Sissy Marries Cheerleader

When I was a high school freshman, there was this girl.  She was one of the Varsity cheerleader co-captains.  She was also a senior.  But more importantly, she was a cheerleader.  And I had a major crush on her.

As you can imagine, with her being a senior, and one of the head cheerleaders, and me being a freshman, the chances were that I had no chance with her.  And you'd be correct.  I didn't.  She didn't even know I existed - literally.  I am 100% certain of that statement.  But, that she didn't know I existed, and that I would never get up the nerve to do or say anything to cause her to notice me, didn't stop me from fantasizing about her endlessly, and doing everything in my power to be near her and her orbit.  I went to all of our school's football and basketball games - home and away - always sitting in the bleachers near the middle of the cheer line, where she and her pretty co-captain were situated.  I followed her wherever a Varsity team went my freshman year.  I didn't have a girlfriend my own age.  Shoot!  I was too afraid to approach any girl - much less this senior cheerleader.  And I never did.  She graduated, and I transferred from that high school the next year, without ever even speaking to her.  She was, as we've heard it said, the most popular girl in school.

So, now we go back to where I left off at my last post.  My first wife left me for another man, or, as I've acknowledged, a man.  We had to go through the required legal separation before we could get divorced.  We had no children, and I saw no reason to battle her, since she had her mind made up, so I simply watched her walk away into the arms of this man she'd found who could satisfy her.   I didn't date during my separation.  At all.  No one.  I was pretty despondent over losing my wife, especially knowing deep down inside why it happened.  Friends were trying to set me up like crazy.  I was viewed as a very eligible bachelor.  I was a successful and respected attorney.  I was (am) a pretty good looking guy.  But I resisted my friends' efforts to get me to go on dates. 

If it hasn't yet, this is where my story gets interesting.  There was this girl friend of mine who kept telling me that she had a woman I had to meet.  That we were perfect for each other!  This woman had recently been divorced by her jerk husband who'd left her for another woman, leaving her with two young children.  I resisted my friend's effort to set us up for two reasons.  One, I simply wasn't ready.  And two, I wasn't sure I wanted to get involved with a divorced woman with children.  But my friend was patient.  She told me to let her know when I was ready.  I let it go at that.  

The week after my divorce became final, I attended a Friday night after work function at a downtown Happy Hour and bumped into a guy who had been a juror on a big (by "big," I mean "huge") case I'd just won.  He and his wife approached me and he began telling me how cool the trial was, and how impressed all of the jurors were with how I controlled the courtroom.  Yeah!  That was nice to hear.  While he and I talked, his wife was checking me out.  She managed to find out that I wasn't married.  Women and their guile!  I envy it.

As we were about to say our goodbyes, she asked me if I had plans for dinner.  I'm not stupid.  I could tell she wasn't just randomly asking me to join them.  So I asked her why she asked.  She told me they had a friend who she'd like to introduce to me.  Again, I'm not stupid.   I had no idea what this woman looked like.  I wasn't accepting efforts to set me up with girls I knew were pretty.  I sure wasn't going to randomly agree to go to dinner with someone I'd never seen.  So I'm giving this juror's wife a non-committal response when guess who walks up?  I hope someone guessed it.  It was my cheerleader.  I didn't hesitate.  I turned to the juror's wife and said, and this is a verbatim quote, "Absolutely!  I'd love to join you guys for dinner."  I didn't want there to be any chance for them to back off.  

Somehow, at dinner, I got around to telling my cheerleader about my high school crush on her.  She confirmed for me that she didn't remember me at all.  Like I said.  

She seemed hesitant at first, but I could tell she liked me.  It's amazing how those three years that separated us in high school seemed like a generation of difference, but at our current age, it seemed like only weeks apart.  To shorten the story some, I'll simply say we began dating.  I liked her kids.  And they liked me.  We began seeing each other nearly every day.  

Soon, we reached the moment.  The moment when we were going to spend the night together.  I was so scared.  I really liked her.  I thought we were falling in love.  We were falling in love.  But would I be able to perform?  I knew she could.  She had been pregnant twice.  But I never had done it.  At my age, that was something no woman would understand.  Despite my fear of failure, I knew that I had to at least try, and fail, or our future would never be.  

So, one night, I let the kissing and petting go further.  That almost sounds funny - doesn't it?   For the guy to be the one who let sex escalate, rather than the other way around.  Her kids were spending the night with her parents, so she took me to her bed.  I could tell she wanted it, and was tired of me delaying making my move.  The first thing I did was something I knew that I could do.  Something I was good at.  I went down on her.  And she liked it.  A lot!  She let me know how much she liked it too.  I licked and sucked and ate her for at least an hour.  Finally, she couldn't stand it any longer.  I was amazed at how hyped she was.  I'd never seen a woman respond this way, because I was completely inexperienced.  I'd certainly never made a woman react to me like that.  

 
She was totally in charge as she pulled me on top of her and directed my penis toward her pussy.  I can still remember the moment vividly - I was so afraid that, once again, I would fail to perform, and then, before I realized what was happening, I was inside of her soft, wet pussy, and she was begging me to fuck her.  To fuck her!  To fuck her!  I couldn't believe it!  I was fucking her!  I was fucking her!   I was fucking a woman!  It was unbelievable, to be nearly twenty-eight years old, and fucking a woman for the first time in my life.  And she enjoyed it too.  No.  She loved it.  I pleased her.

We fucked all night long that first night.  As soon as I could get it up again, I fucked her.  And we began fucking like that nearly every night.  She'd been hurt so badly by her jerk ex-husband who, by the way, was the starting quarterback for our high school.  I'm not making this up.  I know it wouldn't have happened if I looked like a sissy on the outside.  But I didn't.  I'm a good looking man. And I was with the head cheerleader who'd married the quarterback, and I was pleasing the hell out of her.  

Again, to shorten the story some, we were married within six months of meeting.  At that point in my life, wearing women's underwear was the furthest thing from my mind.  All I knew was that I could have sexual intercourse with a woman.  As you can imagine, I worshiped her - the woman who helped me fuck a woman.  And so, we moved on with our wonderful life.  It was only later in our marriage that my "urges" bubbled back to the surface. And I don't think anything could have prevented them from escaping.

We're still married.   But a lot has happened since we met and married.  More on that in a post in the near future.  Oh - one more thing.  The woman my girl friend told me I had to meet?  Because we were perfect for each other?  It was my cheerleader.  Pretty cool - huh?

Read more »

That First Time

You never forget your first time

It doesn't matter what you want, now stop your whining and assume the position.

Read more »

For her Pleasure

Hubby finally gives her an orgasm

The best part about the mouth gag dildo is how she can rub her clit over his nose on the down stroke

Read more »

Exhausted Sissy Needs Stress Relief!!

I've mentioned this in an earlier post, but resurrecting and reliving my sissy journey has been more mentally and emotionally taxing than I originally anticipated.  I want to get the entire story out there, so that the many lovely people following my new blog will learn where I am today.  I can then begin sharing some of my current sissy situations.  Of course, I suppose I could sprinkle in a few of those details as I go, but I'm not.  I want to maintain some sense of suspense.  

I promise to keep pressing onward, but may need to take a few breaks from going into more of the nitty gritty sissy details.  Each post, for me, raises my stress level as I freshly consider each stage or event.  Everybody has their own way to deal with such stress.  For me, other than sports, I really enjoy baking.

And, of course, whenever I bake, I simply have to be dressed appropriately.  Otherwise, the results of my baking efforts never seem to turn out as well.  

See what I mean?  Beautiful!  Huh?  The cupcakes!  The cupcakes!  And then, of course, no cooking project is complete until the kitchen is sparkly clean at the end.

Finally, after enjoying the fruits of my labor, one last cleanup job is always a nice cherry on top of the sundae.  What sissy doesn't enjoy this cleanup duty?

There!  I feel all better now!  Next blog entry - more on my sissy journey. 

Read more »

A Virgin Bride (And Groom)

I got married between graduation from college and beginning law school.  I married my best friend's sister.  She and I had always had a thing for each other, and discovered that we were in love as I neared the end of college.  We were each pretty innocent with the opposite sex.  For her, I think it was simply that she was a "good girl."  For me, although I couldn't name it or describe it then, it was that I was afraid.  Afraid of failing to be able to "do it."  That's right.  We were both virgins when we got married.

On our wedding night, neither of us knew what to do.  My new bride, who I was a few years older than, rightly, expected me to know what to do.  Me, being the guy, and older, thought I ought to know what to do.  But the reality was, that I didn't, and so we didn't fuck the first night of our marriage.  Instead, I ended up cumming all over her, but never getting inside of her.  She was nice about it and all, but I could tell that first night she was confused about why we didn't "do it" on our wedding night.  I tried to pretend like it was okay, but inside, I was devastated.  I'd feared my inability to "perform" all along, never admitted to anyone that I was a virgin, and when I failed to perform in the clutch, I cinched it in my own mind - I couldn't "do it."  The rest of the Honeymoon wasn't any different.  We didn't "do it" the entire Honeymoon. 

I know that what I'm about to admit may be difficult to believe, but although we loved each other, and stayed together for a long time before she finally, one day, announced that she was leaving me for another guy - or, I should say, simply, a man - we never actually consummated our marriage.  I satisfied her to some extent, because I was good at giving oral, but I knew it was never really enough.  She wanted a man.  And she wasn't comfortable reciprocating with me.  So, I never was on the receiving end of a blow job.  Instead, I ended up cumming on her when we humped because I never could get it in her.  Our marriage fizzled to an end, just like my performance in bed, and we never discussed it.

When my first wife left me, I was devastated.  It wasn't just that the woman I loved left me for another man.  I knew why it really happened.  I simply wasn't man enough.  She didn't leave me for another man.  She left me for a man.  If I had been one, she wouldn't have left me for a man who could please her like a woman needs, and deserves, to be pleased.  By then, I was a full-fledged adult, and I was still a fucking virgin!  By the time she left me, I'm quite certain she wasn't one.  We were married for six years!  I was twenty-eight years old!  I worried that I would never have intercourse with a woman.  And you can imagine how fearful I was of dating new women - women who weren't childhood friends who knew and liked me - women I had to impress - and worrying how I would prove to these new women that I couldn't fuck them.  And they'd talk to other women around town about it.  Fuck!  I was a mess!

And remember what I've mentioned in an earlier post - I was a guy's guy.  I played sports.  I was competitive.  I was a trial attorney, and a very formidable one.  Other attorneys liked me and respected my tough, competitive fire in the courtroom.  But I'd never fucked a woman.  Can you imagine?  Hanging out with guys in locker rooms, always talking about fucking this girl, or that girl?  You know?  How guys talk?  And always lying about my own exploits?  As in, I had none.  It was tough.  I felt like Charlie Brown.  I wanted to ask girls out.  But I was afraid if I did, and they said yes, I'd only prove how worthless I was, rather than simply have them suspect it.  And so I spent a lot of time alone after my first marriage.  And guess what I did?  Living alone for the first time as an adult, with no one to see what I did in the privacy of my own home?  Um hmm.

And I enjoyed it.  But I still felt like it was wrong.  By now, I completely understood that a guy wearing women's underwear wasn't really a man.  I didn't need my mother to beat me to make me understand.  Add in that my wife just left me for a man, and that I knew I'd never fucked a woman.  I was a quiet mess.  Quiet because I could never, ever, admit the truth.  But, things improve.  Next post.  Stay tuned.

Read more »

Off To College - Panty Raids!!!

Can anyone guess what happens to a sissy who goes off to college?  Up until this stage of my life, while living at home, between my mother and sister, I had a steady supply of easy access panties, etc.  I had plenty of opportunities to dress up, and even more as I got older and found that my parents trusted me to stay home alone.  But then, alas and alack, I graduated from high school and went off to a small college in North Carolina.  And when I went to college, the dorms weren't all suites where each student had their own private room, like many colleges today.  No, I shared a room with two other guys who I'd never met before.  And we had a common shower and bathroom down the hall, that we shared with everyone on our floor.  There was virtually no privacy.  And certainly there was no access to panties.  

So, there I was - cold turkey - cut off from my obsession with wearing women's underwear.  I never, ever could have gotten up the nerve to go to a store and buy my own.  And besides, where would I keep them?  Right.  No way I could do that in a dorm room.  I may have been reckless enough to get caught by my mother.  But I was no idiot.  If I ever was even suspected of such a thing at college - especially a small Christian based one such as the one I attended, I'd be ruined forever.  Heck!  I would have had to transfer to a different school.  And how would I explain that to my parents?  And thus began a long dry spell, broken only by visits home on holidays.  But even then, the nature of holidays meant relatives would be visiting and so I didn't have as many opportunities to sneak into my mom's hamper.  It was frustrating.

There was one aspect of college life, though, that I had not known about before matriculating.  Panty Raids!  That's right.  The one time that a guy like me could openly go after panties.  But even then, I felt extremely self-conscious about my zeal, lest anyone think I was too overly excited about the mission.  And then, when we got some, I couldn't really keep them.  Guys just naturally feel uncomfortable being open about obsessing over panties.  But you know what I think now?  I think most guys get excited about women's panties.  I really do.  That sissies like me have to be so sneaky, even as adults, is kind of dumb.  I am confident that most guys have probably snuck on a pair of panties at some point in their lives - and liked it!  That idea is at the root of most of the guys being tricked/forced/dared/lost a bet into panties stories that you read at sites like Fictionmania.  They're just too macho and all to admit it.  Due to the teasing they'd suffer.  And so, sissies like me continue on in private, wearing our girly clothes and putting on a male front to the world.

So, that was college.  And while we're on the subject of Panty Raids...

An Actual Panty Raid - Much Like The Ones I Went On At College

 

Visit Panty Raid, a really cool lingerie store in Los Angeles

Post Panty Raid Victory Party

Panty Raidpalooza!

Outed After Panty Raid

 

Read more »

Bikini Panties!!!

As I mentioned in an earlier post, at some point, after the disastrous day my mother and sister caught me dressed up all sissified in my mother's lingerie, I forgot how awful the beating was - no - that's not actually correct - I never forgot how awful that day was - I simply could not resist the pull.  I had to wear women's underwear.  I could not resist.  I've never been able to.  But, nonetheless, my mother's effort to "teach me not to be a sissy," didn't take.  Perhaps, if she'd caught me several more times, it may have taken.  But, thankfully, she didn't.  You know though, I often wonder if the beating she administered to me that day hurt her as much, if not more, than it hurt me.  My mother loved (loves) me.  I know it had to be an awful thing for her to find her only son dressed up in her lingerie.  I mean, picture the scene.  She walks in the house with my older sister in tow, and her nine year old son is flitting around wearing her DDD bra stuffed full, her dirty underwear, a girdle with stockings and heels for crying out loud!  How was she supposed to react?!  And I also wonder if, despite me thinking it was simply because I was always so much more careful to not get caught, the actual truth was that my mother decided to try not to catch me again.  Maybe she didn't want to have to beat me like that again?  Maybe she loved me so much that she decided that a little innocent, if perverted, exploration by her son wasn't the end of the world?  I don't know.  I'm just wondering.

But the point is, I eventually went back to my mother's dirty clothes hamper.  As a young boy, I would continue to dress up in as much of her clothing as I could find in her hamper, including slips and nylon nightgowns.  I feel so blessed that my mother grew up in the generation of women who bought in to the idea that nylon was the feminine lingerie fabric of choice, rather than cotton.  Cotton has its uses as a fabric to be sure, but for me, as a sexy material for lingerie - ugh!  

As I got older, so did my sister, who was five years older than me.  And as she got older, her girls lingerie transformed.  She and I shared a bathroom.  Thus, we shared a dirty clothes hamper.  Sooo, I was always checking it out as well.  One day I discovered something new and exciting - to me at least.  I discovered a pair of nylon, bikini styled panties, with a flowery design in the material.  Not all of the panties women wore were white?  Not all of the panties women wore were full-bottomed?  Oh my God!  I slipped them on.  The first thing I noticed about my sister's new panties was the way they pulled my little penis up tightly to my crotch.  Suddenly, I didn't need a girdle, or a feminine napkin holding my penis close to my crotch in order to create a feminine appearance in the front.  The snug fitting bikini style panties accomplished that goal!  And I loved the feeling of constriction!  

And so, a new chapter in my panty ways began.  Make no mistake, I didn't stop sneaking my mother's panties.  As I've mentioned, Vanity Fair Lace Nouveau will always be a staple in my panty collection.  (Speaking of panty collection, stand by for a posting in the near future when I share mine.)  But, I also enjoyed many years of wearing my sister's broad array of sexy panties that only a teenaged girl would have in her collection.  Or, so I thought at the time.  I mean, I know now that I was a sissy then.  But then, I didn't know what I know now.

And just so we are clear, the following are some illustrative examples of the variety of panties I was able to enjoy through my older sister.

These?

Or, how about these?

Maybe these?

No?  Okay, then these?

Or, perhaps these?

Or these?

These?

No?  Then, for a sissy, definitely - these!

 

Read more »