Wednesday, December 15, 2010

Christmas Picture

OK, I've managed to post two times in 8 days. That's better than I've done in awhile. I realized when I posted about Colleen, people would wonder if I was letting her beat me at wrestling and if I was being beaten. In answer to both questions, yes I use my full strength. Unfortunately, I'm not strong enough to take it easy on her or anybody for that matter. Also, it's just playful stuff that a lot of couples do, she just likes to end up on top. She's very feminine and in fact a lot of people would call her a girly girl, but she enjoys making me feel more and more feminine and stereotypically weaker and weaker. Things aren't going bad though. I think my relationship with her is one of the best things I've got going right now.

Tuesday, December 7, 2010

Pressure

This isn't a real new picture, but after a couple of formal gowns and a lot of Halloween costumes, I thought something more casual was in order. Thanksgiving with Colleen went well, but the second she had us alone she had me dressing up. I think it's taken me a few months to reallize that she the dressing is one of the things attracting her to me. I don't know how I feel about it, but I feel very lucky to have her attracted to me so I'm going to have to work on it. She definitely wants a role reversed relationship and takes great joy in acting as the man calling the shots and such. She always wants to wrestle and this isn't like Heather who can kick any of our asses in 3 seconds. I used to let her win, but frankly I don't have to do that so much anymore. She really enjoys pinning me down and enjoying her power. Though her real power has nothing to do with physical strength.

You heard a bit about our adventure as bunnies in the guy's dorm. It was scary. It's amazing how many people are up at 3AM in a college dorm and not really amazing the reaction guys have to a couple of scantily clad bunnies on a scavenger hunt. We told them it was a sorority stunt and they were extremely cooperative. Both Jill and I had to do a bit of kissing, but it was purely on the cheek stuff.

Tuesday, November 16, 2010

Homecoming

Homecoming went well, but it was pretty crazy. My date didn't know about my gender, although I got the feeling he really wouldn't care. I got the impression he might be a bit bi and I seemed to be there as arm candy and companionship as much as any hot and heavy romance. That was fine with me and I didn't have to worry about groping hands or anything. I am surprised they haven't done something with the Homecoming photos, but there's at least one picture for you. As you can see, I had a very curve hugging dress and had to wear a padded pantie to really make it work.

My grades are outstanding right now. Midterms were poorly timed, but I did well, even more so on the paper that I had than I did on the tests. I'm doing Thanksgiving with Jill and Colleen this year and I'm a bit nervous. Things are going well for me at work too. I've gotten a lot more relaxed with what I have to do and the discount has certainly expanded my wardrobe.

Tuesday, October 19, 2010

Feeling Better

Sorry, I haven't posted lately, but I've been sick for over a week. I'm finally feeling better at least. Work continues. They still want to bring Xiu into the shop when I'm working, but my illness kind of delayed things. Classes are going well. I guess I'm used to showing up in a skirt now because I'm focusing regardless of what I wear. I don't have a whole lot to report other than being sick isn't much fun.

Getting Lost in Girl? Yeah, I think it could happen. We're not transsexuals. We're also not guys putting on a dress for Halloween and that's the end of it. Living 24/7 as a woman is tough for women, even tougher for us. There are times when being a guy, even if I'm wearing panties, hose, and a bra is nice. Some people obsess over gender, but it isn't that huge. It's easier to say that this year when I have Colleen around, but we all eat, sleep, talk with friends, work, study, want to be loved--male or female.

Am I a Girl in the Bedroom? Yes, sometimes. It changes depending on mood. I'm not going to write too much about it for fear of torturing Jill, but I've been male and extremely female in my relationship with Colleen.

Monday, October 4, 2010

The Stripper

By now many of you have seen the picture of me with the stripper at Sheila's party. For the most part, the party was OK. I was very nervous around the stripper though and not really excited to have a guy wearing barely anything in that kind of proximity. Yeah I've kind of made out with guys before, but never had them that undressed.

I remember a time when I was the hot sissy. Jill said when she saw how I looked all dressed up, she was actually a bit jealous, but first Amber and now Xiu really put me to shame. Xiu's reputation preceded her, but she's just so small and delicate. It is kind of a mind trick I've learned. When I dress as a guy, I don't want to look unisex, I want to look manly. However, when I'm dolled up there is a bit of competitiveness. Especially, having a girlfriend who enjoys me being pretty.

Here's the work photo everybody wanted. I really needed a lot of Fall clothes so the discount is coming in handy. Xiu will be able to take advantage of it too when she needs a wardrobe. The job is a bit embarrassing, especially when a girl drags her boyfriend or husband and they look so bored while I have to ramble on excitedly about our merchandise. I am learning a lot about putting an outfit together and how to shop.

Wednesday, September 22, 2010

Batter Up

I always feel a bit embarrassed when I have to do something femininely that I can do quite well as a guy. We weren't playing ball inside, but even picking up the baseball bat I had to stick my butt out and act clueless.

Work has started for me, but I haven't worked long enough to have a huge opinion about it. Unlike Jill, I've worked a lot over the past 5 years so it's a little less of a shock to my system. The girls are demanding, but not particularly mean or anything. I'm learning a lot about women's clothes and I guess I'm going to have to learn a lot before they will let me actually wait on customers. I usually ring them up at the cash register and stock shelves so far. There will be a lot more posted on the new job when I have more to tell you.

Monday, September 13, 2010

New Job

I got a new job. They tried to do with me what they failed to do with Jill, namely give me a job that would embarrass me. I think they have succeeded although there won't be any guys involved. I will be working at a woman's clothing store whose name will remain our little secret. The boss knows I am a guy, but believes I am a transsexual. She has seen me and has told me as long as I maintain a professional and feminine appearance we won't have any problems even if somebody reads me. As is the case with Jill, there are several girls there who know the truth and know me from when I was just starting to build up my wardrobe. They have assured Colleen that they will report anytime I am less than 110% feminine at work and have promised me that we're going to have a lot of fun on our lunch breaks and in general. It took a long time to find a job. I was looking for awhile now.

Monday, September 6, 2010

Happy Labor Day

This is a real busy time. Classes are starting up, college football games are starting up (and it's not just about sports, but parties), and even sorority rush is starting up. Not only is Colleen thinking of going through it, there is a possibility that the girls' friend who is in a sorority may have a plan for us.

Classes are going well. I've got at least one of the girls in each of my classes. Somebody asked about me passing as a guy. Yes, it is harder now than passing as a girl. I have to dress practically 24/7 already, but honestly if I was just running to the drugstore or something I'd probably just touch up my makeup and throw on a skirt. It's a lot easier than trying to figure out how to make my hair and eye brows look masculine. There also is the matter of smell. Using feminine body wash, shampoo, and perfume, has all three of us smelling a bit girlish.

Amber is doing a bit better. She's definitely getting used to things, about as well as anybody can. She's still scared to death of going to class as a girl though.

Wednesday, August 25, 2010

So, where was I?

It seems that some ideas that came out of one of the blogs, may be making things tough. They've told us that as soon as they get the rules set and find a way to make it fair for Amber, they will be putting us through a series of sissy contests. Colleen has talked about taking me on a double date with her and 2 guys so she could watch me squirm. Things are getting tough I have to admit. I'm exhausted now after a long day of shopping and a night of modeling new and old outfits. I may have a line on a job. I will tell you all about it later.

Wednesday, August 18, 2010

Colleen is Here

I'm sorry that I have been so late in posting. It's been rather hectic and unfortunately, while I do have computer access at home, as you might imagine posting to the blog is definitely something that I wanted to do in private. Wendy was true to her word and my parents weren't overly concerned by my looks.

Colleen and Kristine have moved on down here and are attempting to do a blog together. They won't make any promises on how often it'll be updated, but they are going to try. I've already been warned that if Colleen posts twice before I post once, I will be spending a day hogtied or suitably punished in another way.

Their blog's URL is http://oursissyville.blogspot.com/

Thursday, August 12, 2010

Hello, Be Prepared to Hate Me

Be prepared to hate me, but I wanted to introduce myself. I'm Colleen and I am both Jill's sister and Cindy's Mistress. I don't know if I'll set up my own blog. It kind of appeals to me, but I am already starting to worry about the time commitments. I am so excited about college that I don't want to waste the time sitting over a computer typing. We'll see.

I love Cindy and dating her is definitely something I was never prepared for, but by trial and error I think I've figure out how to be a stern mistress and a loving girlfriend at the same time. It is so much fun!!

The chastity belt is staying, but don't feel bad for Cindy. I gave her a choice. She's dating a horny 18 year old girl whose exploring her own sexuality---me! That means little Cindy will be getting plenty of attention. The chastity belt I put on her is extremely expensive and also gives her a totally flat front, which is real useful.

I enjoy sharing her with you, but just remember this is my kink and not your fantasy. If you think I'm too mean or too nice, I'm sorry, but that's my prerogative. I'm going to do things to Cindy you won't like--nothing permanent, but she's my toy and I will play with her. I'm not going to break her though. I love her too much.

I also am an important part of Jill's life. This past week, I outed Jill kind of to our mom and to a lesser degree to our dad. My parents are actually really cool and Jill's experimentation isn't really that big an issue. Jill had reached a part where she couldn't hide how feminine she had become and I didn't want that causing her to avoid our mom and dad. At first she thought I was the biggest bitch for doing it, but she thanked me later. Mom and dad don't know everything, but they do know she's experimenting with crossdressing. I'll let her tell you the rest. They know she's dating Kristine so they don't think she's gay, but then again they really wouldn't care as long as she was happy.

I had her model some of my mom's old 80s clothes for her and her wedding dress. Dad didn't see that part, which may have been too much too soon, but mom though Jill was really cute and said she Jill looks like one of my aunt's.

That's it for now. I hope you don't hate me too much now. I promise you Cindy's in good hands and in good handcuffs too. Yee-haw!!

Tuesday, July 13, 2010

Update

I'm back and settled in a bit. The news of Wendy's wedding still has me floored. I'll discuss it more with her this weekend when I have my next appointment. In some ways having Colleen here in the Fall will be a huge improvement, in other ways it's going to be really difficult. Jill is even more confused by having her baby sister with tremendous power over her. I promised some answers, so here you go:

1. Were you actually having a good time or was it just an act at the BBQ? It was really embarrassing to be there, but of the people there I really only knew Colleen so that made it a bit easier. I guessed I'd say I started out acting like I was having a good time, but by the end of the party I was.

2. Can you earn more than 1 Girl Point? Yes, it just isn't easy. I find that slow and steady wins the race. My appointment with Wendy may earn me 4 points. Agreeing to be a bridesmaid earned me 2.

3. How did you get such realistic cleavage? The key in this case isn't breast forms, it's the less is more theory. Basically, you're only seeing a bit through my arms, which tape helped to make appear a bit fuller. You'll see the rest of the pro pictures soon.

Monday, July 12, 2010

I'm Back

The reason that I have not approved questions is because you ask a lot of them and I want to answer them all. I'll approve them tomorrow and answer. I will answer two questions that I got a lot now--It's not a CB. It was a Neo-Stell Shemale device that was designed to make me look extremely flat in front even in a tight skirt. It didn't work so well and it's in Germany now being adjusted. The reason that I gave up my masturbation privileges is because Colleen was considerably more appealing to me than masturbation. She got me extremely horny and then made the deal with me, but even without being driven by my lust, I think it was the better deal.
It has made things with Jill a bit odd with me dating her sister, but at least she knows I'm not mistreating her or taking advantage of her.

Wendy dropped a bombshell on us today. She wants the three of us to be Bridesmaids in her wedding. I guess as a stylist, she had several gay male friends she wanted as groomsmen and wound up with 7 groomsmen when she added her fiance's friends. Meanwhile, she only had 4 friends she really wanted as bridesmaids. She got the bright idea of adding us to the wedding and we don't have a lot of choice. It's a bit odd to me and I'm really nervous about the "real" bridesmaids. It's still a long way off, but our newest sissy Amber seemed really upset about it.

Wednesday, June 30, 2010

Hello from the Road


I've been through a lot since I went home. Any hope of a rest from being feminized went out the window rather quickly. At the same time, I can't completely complain. I know you've heard about the handcuffs, and the ballroom dancing, and the photographs. However, Monday night was probably the biggest night.

Colleen chose Monday to lock me into what amounts to a modern chastity belt. I was tied up and helpless at the time, but she later gave me a choice to have it removed and I didn't. It's going to be part of the price for being with Colleen apparently.

She has told me that come this Fall, removal will require me to earn "Girl Points" and she has started that with me this week. I need 10 points to get it removed and I've earned exactly 3. 1 for going shopping on my own for new shoes, 1 for going out with an old high school friend while wearing my feminine underwear, and 1 for picking up an issue of Cosmo on my own to read. The belt is uncomfortable to wear and requires me to sit down to pee. I was doing that anyway, but I now have no choice. I am getting a bit used to it at least. For the next two weeks, don't expect me to get much chance to post. Obviously, there will be a lot to tell you when I get back.

Monday, June 21, 2010

Going Home

Tomorrow, I see Wendy. I have no idea what she can do with this hair to make it look masculine or even unisex without losing a lot of length, but she assures me she is a miracle worker.

On Wednesday I go home and I'm so terrified just walking in the door. I don't have to have a bra on for the big hugging, but I will be putting one on soon afterwards and I will have hose and panties on at all time. I really worry that I will be bombarded with questions. Colleen assures me that her presence in things being introduced as my girlfriend will make my parents think it's nothing serious. I hope she's right.

Colleen isn't my girlfriend, but we have some kind of relationship going on. I know she's going to have a lot of fun at my expense when I go home, but I'm still looking forward to seeing her. Kristine and Elizabeth less so, but they will be far nicer to me than they are to Jill.

I'm about 15 miles from Colleen's house and close to 20 to Kristine and Elizabeth, so it isn't like they will be around me all the time, but they will be checking to make sure I'm pantied, hosed, I'm silky smooth, and my toes are painted the whole time I'm home. They will also be arranging excursions as Cindy that will require me to go to their place or some other private area to change. The list of things they want me to bring home is scary and includes handcuffs, a remote control vibrating butt plug, and a lot of lingerie as well as heels and makeup. I'll only be gone for a week, but this is a scary week. It will be nice to see my family again assuming I don't get caught and it will be nice to see Colleen again assuming she doesn't totally destroy me.

Sunday, June 13, 2010

The 6th Mistress

I have found it rather funny as I've watched people look for who will next join the group of mistresses. Sue is obviously the 5th Mistress. However, this whole thing started with 4 friends. You can add in Jill's ex and his sister Colleen who I confess to having a thing for myself. However, nobody has really talked about the woman who is actually our 6th mistress--Wendy.

Wendy is the woman who does our hair and has taken both Jill and me slowly from masculine hairstyles to rather feminine ones. She doesn't tie us up, post online, or do things like that, but make no mistake she enjoys the power to turn us into her projects. She's already requested pictures of Amber so she can see what she can do to her in the future.

I'm going to be going home in a couple of weeks. You can relax because I live close enough to Colleen and Kristine that they will be paying visits and making sure that I am following something of a sissy regimen, but I need to appear masculine and you know with my current hair that's pretty impossible. I talked to Wendy about it and she promised me she could make my hair look masculine without losing length and have it meet with the girl's approval on my return--her price silk wraps and extensions for a month when I return. I don't so much choice. Wendy is older and though she has made it to parties, she isn't involved in our day to day lives, but there is no question that she's running at least part of this show.

Tuesday, June 8, 2010

Working Out

I've signed up at the gym. Heather wanted a workout partner and decided I fit the bill. She's actually working on a program for me--light weights and heavy repetition. She has warmed me that I'll be more toned, more flexible, and leaner. The idea is that my workout will just make me even more feminine. I don't know if it's possible, but I did notice guys checking me out when I was on the elliptical machine today. It seems like one more indignity. I see guys lifting weights and know that it isn't for me.

Friday, June 4, 2010

Tom Update

Tom and I have settled into a rather odd symbiotic relationship. After that hot and heavy kissing at the dance, I'm basically serving as a girl to hang out with over summer with his girlfriend away. I can serve as his plus one and we just basically hang out so he's happy.

For me, he's a true gentleman. He's fairly safe and Karen basically told me, "you need to learn to carry yourself as a lady when you are with a guy. Do you want to stick with Tom for awhile or do you want us to set you up." I think Tom is the easier choice.

While the kissing is not as passionate, I am basically going out on dates with a guy who I am acting flirty and feminine for. The girls are thrilled that I am regularly being put in this spot.

This is obviously not an ideal situation for me, but the closest thing I've had to a girlfriend since this has begun is using the picture of me kissing him as her desktop supposedly. I guess it's working for everybody so far though sometimes I find it hard to believe I'm going through with it.

Wednesday, June 2, 2010

Maid Questions

I mentioned that I was doing 5 apartments on a weekly basis as maid.

1. Our own
2. Peter and Dan - Friends of the girls. My first date with a guy was Peter.
3. Sheila and Karen
4. Amanda and Heather
5. Sue

These are the regular ones. There are a few others that I'll tidy up after a party or if a parent is visiting.

Q: I hope your barbecue was a success. I assume nothing blog worthy occurred.
A: No, nothing really major. Jill was going to write about it and other things came up. We had a lot of rain, which didn't help.

Q: You mentioned Karen's boyfriend treats you OK. Are you around many guys that are aware of your sissy status? Do any of them tease you or have the girls protected you from any abuse?
A: There are 8 or 9 guys who know and the girls do protect us to the point of threatening one of them with his own makeover if he didn't knock it off--it was funny who quickly he changed his tune. They do tease a lot, but the girls have been very careful with who they've let in on it--thank goodness. The guys who know are not neanderthal types.

Q: After reading Jill's latest blog, I feel there is quite a bit you aren't sharing. I realize it can be embarrassing, but this is a blog about sissies dominated by women.
A: I'll try. It's hard to admit everything.

Tuesday, June 1, 2010

My Day Off?

As you know, Jill is working pretty close to full time it seems at the restaurant this summer, while I am serving as maid for 5 apartments and undergoing a crash course in femininity. I'm actually probably getting more instruction that Jill ever got. It's gone past doing my own makeup to being given a scenario and creating a look for that scenario. If I'm going to class in the daytime, I'll have a light fresh look, but an evening date will require me to spend a half hour just giving my eyes the right smokey look.

Today was supposed to be an off day without an apartment to clean. A brief discussion of a wedding that Amanda will be in later this summer, turned into a trip to the bridal shop for Amanda, Heather, Sheila and I where I played the part of a bride to be browsing wedding dresses and the girls were my maids of honor. They've done this before mostly with Jill, but last time Heather went home she borrowed her sister's engagement ring--bad breakup, cheap ring, so she was happy to give it to her. When I slip on the engagement ring, it sort of adds more credibility to the story. I don't think I've always been able to pass in the bridal shops, but people have always been most friendly as long as the girls don't crack up too much. This afternoon was spent browsing and trying on a lot of white lace. Not quite how I expected my day off to go.

Monday, May 31, 2010

Happy Memorial Day

Happy Memorial Day to the men and women who are doing the extremely difficult jobs overseas to keep us safe in the armed forces and the many brave men and women who have served honorably over the years.

The girls bought Jill and I military style outfits, that are anything but regulation. Aside from feeling like Armed Forces Barbie, but I really dislike having my stomach exposed. I'm not used to it and I'm constantly trying to pull down my shirt.

This whole thing started with Sue this time who asked if they dress us up special for the holidays. I hate to think what they have planned for 4th of July. Anyway, we're barbecuing today. It won't be a huge party, but the girls have decided that it's important we host these things because it'll be good for our reputations.

Friday, May 28, 2010

Last Night's Date

I went on my second date with Tom last night. It was pretty tame by comparison to the first one, but I have to admit that I felt a bit silly showing up at his door in my frock. The date was something simple this time. His fraternity was having a pre-Memorial Day barbecue. The house was rather empty with so many students home for summer, but the dozen or so who stayed behind provided food and drink. There are a lot of things you learn about dressing up the more you do it--high heels don't work well with grass. I was told by Karen that wedge heels are the way to go. She was naturally in jeans and sneakers. It was a safe environment, which is important with both Matt and Karen watching us. After dinner, we went for a walk and yes we did hold hands, but basically we made small talk and he also explained his situation with his girlfriend. For now I seem like his summer plus one. I really don't want her to find out about me, but I don't see how she won't.

Monday, May 24, 2010

The Kiss

I'm kind of at a loss to explain exactly what happened on Saturday night, but I will do my best. To begin with I have discussed things with Jill and she told me that she has experienced a similar thing though not as embarrassing where you are so desperately trying to convince everybody that you're what you appear to be that you lose yourself in the character. This is not uncommon with actors and what we do is far more personal. Yes, I did get caught up a bit, but that doesn't make me attracted to Tom (Not Sue's boyfriend by the way) or to any other guy.

The kiss itself was an open mouth kiss that he initiated. I was tipsy and he was definitely very drunk by then. It's a very awkward situation to be in because you are trying to flirt and make him think you are a girl and that you are into him. You can't exactly knee him in the balls if he tries to kiss you. I should not have opened my mouth then. We did kiss several times throughout the night, but this was the only open mouth one. He did put his arm around me in the car, but we didn't exactly make out--he would have known if he had gotten too close.

Yes, I did feel his penis when we were dancing. I would guess about 8 inches--definitely bigger than most. I don't know if that's common or not, but I definitely felt it. In answer to questions I've been asked--I use a gaff to keep my penis from causing a bulge, but I was not excited during the evening. Yes there was some bumping and grinding on the dance floor.

I'm no expert on passing, but I would say what helped in that situation more than anything was that we didn't make a ton of real close contact before he had beer goggles. There is a pro and a con to that as while he may get less perceptive, his inhibitions loosen too.

So in answer to the big questions--yes there was tongue and no I was not turned on. I don't deny that I did get carried away and probably did more than I had to or should have. I'm going to have two more dates with him and we've talked on the phone since. I've taken full responsibility for the night apologizing for taking advantage of him with his girlfriend out of town. That should tame things down a bit for later in the week and we've agreed to go out again as friends. I guess he has an understanding with his girlfriend over summer.

I have wondered if Kristine reads the blog since she never posts, but I've received several texts from her totally enjoying it and teasing me about the whole thing. Some of you are way too quick to try and get me in trouble. I had tonight to get my thoughts in order and frankly I needed it.

Saturday, May 22, 2010

Dance Tonight

Karen's boyfriend Matt has always had an odd relationship with me. At first, I was worried he'd be jealous--afterall his girlfriend had seen me naked and barely dressed on several occasions. However, he seems to get kind of a kick out of his girlfriend and her friends being able to dominate and feminize me. He does not try and dominate me, but when I greet him, Karen and Matt have made it clear that he should get a kiss on the cheek from me. I've also had to do his laundry when it's been left over at her place and I've made a bed knowing that he just slept in it, so there is an obvious pecking order between us.

His Lacrosse club is having a dance tonight and one of his friends had his girlfriend go home for summer and she was unable to make it back. So last night, when I'm just relaxing and watching television, I was a little surprised to find Matt, Karen, and his friend Tom at the door. As they sat down, I served them beer and got one for myself. We keep beer in the fridge, but it is only there for when guests come over. They explained the situation to me and I couldn't really do much. I made a lame comment about not having anything to wear and Karen told me we'd take care of that this morning. I had no choice but to agree.

Today I bought a new dress for tonight. It's soft pink with spaghetti straps and a tiered skirt. I also bought a pair of white strappy sandals with heels. We then went for manicures. The girl who did it suggested that I might try silk wraps next time and Karen said she thought that was a great idea too. The girl who did my nails seemed very nice, but it didn't take her long to figure out Karen was in charge and asked her about polish color instead of me. We went with a pink that matches my dress.

Tuesday, May 18, 2010

Careful

Be careful please. What you say has consequences and all of you saying punish Jill and Cindy if they don't blog more are being very unfair. We have a ton to do. I'm cleaned 3 apartments today. I also spent time practicing my walk and I'm constantly practicing this or working on that. I try posting as much as I can. It isn't easy to talk about exactly what's going on. I can barely believe it. Instead of going behind my back to Sheila and Amanda, why not give me suggestions of what you'd like to read about?

Tuesday, May 11, 2010

My Appearance

The girls have assured me that I'll be so happy to have this hair when I don't have to wear a hot wig all Summer, but until I finish finals this week I'm mortified. I can't make it look manly in a ponytail because there's not enough hair for a ponytail. I can't comb it in anything resembling a guy's style so I'm going to class in a baseball hat. When I see myself in the mirror now I can't believe it's me. I was asked what my family thinks--they don't know yet, but I don't have any idea how to either hide this or make it look like a masculine cut. Since this started, they have loved to find ways to put me in inescapable femininity. This is the ultimate because even I find boy clothes, with this hair I'm still going to look more girl than boy.

Friday, May 7, 2010

Freaking Out in the Chair

Not good. We obviously read each other's blogs. I especially read to see what the girls are saying about me so when I read Jill's last post about her hair in Sex and the Sissy, I knew that I would be getting my hair cut in a beauty parlor, but it still didn't prepare me for what was to come today. As I was led to the chair by a trio of giggling girls--I was terrified. Heather, Amanda, and Sheila sat me down in front of Wendy who gave me a big smile and handshake and then observed me really closely.

As Jill has mentioned, Wendy is cool with taking care of our hair and doesn't even care that we're not exactly there willingly, but she doesn't want us to cause any problems for her at work. As she explained that my hair was definitely long enough to do something with I started to panic. I immediately felt Heather's hands on my shoulders. She must have sensed that I didn't feel like staying there. All four girls including Heather made it very clear in a very subtle way that my best option was to relax. I couldn't help, but freak as I saw my hair taking on a feminine appearance. They were all overjoyed with how it turned out and informed me that as my hair grew longer the style would change. I can't figure out how to make it look masculine. I can't even do a pony tail with it.

Saturday, May 1, 2010

The Long Walk

Before we left for class Friday afternoon, Heather spied a bottle of Jill's nail polish on the end table. It was a very soft pink that was barely noticeable. She looked at me out of the corner of her eye and then despite my protests she had me spread my fingers out on the coffee table and began to paint. As I blew on my fingers and shook them to dry, I knew I'd be hiding them all class.

As Heather, Amanda, Sheila, and I headed over to our class Heather started commenting on how much she loved my shoes. As these were just simple gym shoes I knew I was in trouble. As we passed a bench she had me sit down and asked me (read that as ordered me) to sit down and switch shoes with her. I tried to put on the women's flats I was given over my socks, but I was soon corrected by Heather who told me, "If you want to wear socks that's fine, but only to fill out your bra." Needless to say, the socks wound up in my book bag and the shoes showed off my pantyhosed feet.

We only walked a few more feet when I was forced to trade belts with her. She got my simple black leather belt and I get her metallic silver one. Being partially feminized is the worst. You have no prayer of passing and at that moment I would have much preferred to be in a little black dress and stilettos than in half male, half female mode.

Thursday, April 22, 2010

Where We've Been

Things have been heating up for Summer. So far Jill hasn't had much luck finding Summer employment that meets the girls' specifications and we had a hard time finding an apartment. We have found a two bedroom with rent at only $600 a month, which isn't bad for the two of us. We have painted, moved, and dealt with all that. Although we signed for our apartment under our male names, the plan is to live together completely as women once classes end. Our lease technically starts May 1st, but we've already done most of the work.

Saturday, April 10, 2010

Spring Break

Spring Break was certainly not what I had planned. Not long after I started having to dress, I was instructed to call my parents and let them know that I'd be spending my break at a friend's house. That friend was Jill. Now, I'm normally very nervous meeting a friend's parents, but I was petrified doing so knowing I had on a bra, panties, a camisole, and pantyhose with painted toe nails and a suitcase full of lingerie, makeup, and even some female outerwear.

I spent the week as Jill's sister's project and if anything she was tougher than the girls at school. I'd be up shortly after Jill's parents left for work every day, so that I could serve breakfast in bed. The mornings usually consisted of chores while the afternoons consisted of shopping. I have not been out much in public and at least I got to go out where most people don't know me, but there's a big difference between looking cute in a picture and passing when you speak and move. I've been told that I need to start focusing more one learning how to act and move. I don't see much choice if I'm going to constantly be out in public.

Tuesday, March 30, 2010

It's Not As Easy As You Think

I know how hard my current situation is for you all to understand, but if you're one of the people who keeps saying, if you wanted to, you could get out of this please think for a second. Usually, right after telling me that if I stood up to the girls, I could get out if it without any trouble, they'll tell me they don't think I want to get out. That is exactly the attitude that my friends will have. That's exactly what I'm nervous about. My friends, family, and people at school will always be wondering if I wanted to do this.

The girls responsible for feminizing me are all very attractive, but they're also extremely cunning. They have so much to blackmail me with now. Some people have even told Jill and I that 4 girls can't overpower one guy. Even when the guys in question aren't that big. That's a picture of Heather. She's now a blackbelt in judo. She doesn't use physical force on me or anything, but it sure we no trouble for the girls to get me tied up or to control most any situation. Now, don't get me wrong they don't physically threaten me or anything, but that's just another thing that makes escape hard.

Friday, March 26, 2010

Tonight Will Be Humiliating

I really am still not so sure if I made a good deal by going so far with the girls in exchange for not having my friends shown pictures of me. I asked Jill about it and she told me, it isn't a question of whether your humiliated or not. If you have any male pride, you are going to be very humiliated. What you need to ask yourself is do you want to be humiliated in front of these girls and some of their friends or do you want to be humiliated in front of your own friends.

Jill and I took off from class today to get manicures and pedicures. Jill even had some work done on her hair and we had our eyebrows neatened as well. It was a major embarrassment even if Jill had been there before and had at least something of a rapport with the stylist. The girl who took care of me was only 18 and couldn't have been sweeter. I actually felt kind of bad and gave her a big tip, but I just felt so embarrassed as I saw that brush go into the polish and come out dripping red and watched my fingers one by one receive the treatment.

Jill and I then spent all afternoon working on looking our best. Scented bubble baths, painstaking making application, you name it. Now we'll be heading out to set up the party. I have received instruction on how to curtsy and say "Yes Sir" and "Yes Ma'am". I can't think of anything more humiliating then doing this party and trying to act so feminine. I just keep thinking these girls have shown absolutely no tolerance for piggish behavior. Their friends can't be too bad...I hope.

Saturday, March 20, 2010

My New Blog with Jill

I wanted to give a plug for my new blog Sex and the Sissy which I will be doing with my girlfriend Jill. The blog will be flirtier and lighter than either of our individual blogs and we'll be writing about the things that interest us most like guys and shoes and parties. We'll also have sissy advice and it'll be a great place to ask us both a question at the same time. I'm currently working on an article that should be up soon:

Sex and the Sissy

I have a few questions to answer from the blog:

"are you saying that the feeling of your skirt brushing against your stocking-clad legs does not give you a frisson of sexual excitement? I would be most surprised if it did not...Please let me know. You have lovely, shapely legs by the way." -- Sissy Isobel

I do know what you mean, but they are such a bother and so uncomfortable sometimes. If I was sexually excited by wearing pantyhose, I'd be walking around aroused 24/7. Thank you for the compliment on my legs.

"is that your real hair cindy? its soooooooo girly? i'm surprised you can ever pass as a guy?"--Mandy

I did not have real long hair when this thing started. Maybe a bit long for a guy, but certainly not feminine length. I have several very high quality wigs that I wear. The girls keep telling Jill and I that over Summer, we can go together once a week for new hairstyles, but I don't really have enough hair yet. Jill does have passively feminine hair without a wig now, but wears one for more exciting styles.

"Cindy, congratulations on looking so cute, you have come a long way in such a short time. Could you please expand on two of the comments you make?
1)....is pantyhose going to matter that much or do you face the consequences?
2) I have resisted at times, but they're always prepared for it.
What are the consequences you mention and how are the girls prepared?
On a related note, if your at college do you have a room mate (if so what's their take on things) or are you lucky enough to have a place of your own?
On the bright side, you do look cute in your new clothes and at least you have great girl friends.
:-)"--anonymous

1. It does matter, but I can't win so they go on in the morning.
2. The biggest threat is public exposure and they have more than enough. They can completely embarrass and humiliate me if they so choose, but there are also enough of them to simply overpower me. Both Jill and I have been threated with being tied up to a statue in the middle of campus in just our lingerie and heels.
3. I am lucky enough to live on my own, but it is still difficult to be undetected. In some ways, the summer apartment with Jill sounds like it would simplify my life a great deal.

Monday, March 15, 2010

Sorry I Got Behind

I'm sorry that I haven't updated in awhile, but I got hopelessly behind on some of the questions and this weekend was rather busy. I know that you heard about my makeup misadventures which are most notable because I could have gone out with my friends instead. I also had a major shopping trip in my week and I'm starting to see my closet fill up with dresses, tops, and skirts the same way that my underwear drawer filled up with bras, panties, and hose. I've heard a few people say that I must love this or I would have stopped it, but it all happens so fast. You're already wearing panties, is pantyhose going to matter that much or do you face the consequences? What difference will adding a bra make? It beats the alternative. The next thing you know, you're completely and unmistakably feminine. I don't claim to have had no choice in the matter whatsoever as much as the alternative has usually been much more attractive then resisting. I have resisted at times, but they're always prepared for it.

Wednesday, March 10, 2010

Bra Day

Today was bra day and no this isn't how I looked going to class. Even though the thermometer edged 50, I was still able to wear a light jacket and a heavy shirt and keep the light blue front clasp bra hidden. I didn't have any say in what bra I wore, but they didn't go out of the way to pick a tough one. I was very conscious of sitting in class and wearing a bra and matching panties as well as pantyhose. As each item has been added, I've felt more and more trapped. Everybody seemed to snap my bra at some time or another. Heather kept tracing it on my back with her pen cap. It was a pretty exhausting day and tomorrow it'll be another bra and another difficult day.

Sunday, March 7, 2010

Makeup and Bras

It has been a tough tough weekend. I've had three trips out shopping and I'm still trying to get used to the rather realistic breasts and bra I'm now sporting. Come Wednesday I'm going to have to wear an unstuffed bra under my male clothes. I'm not really well endowed. They made Jill a C cup, but decided I'd look fine as a B. B is still very noticeable.

This morning Amanda was over at 8AM for 2 hours of makeup practice. She calls it tutoring, but she mostly just says, "no" and tells me to do it over. She fixed my makeup before she left and I'm now stuck dressed like a school girl until one of them returns and gives me permission to change. Heels have been a huge problem for me. They keep telling me that I'm shuffing like a guy, How do I make them see that I am a guy?

After this weekend, my closet has dresses and my drawers have lingerie. I should not have let things get this far.

Thursday, March 4, 2010

Shopping List

Tomorrow is the big shopping trip after class. I've been advised that I have a choice between going to the mall dressed as a girl and going to the mall dressed as a guy and then having to try on dresses and high heels. I don't know which one is going to be less humiliating. I was told today that they were sure I would be totally embarrassed today, but that I could control how much by cooperating. I do need to ask, what you would like to see me add to my shopping list.

Cindy,I think both you and Jill are beautiful. How ofen do you girls "get" together?

They've been making us pose and model together a lot this week. They've told us both that they have plans for us and if one of us screws up, we'll both be in trouble.

Wednesday, March 3, 2010

It's Happening So Fast

Today, I had to show up for class in pantyhose. 10 minutes into the lecture, Jill brushed her hand up and down my leg to check. There was a lot of note passing in class today. This weekend they intend to take me shopping. I feel like such an idiot to be trapped this way and I keep digging myself deeper and deeper. I've also been instructed that we're going to need to find me some breast forms so that my clothes will hang more naturally. Onto the questions:

Hello Cindy, You don't seem to happy being able to spend time with 4 beautiful girls, who seem to be hard working bright and very helpful and supportive of you? I'd have thought it would be great spending time with them and Jill? In your first post you said "I've been in panties all week and I had to purchase most of them myself." where did you purchase them and what styles fabrics and colors did you decide on?

This is not something I would ever choose for myself. Walking in heels and pantyhose and trying to do everything perfectly feminine for their satisfaction isn't a lot of fun. I bought my panties at Target. They're simple cotton panties. I bought 3 packs to make things easier.

Have you started to wear long night gowns or short baby dolls yet? Once you start, you'll never want to stop!

I have not. I'm sleeping in just my panties.

Cindy, you just look hotter every time I see you. So, how do you feel knowing that guys, and gurls like me, are looking at you thinking what a hot sissy you make?

I really try not to think about that. I'm not a big fan of guys checking me out.

Cindy, you look so hot dressed as a ballerina, and your smile is so cute. I think it was nice of Sheila to teach you to dance but I'm not sure why you say that "The girls have come up with some exceedingly humiliating things to do" why would teaching a pretty ballerina to dance be humiliating?

Oh come on. You can see why wearing a tutu and dancing like a ballerina is humiliating for most guys I would hope.

Hi Cindy,
I really love your pictures, you look so beautifull all girled up. Where can we find those 50 pictures? I'd love to see all of them

Gradually the good pics will make their way onto here. They're also putting together a website to replace the one that was up. The ones online are naturally the best ones.

Tuesday, March 2, 2010

Trapped

There are a lot of questions that you have left me to answer, but I really need to get to class so I'll have to wait until later. In the meantime, I feel extremely trapped. The girlshave come up with some exceedingly humiliating things to do and if I refuse, the result is that I wind up even more humiliated. Last night, Sheila decided to teach me how to dance in heels and when I objected she told me I could try a different type of dancing that didn't involve heels. I think the picture of me looking like a ballerina is the hardest one to live down yet. There is so much that I am expected to learn.

Monday, March 1, 2010

Questions


Anonymous said...

Hello Cindy, (thats a nice name)your blog sounds interesting to say the least, especially where you say that you have posed for at least 50 pictures?
What would you say were your top three and would it be possible to post them?
I hope you update things on a regular basis'

The three up top are the top 3 that I have posed for so far that I have. I don't have all the pictures I've posed for.
Anonymous said...

Hi my name is Stephanie and ive been a cross dresser all my life and I love it. I think you make a very cute girl. I have a question for you.
Do you like the feel of girls cloths on you and do you like looking like a girl? xoxo steph

Sorry, but I don't like the feel of girls clothes and I definitely don't like how I look.
Anonymous said...

Hi Cindy,

I am really looking forward to reading your blog and wanted to ask you what you most enjoy about your transformation into a really, really cute sissy.

Love,

sissy isobel xx

I really haven't enjoyed any of it. I have cooperated because I don't have a choice, but that's not the same thing.

Sunday, February 28, 2010

Hello

I really don't even know what to say about what's going on. This week I've been in panties all week and I had to purchase most of them myself. This weekend I got pantyhose and I'm supposed to wear them next week over completely clean shaven legs. I've posed for at least 50 pictures in different outfits and different locations. It all started because I flirted with the wrong girls. One of them wasn't even a girl. Anyway, I'm supposed to write a blog detailing my transformation. I really don't even like that word. I'll answer any questions that are not X rated.