Sissy Roommate -- Part 2 -- The First Time

As I said, I am Tank's full-time sissy girlfriend now.  I wear only girl clothes and make-up and I keep my hair long and in a very feminine style. I diet to stay super skinny.  I slather my body with creams and lotions to keep my skin soft.  I do this all to please Tank.  I haven't seen Tank all summer and he should be arriving any minute. Here are some photos Tank took of me last spring. He likes it when I wear really short skirts.

But I wasn't always a girlish sissy living only to serve a demanding, strong alpha-male. My life changed completely that first day that I met him.

"Come over here," Tank said, without even bothering to ask my name.  "I have a cramp in my leg.  I need you to massage it for me."  Tank pulled off the sweat pants he had been wearing, revealing a thin pair of nylon gym shorts.

I did not want to do what Tank was asking.  "I don't know anything about massages or..." I started to explain.

"Just do it now!" he demanded, pointing to his thigh.


I don't know why, but I complied with his order.  I figured he was an important athlete and that I should try to help him out if I could.  I knelt by his bed and started rubbing his thigh.

"Mmm.  Yeah.  That's good.  Rub harder.  Yeah," he said.  I was pleased that I was doing it right.  "You're hands are so soft.  Like a girl's."  I felt embarrassed when he said that but I kept on rubbing his thigh.

"Now jerk me off," Tank said as if it were the most natural request in the world. I was completely shocked when he said that.  I pulled away from him and said I wouldn't do that.  "Yes you will," he insisted.  With one hand he yanked down his shorts and with the other he grabbed my wrist and forced my hand on his enormous dick.  "Do it," he commanded, keeping his hand firmly wrapped around my wrist.  I was really scared and no match for this mountain of a man.  I wrapped my fingers around his huge cock and started stroking him, pumping him.  "Yeah, bitch! That's it!"  His breathing got more rapid and his dick started swelling.

"You know," he said, "You sort of look like a girl.  You got long hair and no muscles.  Yeah, I think we're going to pretend that you really are a girl."  He was really panting now.

"Use your mouth, bitch" he ordered.  No way I was going to that, but Tank grabbed hold of my hair and forced my head to his crotch.  I sealed my lips tightly closed, but with his other hand, Tank pinched my nose so I couldn't breathe. "Open wide, slut," he said with a laugh. As I opened my mouth to gasp for air, Tank jammed his dick into my mouth.  With both of his hands now tightly holding my head in place, I had no ability to move or fight back.  And in an instant, Tank's cock exploded, filling my mouth with spurt after spurt of his hot, sticky cum.

When he was done with me, he roughly shoved me away.  "Next time, wear a dress and some make-up or something so it won't feel so gay."

"What the fuck," was all I could think, as I pulled myself up from the floor and ran out of the room. 

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!

 

A Christmastime Sissy - Part 1

Well, Christmastime is almost here.  And I thought you would enjoy hearing a Christmas story about my sissy husband.  I've included a few Christmas photos of my husband -- that's him with the long curly hair, the pretty blue dress and the beautiful smile.

My husband has been a crossdressing sissy throughout his entire life.  I knew he was into dressing up in ladies clothes before we were married -- and I didn't mind -- really.  But over the first few years of our marriage, I began to understand just how deep his feminine needs ran.                                                           I had no problem with him dressing up as "Suzanne" on the weekends.  I even went out to bars with him a couple of times when he was all dolled up.  And when he was dressed up as Suzanne, he really enjoyed acting like the housewife in our relationship.  And do you think I was going to complain that he did almost all of the cleaning and cooking just because he was wearing a dress, a frilly apron and heels?  No way!  I'm no fool.  I had a great thing going.

But over time I began to understand that I was seeing just the tip of the sissy iceberg.  The part that I couldn't see, that was lurking beneath the surface of the water, was an unstoppable need for my sissy husband to push the boundaries, to come as close to experiencing life as a real woman as he could.  And that of course led to...men!                                                                                   I knew that Suzanne was spending a lot of time each day on the internet -- but I didn't know what he/she was doing.  As it turned out, Suzanne was meeting men who were looking for "relationships" with feminine, pretty, submissive sissies, just like my husband.  It took some time, but eventually I got onto Suzanne's email and blogs -- and let me tell you -- I nearly fell down.  There were dozens of men -- literally dozens! -- flirting with my husband, sharing photos, and asking Suzanne for dates -- and more!

I was surprised to learn how many men out there are really into sissies.  But I wasn't really surprised that Suzanne had caught their eye.  As a man, my husband is rather unassuming.  But when all dolled up as Suzanne, he is very attractive, I have to admit.  The few times we went out together as girls, he always got a lot of attention, compliments and free drinks from the men floating around the bar.                                                                                                                                                               One of Suzanne's online suitors turned out to be a very successful lawyer named Paul who was separated from his wife.  Paul lived in a town about 20 minutes away from where we lived.  By scrolling through Suzanne's email, I realized that they had been seeing each other -- very carefully and infrequently -- for several months.  That sneaky Suzanne!  I had no idea until I read his/her email.

Anyway, around Thanksgiving, I confronted my husband with what I had found.  He tried to deny it at first but he quickly surrendered since there was just too much evidence against him.  But once he admitted to what he had been up to, I reassured him.  I told him I didn't like him being unfaithful.  But because I understood what a complete sissy he was, being unfaithful with another man wasn't as bad as being unfaithful with another woman.                                                                            I told him that I was going to give Suzanne a very special Christmas gift: a two-month "hall pass."  Suzanne could do whatever she wanted -- anything at all -- for the next two months, until the end of January.  But I wanted her to get it out of her system and then I expected my husband to come back to me.  My husband agreed to my proposal with tears of gratitude.  

"Well, girl," I said to him. "Get busy.  Because on February 1, your hall pass expires. So go be a woman, in whatever way you need to."                                                                                                                                                                                           I'm sure that Suzanne's boyfriend, Paul, wasn't going to believe his good luck.  Instead of stealthily seeing Suzanne on a few rare occasions, he was going to get to have as much of Suzanne as he could handle for two whole months.                                                            

And that brings us to Christmas.  As you can see in the photos, these two love birds thoroughly enjoyed their time together.  Just look how pretty and happy my Suzanne looks.  And her boyfriend is actually a very nice man, fairly wealthy and not bad looking at all.  Suzanne really scored a winner.                                                 But as the days in January flew by, I was left with so many doubts.  Looking at these Christmas photos showed me just how much Suzanne enjoyed acting as the wife/girlfriend to a real man.  He/she seemed freer and happier than I can remember him being for a long time. I didn't want to lose my husband that I love so much.  But I also didn't want to take away from him an experience and a lifestyle that was clearly so fulfilling for him. So around the middle of January, after having given it much thought, I decided to have a conversation with Suzanne.  We met for lunch at a local cafe -- something we had been doing once a week throughout December and January.  I decided that I was going to leave it up to Suzanne to chose to either come home to me or to stay with his boyfriend.  

Well, as we sat down for lunch, and as I was about to start my prepared speech, Suzanne surprised me and started speaking.  "Honey," she started, "I have something important to discuss with you..."

 

Taking my Sissy Husband on Vacation

My husband and I are having the most wonderful vacation together.  That's me in the photo on the left, the brunette in the black dress.  But that's not my husband in the photo! That's my new vacation boyfriend, Jerry.  I met Jerry earlier this week at the resort bar.  You see my husband is not a real man like Jerry.  My husband is a feminine, submissive sissy. 

That's my sissy husband in this photo -- the pretty blonde "lady" in the sexy gold dress.  His real name is Martin, but he is living only as "Tina" this week while we are on vacation.  And as you can see, Tina landed a handsome new vacation boyfriend too! His name is Darren.

My Tina is very, very good at passing as a woman.  He works hard at keeping his body slender through a strict diet and body-sculpting exercises.  He keeps his hair long all the time, but dyed it and had it styled especially for this trip.

Don't you think they make a cute couple?  Darren is everything that my Martin/Tina isn't. He's strong, confident and decisive.  A real Alpha male! I love seeing Tina with Darren. It seems like Tina doesn't have a single idea of his own when he's with his hunky new boyfriend -- Tina seems only capable of agreeing with whatever Darren says and whatever Darren wants to do.

I love seeing how Tina behaves when he's with a real man!  That's why I planned this vacation to a singles resort.  Although we have been out together as two women many times before -- to restaurants and bars and so on -- we had never taken a week-long vacation like this before.  For Tina -- and for me -- it is a wild, new experience!

I know my sissy husband enjoys his time as Tina.  I know that his need to express him feminine side is far too powerful for him to resist.  And being in the arms of a strong, masculine man is so exciting for him, throwing his feminine feelings into overdrive. But tricking a man to believe that you are a real woman when you are not is playing with fire!  And Tina knows this. Each moment he spends with an unsuspecting man fills Tina with equal parts excitement -- and fear that his secret will be revealed.

Tina and Darren have been an item for three days now -- and we have three days left in our vacation.  Can Tina keep up the act for the rest of our vacation without letting Darren find out the truth?  I certainly hope so.  I expect that Darren would be furious beyond belief if he learned that the woman he was falling for was really a man.

So how does Tina manage to keep his secret? Well, the first night was easy --  just some flirting and a little pawing at the resort bar, with a brief good night kiss at the end of the evening.  By day 2, things were heating up, with some heavy making out during the day and a hand job in Darren's room at the end of the evening.  (His cock is enormous, Tina reports!) 

Today is day 3 of their steamy relationship.  I caught Tina and Darren making out like crazy earlier today -- including in the swimming pool!  Now we are all dressed up for a double date together.  First we'll have some Happy Hour cocktails, then a romantic, candlelit dinner together, followed by dancing at the outdoor bar until late. It's what happens after that that has Tina very nervous.

"You better hope he likes blow jobs!" I told Tina. "And I hope you are really good at giving them.  Because he is going to expect to get some serious action from you. And since he can't fuck you, you better find some other way to keep him interested." Tina has practiced giving blow jobs on the strap-on dildo I sometimes use on Tina's backside.  But Tina has never had a real cock in his mouth -- or down his throat.

 

Of course, I've been fucking my new vacation boyfriend every chance I get this week.  We run off to his room a couple of times during the day and of course in the evening. He is amazing in bed! And I always give Tina a detailed report on my sexual encounters with Jerry.

I really hope that Tina -- and his pretty mouth -- can keep Darren satisfied and unaware of the truth. They make such a cute couple and Darren really seems rather smitten by Tina. And I can tell Tina is really falling for Darren.

Keep your fingers crossed that Tina can really pull it off. With a little luck -- and a lot of sucking -- Tina just might come home with wonderful memories of his romantic vacation with Darren -- and a tummy full of Darren's hot, sticky cum!

 

Mommy's Pajama Sissy -- Part 12 -- The Conclusion

It turns out that Jimmy told Tammy that, as Captain of the football team, he was expected to "share" his girlfriend with some of the other seniors who were on the team.  This is what I overheard Tammy talking about on the phone.  Well, I couldn't believe what I was hearing, but it seems like my sweet, innocent Tammy was going to listen to whatever Jimmy said -- and do whatever Jimmy asked.

The very next day, I heard that Jimmy and Tammy went to the beach -- along with Jimmy's teammate Marcus.  Tammy didn't share any of the details of what happened at the beach but he seemed completely fine with whatever did happen.  I guess Tammy enjoyed the extra attention of two boys instead of just one.  

I soon had the impression that Tammy's dates with Jimmy usually included one -- or more! -- of Jimmy's football buddies.  I began to become concerned that Tammy was letting himself get caught up in something that wasn't very healthy for a young lady like Tammy.  But as unhappy as I was that Tammy was being "shared" among the players on the football team, I soon learned that the situation was perhaps even much more worrisome than I knew.

Tammy had been very open with me about his early experiences with Jimmy, but as the summer wore on, Tammy became much less willing to fill me in on the details of what he was doing.  I started checking his phone when I could just to get an idea of what he was up to.  So you can imagine my shock when I found these photos on his phone.  Because that's not Jimmy that Tammy is kissing.  That's Jimmy's Uncle Mike who owns the garage where Jimmy works!  Mike is in his mid-40's and shouldn't be romancing an innocent teenager like my Tammy!

And not only was Jimmy "sharing" Tammy with his Uncle Mike -- but apparently, Uncle Mike was "sharing" Tammy with his friends too!  The photos on Tammy's phone weren't very clear so maybe I'm not exactly sure what I'm looking at. Maybe you can figure out what's really happening here...

Oh dear! Perhaps this is all my fault!  It was just so much fun when we started wearing cute pajamas and nightgowns together  I could never have imagined that it would lead to this.