, but we have someone who works with learning disabilities who thinks she can help you but she needs to know for sure if they’ve always been there or developed when you were very young.”

I say strongly but with a hint of shame, “Either way, I can’t afford counselling, other programs along with going to college.”

Anne is compassionate when she says, “It can probably be done free as part of training and research here. You’d probably know if it’s helping within one to two sessions.”

She asks me about their study time. I feel like I’m being quizzed; I state, “I did not know this was part of my obligation.”

Anne thanks me, “I thank you for being a good sport as well as helping the basketball team. But you obligated yourself when you kept playing and lost big time.” We talk a little more and then turn in. I’m awoken at six in the morning and reminded it takes a girl longer to get ready. “I will be happy when this experience is over.”

“Really,” questions Anne “Isn’t any of it fun?”

“It’s a neat experience that I won’t forget and I enjoyed it some. That is a big admission from a guy. …Well, I figured I might as well as volunteer the information; you seem to have a way to get me to share more than I intend anyway.”

Anne laughs again, “Truthfully how enjoyable has it been so far? What did you enjoy?” We visit for a while and she even gets me to confess that I had cross dressed as a kid. Thankfully I didn’t share how much I really did.

When it comes time for church we go to the early chapel service at Collegiate Church, a block off campus. Associate Pastor Ramona is conducting this early service. I get to meet her after church and she’s as personable as she is good at preaching. I feel quite guilty about being dressed as a woman in a place of God. She senses a problem; “Well Jenn, I hope to see you again and please call me if you would like to talk.”


We get back in time for a lunch. When I get back to my room there’s an outfit laid out for me. I’m told is what the support staff wears for games. This one has an ivory top, light purple jacket and long skirt. Both the top and the blazer jacket have a small pink rose embroidered on them.

Beth helps me with my make-up. I do not realize it but Beth helps me in doing my own makeup.

They’re playing Temple University in preparation for the following year when Amber University (AU), the Ambassadors, will be in Division 1. Temple already has a very good team and they are presuming an easy victory.

Amber’s new style turns it into a game. Coach asks me at half time for my thoughts before she goes into the locker room.

I ask, “Are you serious?” Finally, I share as she waits, “If Anne and the other players should be playing their players tighter on defense. They could cause Temple’s shooters to alter their shooting and get them out of rhythm.” I tell her, “Anne needs to take a few more shots, but she needs to be more fluid in her shooting and not second guessing them.”

Coach jokes, “I hope Anne will take your advice.” I didn’t know how much Anne played the previous year but stats indicate she didn’t even average 4 points per game. While she already has four points, I could see she’s better than that.

They play more of the second half like suggested the previous day. I have trouble keeping the stats as I’m distracted by my being dressed as a girl. It doesn’t help I’m also getting too much into the game. The team press on defense forcing bad shots and passes and gets expected turnovers. Anne makes 11 second half points as AU upset Temple by three points.

Unfortunately for me, Anne is unable to stop the team from pulling me into the locker room and over to the showers. She does help me to get back to her dorm room to change back for the trip to my college.


We’re riding back to Upper Valley College, Anne opens a note from Coach O’Malley, who wants Anne to talk to me. Anne says, “Coach wants you back on Monday if possible. Not tomorrow, but the following week.”

I’m frank, “I have a life and cannot make it.” Anne is willing tell Coach my answer, but Anne pulls over to the side of the road and we talk. “Brian, you are likely to do well on your exam and quiz tomorrow since you studied as you did.”

I say, “You can’t be serious? The results won’t change just because I studied with your group.”

She says, “Brian, I don’t mean to hurt your feelings. To be honest, I didn’t think you would be a good girl. Did you realize you… as Jenny, you didn’t stutter or have problems with your thoughts being understood?”

I tell her, “I don’t usually hear my stuttering and to me my thoughts are understandable. It isn’t until a test or paper is back to me that I see mistakes pointed out.”

She suggests, “Well read your notes and read the questions as Jenny but make sure you do your tests and papers writing as Brian. I would like you to consider coming back this weekend as Jenny. I am telling you the doctors, seem to think they see more under that hard exterior.”

Again I tell her, “Even if I wanted too, I can’t afford it. “

She asks, “What if they take care of expenses and pay you some every week they ask you to be there? They could probably supplement it even more by having you do things for us at the university?”

I question her, “What is this per week stuff, I thought we were talking about one more time; two or three if they could help me?”

Anne covers her tracks, “Well yes once, unless you agree to more. Some people are doing research and you might be the kind of person they are trying to help. I know it sounds strange, but I suspect what you call normal isn’t always easy.”

“Have you read my grades and researched my life? You seem to know a lot about me. I’m not sure how comfortable I am about this.”

I’m thinking, ‘The help with studies and my need for financial help is excuse enough for me to say yes. She wants me to be picked up on Friday by 1:00 pm in time to change and catch their team bus to York State University. It is an hour west of Philadelphia. It's their first official game of the season.

Anne says, “The York women’s team is a worthy opponent and it will be a good challenge. If you like excitement this should be a good game.”

“No, I don’t know how much you’re offering, but I don’t want to find I’m obligated to something with as little as I know.”

When we get to college, I agree to think about it. I speak up for my male ego and ask for a kiss. Anne says, “I shouldn’t for ethical reasons,” but she says, “I did enjoy my time with you Jenny.”

While we are about the same age, she is a year ahead of me in college and I feel like I’m looking up to her...

Story to be continued…

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