We drop Mom off at home and I quickly go to my room to get some toiletries. Mom reminds me to get fresh panties and camis, as well. The new purchases are still in the car; it seems I will be wearing some of my new clothes tomorrow to meet Vicki’s mother…

I put all of the things into an overnight bag that Mom hands me. At this point, I don’t even cringe at the fact that it is pink.

About twenty minutes later, we are pulling into the underground garage of an expensive-looking condo complex. Vicki parks in a reserved spot right next to the elevator and we get out. I take all of the purchases and my overnight bag out of the trunk and we ride the elevator to the penthouse. Vicki had to put in a special card and a code, but the private elevator opens straight into her apartment. The view of the city is stunning as soon as the doors open up and I gasp.

Vicki smiles and asks, “You like? It was my graduation present from high school. I think my Mom traded it with someone for some work she did on them. Something about a tax write-off. Anyway, it was a win-win-win, don’t you think?”

I am still gawking at the whole place and just nod. It is all absolutely stunning; the condo itself, the view, the furnishings…

Vicki pulls me out of the elevator and the doors close behind me. She tells me to just put the bags in the bedroom and points in the right direction. I go into the room she indicates and see an immaculately kept bedroom that is very feminine in its furnishings and accessories. It is all pinks and bright whites, lace and ribbons. It is all very tastefully done, though…for a woman, that is. Any self-respecting male would go into feminine-overload in here…and I am fighting it hard. It hits me hard again that this is what she wants me to embrace—what I have promised to embrace…

I set the bags down at the foot of the king size bed and hurry back out of the room; only to be pulled back in by Vicki.

She giggles and says, “We should get comfy.” She digs in the bags and pulls out one of the baby doll nighties that she had gotten me at VS. It is dark pink and silky, with lots of lace. She says, “Here put this on while I change—I will be right back!”

She disappears into her bathroom, leaving me holding the lingerie. I shake my head and get undressed. I sigh a little as my ‘guy’ is released from his strangle-hold and pull on the bottoms that go with the baby doll. Either I have become used to the feel of panties, or he is just still too numb, but I don’t get any reaction from him as I pull them up; which is good, as far as I am concerned. I don’t want Vicki to get the wrong idea… I am just pulling the top over my head when Vicki comes out of her bathroom with a similar, but black, nighty on.

She smiles and says, “Wow! That is so much better! I love my clothes, but I love relaxing in a nighty so much more! Come into the living room and we can have a glass of wine before we go to bed. It is going to be a busy day, tomorrow.”

We go into the living room where she has me sit on the couch and then she goes to the adjoining kitchen and pours two glasses of her signature red. She hands me one and curls her feet up under herself on the couch. She says, “Get comfy, Hon. It is just us.”

I try and mimic her position, but it is not really comfy for me with my guy getting his feeling back. I change positions and just bend my legs back under me the best I can.

She smiles and we clink glasses as she says, “There are ways to help with that… We can talk to Mom, if you like. I know I would like that…”

I think to myself, ”Say something, idiot… Tell her that is going too far… Tell her…” I don’t know why, I really don’t, but I say, “Yes, I would like that…if you think it is a good idea.”

She looks at me and says, “Gerri, this is not about what I want. If you don’t want it, then say so. I am not about being dominant or controlling… That is not me; if this is going to work out between us, it is a partnership of equals…and honesty.”

I nod and take a sip of wine, already feeling it, since I had had some at supper, too. I say, “OK, Vicki. I like that…and it can’t hurt to talk to your Mom, right? Just to see what the options are? If there is a way to make it more comfortable when he is tucked away, then I am all for it!”

She giggles and we finish our wine, with her snuggled up to me. It is nearly midnight by the time we finally get ready for bed. Vicki washes off her makeup and moisturizes her face while I brush my teeth. Then we go into the bedroom.

My heart is pounding, I am so nervous. I have no idea what her expectations are… Should I make a move? Do I wait for her? Does she even want to…?

I am immensely relieved when she pulls back the covers to reveal the pink satin sheets. She smiles and says, “Be careful, Hon. If you have never slept on satin sheets—they are slippery…” Then she sighs and says, “I hope you are not getting the wrong impression about our night together. I just want to enjoy us…snuggle…nothing more. OK?”

I am sure the relief must show on my face. Not that I wouldn’t want to do more, but the pressure is off… I know where things stand. I say, “That is perfectly OK, Vicki. This is perfect!”

She kisses me and says, “See! You are just so sweet!”

And I get into bed—only to slide off the other side to her immense laughter…

It doesn’t take me long to fall asleep, spooned by Vicki. The relief of not having to try and perform, mixed with the effects of the wine lull me into a deep sleep. That does not mean that I don’t dream, though. I have the most wonderfully erotic dreams of Vicki…

It takes me a bit to realize that what I thought was a dream is actually Vicki kissing me…licking me…on top of me…

I open my eyes to sun streaming in and her smiling face…just as she settles down onto my very hard and very ready erection. My eyes go wide and she leans down and kisses me as she starts rocking her hips. It does not take long and I feel an immense wave of relief come over me as I empty myself into her. I look into her eyes and she smiles at me again…but it is a different smile; one that seems to be just for me--for no one else in the world; just me…

She says, “Good morning, Sweetheart! That was for being such a sweetie last night. You can return the favor tonight. You should probably go and shower for now…”

She takes a towel and makes sure we don’t soil the sheets as she slips off of me. She gives me a kiss and says, “Go! I want time for one, too…and the way I feel right now, we don’t need to be taking one together…”

I nod and go into the bathroom and take a very cold shower for as long as I can stand it, before turning it to warm. Of course, there is nothing in her shower that is meant for a man… The shampoo, soap, and body wash are all scented for a woman. I won’t even go down the road of the ‘feminine wash’… With no other choice, I come out of the shower smelling like ‘white chocolate and strawberries’…

There is a pink, thick, soft absorbent robe waiting for me and I put it on and come out of the bathroom to the heavenly scent of coffee. I go into the kitchen and receive a bagel and a cup of coffee while Vicki heads for the shower, herself.

I have finished my bagel and two cups of coffee when she comes out; her hair is wrapped in one towel and her body in another. She fills her mug with coffee and goes back into the bedroom. I follow her and watch her put on her makeup. She smiles and explains each step of what she is doing. I know she has misinterpreted my attention for desire, rather than just wanting to watch her perfect hands work on her perfect face, so I don’t say anything and follow along with her narrative.

After she is done, she puts on her panties and bra and dries her hair. Then she asks, “So, what have you decided to wear today?”

I say, “I looked at the weather on my phone and we had our first cold snap last night. It is only 48 degrees out, so I was thinking maybe the wool pants?”

She nods and says, “Yes, that is a good idea… Why don’t you wear the dark green pullover sweater with them? You can wear a black cami under that and it will all look very nice!”

I nod and start getting dressed while she goes into her closet to pick out her outfit for the day. This is the first time I get a glimpse into it and am surprised at the size of it. It is bigger than my Mom’s whole master suite at home. If I had to guess, I would say, there must be at least a hundred pairs of shoes lining the walls…

I shake my head as I see the five new pair, still in the boxes, at the end of the bed. I put on a pair of panties and tuck my still happy little guy back. I put on a black cami, the first time I have ever done so, and marvel at the soft, silky feel. Mom had bought me black ‘knee-high’ nylons to go with my ‘good’ shoes and I put those on instead of socks. Then I take the tags off of the pants and put them on. I struggle with all of the backwards buttons, flaps and hooks, but finally get them all closed up. Then I pull the soft dark green cashmere sweater on over my head. Thankfully, the cami does not show…I was worried that the lace just might.

I look at myself in the mirror and realize that the pants sit lower on my waist than my normal ones do. The little butterfly on my butt is plainly peeking out, so I am going to have to be careful to keep my sweater pulled down.

Vicki comes out in blue woolen pants and a pink sweater of her own. The big difference being that her assets are plainly adorning the front of the sweater. She says, “Now, that looks great!” And she gives me a kiss.

I smile and say, “I have one problem, though. The pockets aren’t real… I don’t have anywhere to put my wallet or keys.”

She taps her lips with a perfectly pink-manicured finger and says, “Yes, I guess I didn’t think about that… Let me see…” She goes into her closet and comes out with a small black bag. She says, “This is a Fossil bag that is actually sold as a unisex one. You can just put your stuff in here. It is masculine enough that it won’t stand out, but feminine enough to give that little ‘extra’ feminine feeling!”

I smile at that. Not because I agree with it, but because of the irony. She, of course, takes it as ‘I love’ the idea. I say, “Great! I think…don’t let me leave it anywhere! I am not used to a…purse…”

She says, “Man bag, if you are still a bit uncomfortable with the thought. Just think of it as a man bag. OK, we really need to get going. We are supposed to be at Mom’s place in twenty minutes!”

I fidget all the way there. I am nervous about meeting her Mom. I am nervous about being completely dressed in girl’s clothes. I am really nervous about carrying a purse…

We get there and Vicki parks a ways away from the entrance. She says, “Mom doesn’t want us to take up customers’ places, so we always park further away. It also protects the cars from dings.”

We start the walk to the front door and I am still getting used to the shoes. The two-inch wedges keep me just slightly off balance as I walk and they sound different on the concrete than my normal shoes; not the same click-clacking as Vicki’s four-inch stiletto heels…but, well, just different. I had also been worried about what they would look like, but Mom had been right that the pants are designed for higher heels and the way the legs fall masks the shoes nicely…

We walk up to the door of the building and I notice it is a mix of a beauty spa and cosmetic surgeon’s office. Vicki tells me that it has turned out to be a really winning combination. Women coming to the spa often decide to have procedures. And women coming to have procedures often become long-term clients of the spa.

We go in the ‘surgery’ side of the complex and Vicki smiles as she says ‘Hi’ to the receptionist. She introduces us, “Gerri, meet Veronica. Veronica, Gerri. Is Mom ready to see us?”

Veronica nods and says, “Hi, Gerri. Nice to meet you! And, yes, Vicki, your Mom is waiting for you in Room Two.”

Vicki thanks her and leads me down a hall to a room with the number ‘Two’ on it. She quietly knocks and goes right in. I meekly follow her in as Vicki goes up and hugs a woman that looks more like it should be her sister than her mother—she is every bit as beautiful. Vicki steps back and says, “Mom, this is Gerri. Gerri, this is my Mom, Sherri Langdon.”

Dr. Langdon smiles at me and says, “It is very nice to meet you, Gerry. Vicki has told me quite a bit about you over the last couple of days. You have made quite the impression on her—and my husband, it seems.”

I blush and say, “It is nice to meet you, too, Dr. Langdon. All I can say about impressions is that your daughter has certainly made a lasting one on me!”

Dr. Langdon giggles and says, “Vicki, you are right! That is just so sweet! Gerry, please call me Sherri. Have a seat and let’s talk a bit.”

We all sit at a small conference table in the room. I quickly look around and see that it is an exam room of some type. Before I forget it, I say, “Dr… Sherri, my Mom said to tell you ‘Hi’ and that she will be in touch with you soon to set up a lunch. I guess you know each other?”

Sherri smiles and says, “Yes. Your mother and I go way back. She helped me with some real estate investments when she was working with her old real estate firm. And now, she is helping me with other investments at her new bank. She seems to really like this new job; although, I know she feels guilty at times that it takes up so much of her time… Tell her that I look forward to lunch, please.”

She smiles at me and then turns to Vicki and asks, “So, what is it that you wanted to discuss that we needed to meet in a consultation room?”

Vicki giggles and says, “Well, Mom; as I have told you, Gerri is experimenting with the feminine and there are some things that I hope you can help with before we go for our spa appointment on the other side….”

I just remain quiet to see where this is leading.

Sherri looks at me and asks, “So, Gerry, I have to ask you. Is this true? You want to experience the feminine? If so, how far? More like, what it is to be a woman? Or just, the feminine side of being a male? Looking at how you are dressed, right now, it is a bit hard to tell. Based on Vicki has said, the former?”

I always get confused with that ‘former’ and ‘latter’ stuff, but I think she is asking if I want to be more like a woman than a sissy. One thing is for sure, I don’t want to look like some sort of sissy. But I have no plans on being a woman, either.

I sigh and say, “It’s true, Sherri, that I am experimenting. I honestly don’t know how far to go, but I do know that I don’t want to be a ‘sissy’. I know that is likely not the best word to use, but…I don’t want to be laughed at…”

Sherri gives me a genuine smile and says, “I understand; and that word is fine, for now. So, what I am really hearing is that you want to experience being a woman, then. I know you are still in school and we have to be careful that what we do is in line with whatever is allowed there. There are a couple of options, really. We can work on something that will put you completely in the realm of the woman—full time. Or, we can do some things that will allow you to switch back and forth—those things are not as realistic in terms of the feeling, but are a good beginning. It seems that may be more what you are looking for?”

My head is swimming. I have no idea where this is headed. I say, “I think so. If I understand what you are asking; no, I want to be able to be ‘me’ at school. I…I…I don’t want to even think about what it would mean to go to school looking like a girl. When Mom suggested I wear things like this to school, I got all nervous!”

Sherri giggles and says, “Well, Gerry, those are certainly very nice clothes, but the look is still very androgynous the way you are dressed, at the moment. More importantly, it seems your Mom knows and is supportive of this, as well? I know you are eighteen, but family support is important.”

I just nod and say, “Mom is actually very insistent that I go through with this ever since I said something about it. She seems to think it is important that I do…”

Sherri frowns and asks, “But, she is not forcing you, is she?”

I shake my head and say, “No, she left the choice completely up to me. But, she is adamant that I follow through, since I chose to do it.”

Sherri says, “Yes, I can see that in your Mother. She is very conscientious; and when she sets her mind to something, she follows through. She obviously expects the same of you. So, you are sure?”

I look at Vicki and smile; then look back her and say, “Yes, Ma’am.”

She says, “OK, then. Here are your options, as I see them. If your intent is only to make tucking easier, then we can give you a blocker that will prevent you from getting an erection. That will make things much more comfortable until you decide if and when you want a more complete and permanent solution in SRS. If you also want to emphasize your female slash feminine feelings then we can add female hormones to the mix. But remember, hormones alone will not make you feel feminine—that is a mindset; they will simply help give you a better foundation to get into that mindset. I am not really willing to give you hormones without a blocker, though. I have seen that mess people up too much. Effects of either of the above options are reversible up to a certain point—if you continue this course for too long, reversing the effects will become more and more difficult until no longer possible. Do you understand?”

I listen, stunned. I had not even contemplated that it would take this course. I don’t really know what I expected. My head is spinning, so I decide to ask some questions. I look at Sherri, “So, what…effects can I expect and how soon? How long is a ‘while’?”

Sherri smiles and says, “Good! You were paying attention! For the first couple of months, you will experience the effects of hormonal change; much like a woman experiencing pregnancy. You will likely experience some nausea for a while and struggle with your emotions running wild on you. Of course, the intended effect will also present itself in that it will become increasingly more difficult to get an erection. You will find that the estrogen will counter that in ways of its own. If you continue the course, your skin will become softer, your fat will redistribute to more feminine areas, your hair will become softer, and your body hair will become finer and sparser. Eventually, you will develop breast buds and then full breasts, although not as big as if you had started this earlier…”

She gives me a look to see if I am keeping up. I guess my look satisfies her and she continues, “As for when this will all happen; well timelines vary with each individual, as does the actual extent of developments. We will need to take some blood and other samples to see where you currently are and adjust from there. As for when the point of no return is reached, that is somewhat dependent on everything else I just described, but is typically measured in months; maybe six and closer to a year for some.”

She sees my confused look and says, “Gerry, you don’t seem too committed to this. Do you want to think it over? Discuss it more with Vicki—or your Mom? Your Mom doesn’t technically have to be involved, since I will cover the costs and you won’t have to worry with insurance, but I fully understand if you want to discuss it.”

Vicki takes my hand and says, “Hon, no one is pressuring you into this. If it is too fast, then we can wait. I just thought it would help with your problem and help you feel more like you want to.”

Sherri looks at me and says, “Absolutely! These are only options and you have to decide. I will say, however, if you decide to go with them, I insist that you stick with it for at least three months and give it a chance. Even the most dedicated struggle with the initial effects and if you don’t get through those, then you will not have a chance to embrace the benefits.”

I sit there for a few minutes and just think. I let my conversation with Mom go through my head. I sort through my feelings for Vicki. I ask myself what I am willing to do. Finally, I come to the conclusion that three months can’t be that bad…right?

I nod and say, “OK, I have to say this is a surprise. I didn’t know what to expect when I came here and this is a bigger decision than I was expecting to have to make… I don’t need to discuss it with Mom, though. I think I would like to go through with it for the three months and see how I feel at that point.”

Sherri nods and says, “That is what I wanted to hear, Gerry. No, not that you want to go through with it, but that you are not taking this lightly. Now, we just need to get some samples…”

Vicki and I walk over to the spa side of the complex. I had to give a blood and a semen sample and then Sherri had sent us on our way. Now, Vicki is signing us in for some appointment that she seems really excited about.

She bubbles, “Now, this will really get your feminine juices flowing—there is nothing like a pampering at the spa! Well, except putting on sexy lingerie after the pampering! And maybe shoe shopping… But, I digress. Anyway, we are going to get a full body wax and a mani-pedi today. We can add a little more on each week as you get more comfortable with things. Does that sound OK?”

I can’t help but ask, “Body wax? As in remove my hair?”

She giggles and says, “Yes. Don’t worry, it does hurt a bit the first time, but just wait until you are smooth. I can’t!” She whispers in my ear, “You will see why when we are in bed together!”

I won’t go into the detail of me certainly sounding like a girl when my hair is ripped out by the roots. Suffice it to say that it is not pleasant. When they rub in the soothing lotion afterwards, well, that is nice, though. And when I get dressed again… Well, Vicki was right—the soft clothes feel heavenly on my sensitive skin…

Then came the mani-pedi. I really did not know what to expect going into this. I will have to say that it was a really nice experience, though—especially compared to the waxing. When Ginger, my spa-technician, is done, I have very well-cared for nails…in a pale nude pink. I was worried when she started putting it on and then baking it under some sort of light. But,you can’t really tell, except they are really shiny now—which I am told is not unusual even for guys. At least they are short, not even close to the tips of my fingers; although Vicki seems to think I need to let them grow… I am not sure how I feel about that.

We are sitting back in Consultation Room Two with Sherri fifteen minutes after Ginger is done. I can’t help stare at my nails as I sit there.

Sherri smiles and says, “Those are very nice, Gerry. By the way, is that what you want to be called? Gerry…maybe Gerri with an ‘i’?”

I say, “I…I don’t know! To be honest, I have not really thought about it…” I think a minute and say, “Don’t laugh, but I have always liked…Deirdre…”

Vicki says, “But, that is a beautiful name! Irish, right?”

I nod and Sherri says, “Maybe you should talk it through with your mother, but I think it is lovely. Are you ready for the shots?”

I nod…suddenly very nervous.

Sherri then gives me two big shots in the butt and hands me a bottle of pills with written instructions on taking them. She then hugs me and says, “Welcome to womanhood, Hon. I hope it turns out to be all you envisioned.”