Sissy Roommate -- Part 1 -- What I Look Like Now

It's the start of the college year.  I would be a junior now except that I dropped out after the end of last year.  But my boyfriend, Tank, is starting his junior year. I didn't think I would be able to take care of him properly and go to classes at the same time so I dropped out. 

I have been working for days getting our off-campus apartment ready before Tank arrives later this afternoon.  I bought new sheets and towels for him, new pots and pans for our kitchen, even some nice pictures to hang on the walls.  And I scrubbed every inch of the place so it would be sparkling clean when Tank arrives.  Of course I had to spend most of the money I earned waiting tables this summer, but it will all be worth it if Tank is happy with how our apartment looks -- and if he is happy with me.  And I spent the rest of my money on some pretty new clothes and shoes.  I don't have a single dollar left -- but that's OK because Tank has tons of money.

I finished all the apartment chores about an hour ago. That left me time to get cleaned up, do my make-up and put on one of my pretty new outfits before Tank is scheduled to arrive.  Do you like how I look?  I bought this dress over the summer and I think it is sweet and sexy at the same time.  And I think Tank will go crazy when he sees my over-the-knee socks and platform sandals.  What do you think?  After being apart all summer, I really hope Tank likes what he sees when he arrives.  I don't like to disappoint him.                                                                     Maybe I have gotten ahead of myself. Let me fill you in on some things.  First of all, Tank and I have been roommates since the beginning of last year. Tank is a superstar football player - that's where his nickname comes from.  Oh, and one more thing.  I'm not really a girl.  I'm Tank's sissy. 

It all started last September, at the beginning of my Sophomore year.  I had a really great dorm room -- a double room with its own bathroom -- but I had no roommate.  The Housing Office warned me that at some point I would be assigned a roommate and that my "single" was not a permanent thing.  Well, about one week into the semester, I came back to my room after dinner and there was this enormous guy in my room -- 6' 8" at least.  Everything about him was huge -- his shoulders, his neck, his biceps.  With him was a little man in a suit who was talking a mile a minute. "Well, Tank," the man said to him, "Since your decision to come to State U was so sudden, this is the best room we have for you. Of course, we'd rather have you down in the Athletes' Village by the gym, but that's all full right now.  But on behalf of the administration, the university is DELIGHTED to have you join us! I hope you can make do with this housing...situation until we can get you a more appropriate room." The little man seemed to be referring to me as part of the lousy rooming situation that Tank was going to have to tolerate.

"I'll make it work," Tank replied, his voice, a deep, rumbling baritone that sounded like distant thunder.

"That's swell, Tank!  Just swell! Let me know if there is anything we can do for you," the little man said as he handed Tank his card -- and an envelope that I would later learn was stuffed with cash.  "And good luck with the season. We hear that you just might break a lot of school records and even take us to a Bowl Game this year!  And let me know if you need anything. We're here for whatever you need. Just ask." With that the little man excused himself.  

The two of us were now alone in our room.  Tank plopped down on his bed and looked over to me.  I thought he was going to start a conversation, but instead just said, "Come over here."

A Christmastime Sissy - Part 2

As I explained in my previous post, my husband, "Suzanne," is a crossdressing sissy.  I love him very much and I decided to give him the greatest gift of all at Christmas -- the freedom to be exactly who he wanted to be.  Suzanne had a "hall pass" for the months of December and January to be the woman he always dreamed of being -- and to do it with his handsome boyfriend, Paul.

When January was halfway over, I was beginning to realize just how happy Suzanne had been living out his fantasy of being a woman.  I mean, just look at these photos.  Suzanne looks so at peace, so fulfilled.  And while I wanted to get my husband back, I also felt I had to duty to help Suzanne achieve his/her own destiny.

At the cafe where we were having lunch together, I was about to tell Suzanne that he could continue living as a woman with Paul, if that's what he really wanted.  Instead, Suzanne surprised me with an offer of his own.

"Honey," he said, "You know that I have been enjoying my time with Paul over the past six weeks.  And you know that I also love you so very much."  I nodded in agreement, a few tears started to well up in my eyes.

"Well, Paul came up with an interesting idea.  Why don't the three of us...get together.  You know, as a "Throuple" as the kids say.  He's a very nice man and I'm sure you find him attractive." I couldn't respond.  I was stunned by what I was hearing.

"But why not give it a try.  Who says we have to chose between being together and me living as Suzanne?  I know it might sound crazy at first, but please just think about it.  I think it could be wonderful.  I love being Suzanne.  And I love you.  And I love the experience of being romanced and cared for by a real man.  Paul would do the same for you.  If you let him."

I was speechless. But looking across the table at my beautiful Suzanne -- his hair and make-up just so perfect.  His lovely smile and his pretty eyes.  His feminine gestures and lilting, gentle voice.  I felt an odd desire for him that I hadn't ever felt before.  He was just so...ladylike and elegant.  And then add in all the talk of having me get romantically involved with that handsome man.  My pulse starting racing and my panties started to get damp.

"Please say you'll think about," Suzanne begged.  "I think the three of us could have a wonderful life together."

Well, dear reader, that all happened five years ago.  I did agree to Paul and Suzanne's offer.  And our lives have become an exciting, magical journey.  Over the course of those five years, so much has happened: Paul's divorce was finalized, I sold my house and we all moved in together in Paul's lovely home, Suzanne started hormones and has become more womanly and more beautiful each day.  And while Suzanne and I are still legally married to each other, we even had a commitment ceremony where the three of us effectively "married" each other.

Suzanne is delighted to take care of almost all the chores around the house.  She prepares lovely meals for us, does all the laundry and tidying.  She fusses over Paul and me like some idealized housewife from the past.

And of course, there is the sex.  I hadn't realized how much I missed being in the arms of a real man.  And believe me, Paul is quite the stud.  He is tall and strong and very muscular.  And his cock is massive!  My own husband couldn't ever give me that kind of experience -- even when he wasn't dressed up like a girl.

Most nights the three of us climb into our king size bed together.  Suzanne and I usually wear matching nightgowns and we lay on either side of Paul.  As we snuggle up against his naked body, he wraps his big arms around us and pulls us close, our heads laying on his strong chest.  Love comes in all combinations -- sometimes all three of us at once, often any combination of the two of us.  I never feel any jealousy; my needs are fully satisfied and I am delighted when Paul and Suzanne have their intimate moments together. (And sometimes I like to watch!)

Paul often travels for work. Sometimes, one or both of us will go with him.  But most often we both stay behind, making that a special time for just the two of us.  I don't look at Suzanne as my husband any more -- I look at him as my beautiful, feminine lover and best friend.  And with that perspective, I delight in our lovemaking when it is just the two of us.  I love Suzanne's soft and smooth skin, her skinny delicate frame, her tiny adorable dick, and her extremely talented tongue.

So that is my Christmastime sissy story.  Maybe I should say it was my own Christmas miracle.

I hope all of your sissy dreams come true this Christmastime!

 

My Sissy Neighbor -- The Conclusion: Honeymoon

A lot of time has passed since my last post.  And a lot has happened for my sissy sister, Anita.  The biggest news is that Anita got married!                                                                                                                                                     A very handsome, divorced lawyer (his name is Jackson) was looking to buy a home and Anita became his realtor.  One thing led to another, and before long, they were dating.  Six months ago,  Jackson proposed to Anita, giving her the biggest, most beautiful diamond ring I have ever seen!  Of course Anita said yes!  Here are some lovely photos from their "Engagement Shoot."  Isn't Anita exquisite?

 The wedding was intimate and lovely. I was the Maid of Honor and of course mom was the Mother of the Bride!  And, as you would expect, Anita was the most beautiful bride ever!!!





Here are some photos from their honeymoon in Hawaii that Anita posted.  Here she is in a lovely black and white print dress that I helped her pick out.  Anita loves how this dress shows off her every curve.  Of course, she isn't wearing a bra underneath a dress like this.  I'm sure that Jackson is so pleased to have snagged the gorgeous Anita to be his bride and to have this lovely creature hanging on his big strong arm as they stroll around this tropical paradise. And Anita told me all about the hot sex they had during their honeymoon.  Apparently, Jackson has quite the sexual appetite -- and the equipment to go with it!  Anita said their honeymoon was a continuous round of eating, drinking, dancing, swimming and fucking!   

And here's Anita lounging by the pool. She loves putting her crazy curves on display in her sexy swimsuits. She knows that every guy around the pool can't take their eyes off of her -- even when their wives and girlfriends are right there!  Just check out Anita in her blue one-piece.  It can barely contain her giant boobs!  I love it! 

I am so happy that my sissy neighbor has found her new life as a successful business woman, a beautiful, voluptuous lady, and a devoted and loving wife of a handsome man. It has been a wonderful experience for me watching this amazing transformation and journey. And through it all I guess I lost a sissy neighbor and gained a sister. 

My Sissy Neighbor -- Part 11: Some BIG Changes

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My Sissy Neighbor -- part 10: Anita's Evolution

Anita was now living and working full-time as a woman.  His name was legally "Anita", and socially he was becoming more female every day.  Because he is so beautiful and charming, men are always asking him out for dates.  Anita sometimes accepts, but has to limit the intimacy because he is not at all what his suitors think he is.  But all of that is beginning to change!  Anita told my mom that he wants to become Anita permanently and physically, meaning that he decided to start hormone treatments and to start planning for surgery to become a real woman!  Isn't that exciting!

These are some photos mom took of Anita before going out on one of his recent dates.  In these photos, Anita has been on hormones for just a couple of months.  But doesn't he look different already?  I mean, he was already beautiful, but somehow the hormones are having some kind of effect on him in ways I can't explain.  I think he is incredibly beautiful.

Tonight, Anita is going to a charity ball on the arm of a handsome young (and successful!) banker who has taken quite an interest in our Anita.  Anita's gown is long and sparkly.  It clings to his every curve.  And soon enough, those curves are going to be Anita's own body, not carefully placed silicone pads.  Every eye at the ball will be on Anita, I'm sure.

Anita hasn't yet had surgery, but he has become a real woman as far as I'm concerned. "He" is really now a "she."

My Sissy Neighbor -- Part 9: The Real Anita

Over the next several months, Anita became more than just a pretty and competent assistant to my mom in her real estate business.  Anita was proving to be a valued partner to my mom.  Together they increased mom's book of business by 100%!                                                                                             Anita was living and working full-time now as Anita, a very attractive, young professional woman.  Here are some photos of Anita in full realtor-mode.  Look how poised and confident and relaxed he looks.  He was meant for this life and this career!

As for the matter of his real estate license, well obviously he aced the exam with no issue.  But there was still the matter of his name.  His realtor's license had to be in his legal name.  So mom took Anita down to the court house and helped him with the paper work necessary to officially change his name from Andrew to Anita.  While they were at the court house, Anita asked mom, "Is it OK if I change my last name too?"  Mom replied that he could do that if he wanted to.  "I want to have the last name 'Campbell'", Anita said.  Mom was shocked.  Campbell was our last name.  "You are my real family," Anita explained to mom.  "And besides, since I'm supposed to be your niece, wouldn't it make sense that we might have the same last name?"  Mom was so happy and so proud, that she started crying in the court house.                                                                                                                                                      "I'm so happy," mom said.  "And I don't think of you as my niece.  I think of you as my second daughter."  That made Anita cry when she said that.

Of course, by now I was away at college, so I missed mom and Anita a lot.  But I was able to come home every few weeks.  They were both always happy to see me.  When I would come home, Anita and I would typically sleep together in my bedroom -- slumber party!  I don't know if mom knew we were having sex, but I didn't care.  I needed to spend every possible minute with my beautiful Anita.

Anita was also getting a lot of romantic attention when I was away.  As I said, male -- and sometimes female -- clients were always hitting on him at work.  Mom had a strict rule about not socializing with "active clients."  But after a deal was done, mom said that Anita could socialize or date anybody he wanted.  Well I know Anita went on a lot of first and second dates.  But he had to avoid letting anything get to serious because...well it's obvious why.

My Sissy Neighbor -- Part 8: Transition to New Life

Mom and I did our best to help Anita settle down after his horrible ordeal.  Mom wanted him to go to the police, but I knew he wouldn't agree to that.

"Well, at least you are NEVER going back to that awful club."

"But I have to!" Anita wailed.  "I need the job if I ever want to move out of my house!  I can't stay there anymore.  Things are so bad with all the yelling and drinking and..." Anita took a deep breath and continued.  "I think my dad is beginning to figure out that I'm not exactly the man he thinks I should be.  And if he ever figures out about Anita, hell kill me.  I mean it!"

He continued, "I've been saving up my money so I can move out of the house.  Maybe I will move to California."

Mom and I stared at each other for a moment and then said -- in unison, "Just move in with us!"

Anita looked confused for a moment and then said, "But I can't move in here.  I don't want my parents to know I live just next door.  That won't fix anything."

Mom spelled it out for him.  "Move in with us as Anita.  Let your parents think that Andy has gone to California or Timbuktu or where ever.  Graduation is in just a few weeks.  Stick it out until then.  Then say 'so long' to your folks, pack up your car and start the long drive -- to the house next door!"  Mom seemed very pleased with her solution.                                                                                                         "But, my parents will recognize my car," Anita protested."Sell it.  Get a new one with all the money you saved up." Mom replied.                                                                                                                                                      "But what would I do all day as Anita?  I've never lived full time as Anita before," he noted.

"Well..." mother replied, "I could use help with my real estate business,  Things are really booming.  And my own daughter has no interest in real estate." She was referring to me, of course -- and it was true. She continued, "Besides, she's heading off to college in just a couple of months."                                                                                            We talked about it for a long time into the evening and Anita finally gave in to mom's proposal.  A lot of things happened over the next few weeks. Let me fill you in:

Andy graduated and told his shitty parents that he was moving out.  He dropped his few belongings at our house and then traded in his awful car for a really nice used Audi A4 sedan.  It was definitely the car Anita belonged in.                                                                                                     Anita started helping mom out with her business, handling some simple phone calls, making appointments, sometimes signing-in people to open houses.  Here are some photos of Anita that mom took during Anita's first few days showing houses.  Mom noticed right away that Anita was a natural at this.  Anita can talk to anyone -- a skill he honed at the club, no doubt.  And of course, being gorgeous didn't hurt either -- especially with the male customers.  But mom noticed even the female clients seemed intrigued by and drawn to him.  Mom started giving Anita more and more responsibility.  And by the time I went off to college in late August, Anita was studying for his realtor's license.

And for me, the best part of the summer was having Anita living with us full-time!  We kept it quiet from mom, but we found lots of time for our little make-out and hand-job sessions. One day Anita asked me to show him how to eat pussy.  I was more than happy to let him practice on me!  And he was a natural!  I have never cum so hard or so many times in my life. It was such a turn on to see that beautiful blonde hair of his between my thighs; feeling those full, lip-stick coated lips and his very talented tongue go to town on my pussy.  It was the best summer of my life!                                                                                                                   "Anita," mom said one evening before they sat down to dinner.  "We need to talk."  Anita was concerned by mom's unusually serious tone.  "Anita, you are doing a great job helping me with the real estate business.  I am so impressed by how mature and professional you are.  And I know you are going to ace the real estate license exam."   Mom took a deep breath.  "But you can't be a realtor and sell real estate under a false name.  You have to use a real name -- on your license, on your business cards, everything."                                                                                                                           Anita turned pale.  His dreamy new life as beautiful Anita, as a young professional woman starting out on a real career, seemed to have crashed.  "But I can't live like this and call myself Andrew for goodness sake."                                                                                                          

"Of course not," replied mom. "So maybe this is the right time for you to say good-bye to Andrew and become Anita.  For real.  Legally, and if you want, surgically." Oddly, this suggestion came as a surprise to Anita.  Anita sat in silence as he thought about what mom had suggested.  And then mom added brightly, "And then you can be my niece for real!"