First Full Day in Mexico - Day Two

[NOTE - Anyone who is just beginning to read my blog might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart – Our Weekend Apart Aftermath – Cheerleader Has A Heart-To-Heart With Sissy - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl - Cheerleader Learns – Juggling Isn’t Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment – My Cheerleader and Her Quarterback -  Cheerleader and Sissy Reach Accord (And Satisfaction) - Sissy Catches Up, Cheerleader Goes Sailing - Discovered! - It Was Bound To Happen Sooner Or Later - Quarterback Discovers Leeanne - I Have Good News. And News - Quarterback Is Visiting For Labor Day - Cheerleader Speaks - My New Sissy Life - Kittens Love Cream - Sissy Belongs to Cheerleader - Santa Claus Is Coming To Town - Bath Time - Christmas Shopping Visit Summary - Cheerleader and Sissy's Christmas Surprise - We're Going To Mexico! - Mexico - Day One. These are the previous posts that tell the story about my sissy journey.]

Our first full day in Mexico was interesting  For the most part, we lounged around and tried to catch up from jet lag on our first day of travel.  I have already become quite comfortable with the attention of Mercedes.  And likewise, I think she has taken a special liking to me.  She is a sweet and very pretty Hispanic woman.  In addition, she seems well attuned to what is going on between me, my cheerleader and her quarterback.  At first I wasn’t certain that she knew our actual relationships, but in talking today I learned that she knew my cheerleader and I were married and that I’m her sissy cuckold to her and ex.  She told me as she helped me with makeup this morning that she thinks it is sweet that I love her so much that I permit her to be so free with a real man.

Quarterback and my cheerleader slept in on Sunday.  Mercedes helped me with makeup and then told me that I was to wear my babydoll that I’d slept in to breakfast.  Without panties.  Which meant my chastity-caged clitty was on display.  When my cheerleader and her quarterback came to breakfast, he was wearing gym shorts and a tank top, while she wore only a sheer red negligee robe that hung open and nothing else.  In fact, she wore that all day.  The week was off to an interesting start if Sunday was any indication.  Quarterback and cheerleader joined me at a table by the pool while Mercedes and Maria brought us coffee and breakfast.  My cheerleader was all over her quarterback, and he made himself comfortable fondling her wherever he wanted.  Within the first ten minutes of us sitting there he had her on her knees sucking his cock in front of me.  When he finally came in her mouth, she came over to me and kissed me, sharing her mouthful of his cum with me.  It was an embarrassing scene, and I understood that anything could happen the rest of the week.

After breakfast we went back to our rooms to dress for the day, although “dressing” was a relative term, as it turned out, for my cheerleader.  When I saw her after Mercedes helped me get dressed, she was wearing a tiny red thong bikini that barely covered her pussy and highlighted her smoothly shaved cameltoe, and a top that simply added colored highlights to her full breasts.  I, on the other hand, was another thing altogether.  I wore a pretty flowered full-bottomed bikini and matching full-cup top that held my large breast forms nicely.  I also wore a pair of pink six-inch open toe high heel sandals and my pink wig, and a pair of clip on hoop earrings.  I felt so feminine and sissy in my bathing suit and loved being able to openly dress that way in front of everyone.  Mercedes told me she thought I looked very pretty, for a boy.

For the rest of the day we laid around by the pool, and during the day my cheerleader was devoted to satisfying her quarterback’s every sexual desire, while I, more or less, observed.  My job was to clean them off whenever they fucked, which was frequently.  For most of the day my cheerleader was naked as her quarterback feasted on her.  She seemed different to me as I watched her submitting to him.  And as for me, I began to feel comfortable being an observer of their relationship with each other.  I wondered if this was what it was like for them when I was not around, like when she would visit our hometown without me and see him then.

As evening rolled around, we all retired to our rooms to shower and get ready for dinner on the veranda by the pool.  Mercedes helped me shave all over and then helped me dress in a pretty light blue sundress with matching heels.  I wore a pretty light blue matching French cut lace bikini panties and bra underneath.  She made up my face to look very soft and pretty, and I again wore my pink wig.  My cheerleader wore a very tight, and very short, black sheath dress, under which I could tell she wore no bra.  She looked radiant as she sat for dinner.  Quarterback also looked handsome wearing a pair of black Bermuda shorts and a tight black t-shirt that highlighted his excellent physical build.  My cheerleader and he made quite the lovely couple.

During dinner quarterback asked how I was doing so far.  He wanted to know if I liked Mercedes.  I assured him that I was doing fine, and that Mercedes was treating me well.  He seemed happy to hear that and then told me he had plans for us to go out the next night together, the three of us, and asked if I was okay with doing that.  By him asking, I suspected he meant that I would be dressed in a feminine manner.  But to be clear, I asked what I would wear.  He smiled and said, “I don’t know for sure, but it will be a dress, if that is what you are asking.  So?”  I looked at my cheerleader and she nodded to me.  Then I said, “Okay.  I think I can do that.”  He smiled and said, “Good girl.”

We passed a quiet evening enjoying the view of the ocean and relaxing until quarterback and cheerleader excused themselves to their bedroom.  I stayed up for a while, but then turned in alone.

Mexico - Day One

[NOTE - Anyone who is just beginning to read my blog might want to read the following early entries in my blog about my sissy journey before reading this latest entry: A Little More Background - Am I Sure I Should Do This? - I'm Afraid - These - Where It All Started - Then, These - Miss Flo - Caught For The First Time - About My Last Post - Bikini Panties!!! - A Virgin Bride (And Groom) - Exhausted Sissy Needs Stress Relief! - Sissy Marries Cheerleader - Sissy Makes Life With Cheerleader - Cheerleader Discovers Sissy - Cheerleader Accepts Sissy - Cheerleader And Sissy Grow - Cheerleader Asserts Control - Cheerleader Teases Sissy - Cheerleader And Sissy Settle In To New Home - Cheerleader Cucks Sissy - Cheerleader and Sissy Are Mentored - Sissy Offers Context For Cheerleader - Sissy Sees Her Future - Sissy Adapts To Chastity - Sissy And Cheerleader Spend A Weekend Apart – Our Weekend Apart Aftermath – Cheerleader Has A Heart-To-Heart With Sissy - Sissy And Cheerleader's Last Weekend With Andrea - Part One - Sissy And Cheerleader's Last Weekend With Andrea - Part Two - Cheerleader Thanks Sissy - Cheerleader Does A Sleepover - How My Cheerleader Vets Men - Cheerleader Flirts - With Purpose - Cheerleader Is A Happy Girl - Cheerleader Learns – Juggling Isn’t Easy - Cheerleader Gets An Itch - My Cheerleader's Summer of Contentment – My Cheerleader and Her Quarterback -  Cheerleader and Sissy Reach Accord (And Satisfaction) - Sissy Catches Up, Cheerleader Goes Sailing - Discovered! - It Was Bound To Happen Sooner Or Later - Quarterback Discovers Leeanne - I Have Good News. And News - Quarterback Is Visiting For Labor Day - Cheerleader Speaks - My New Sissy Life - Kittens Love Cream - Sissy Belongs to Cheerleader - Santa Claus Is Coming To Town - Bath Time - Christmas Shopping Visit Summary - Cheerleader and Sissy's Christmas Surprise - We're Going To Mexico!.  These are the previous posts that tell the story about my sissy journey.]

My cheerleader and I woke up early Saturday morning to get ready for our flight to Mexico.  The day before, as I drove home from work, I received a text message from quarterback.  He wrote, “I have given your wife a task to perform when you get home.  Now I’m giving you one.  Cooperate with her.  What she is going to do is only temporary for our trip.”  When I got inside, she called out for me to come upstairs.  When I got up to our room my cheerleader was in our bathroom.  She had laid a piece of plastic on our floor and told me to get undressed and come in there.  When I joined her in the bathroom, I could see have an electric razer.  Uh huh.  She was going to shave me completely.  Underarms, chest, legs, and yes, all of the hair around my clitty.  I was completely shaved and smooth, and realized I would be the entire trip to Mexico.

We wore jeans and t-shirts that had been selected for us by quarterback's assistant for the trip to Mexico.  Mine were tighter than my usual male jeans and that was because they were jeans cut for a woman, resulting in a very tight fit.  His assistant had calculated that and, to help me tuck and contain my sissy bulge, she also sent me a pair of tight girdle panties complete with butt padding to make sure the jeans "fit right."  I wore cowboy boots as a substitute for high heels, also ensuring that my enhanced butt was emphasized.  I may not have been wearing a bra or makeup to make me appear feminine, but I definitely felt feminine.  

When we met up at the airport, quarterback set the tone for the trip.  He pulled my cheerleader close and kissed her hard as I stood by and watched.  Upon boarding the plane, I realized that my cheerleader’s seat was next to her quarterback, while I was across the aisle.  During the trip, I was more or less alone while my cheerleader snuggled up with quarterback.  When we finally landed in Mexico, I was tired from the flight.  We were met at the airport by a driver named Pedro, who loaded our luggage into a Landcruiser, and drove us to our private villa in Mazatlan, Sinoloa.  Once there we were greeted by two pretty Mexican women, Mercedes and Maria.  Pedro carried our luggage inside, placing my luggage in one room, and my cheerleader and quarterback’s in the one next door to me.  The villa was wide open and had an amazing view of the Pacific Ocean. 

Mercedes came to my room and told me in somewhat broken English that she was there to attend to any of my needs, and to help me dress as needed for the week.  I know I gave her a look of confusion, but she quickly explained.  She knew I was a sissy and that my cheerleader was my wife.  She assured me that she was not there to judge me - only  and to help me present myself in as pretty a manner as possible for the week.  Finally, she whispered in a conspiratorial tone, "Your secret is safe with me sissy."  And she wasted no time as she helped my unpack my luggage and put it away in my closet and drawers.  She immediately began to run a hot shower for me to refresh and to shave completely.  I was not to have any stubble for the entire week, which would mean daily full body shaving to maintain what my cheerleader had done on Friday evening.  Then she sat me down and applied glue on fingernails and painted them a deep red, as well as my toenails.  When she finished, she began applying makeup to my face, darkening my eyes and painting my lips a deep wet red.  She then had me put on a pink flowered swimsuit and told me to fill them with my large breast forms.  She helped me slip into a pair of pink high heels to wear with my swimsuit, and finally fitted my pink wig onto my head. When she was done with me I looked completely sissified.  She told me I was to go out by the pool to relax while she and Maria served drinks.

As I walked out by the pool, I saw my cheerleader and her quarterback were already there.  Quarterback was sitting on the edge of the pool and my cheerleader was in the water between his legs as they dangled in the water.  As I got closer I could see she was topless and had his cock in her mouth.  Already.  Quarterback was leaning back while she slowly and lovingly sucked him as I stood by them and watched.  She sucked him until he came in her mouth and she took all of him.  I don’t know how to describe how I felt standing there in my swimsuit looking so sissy while my wife sucked him off, but it definitely set the tone for what I might expect for the trip.  When she finished, she crawled out of the pool wearing only her white lace bikini bottoms, dried off and sat down on a chaise lunge chair, joined by her quarterback and me.  Mercedes and Maria brought us drinks and some fresh fruit and the three of us relaxed together by the pool.  After about a half and hour, quarterback said, “Come here sissy.  I need you to get my cock ready for your wife.”  I stood up and went to his chair and then kneeled down beside him and slowly began to lick and suck him until he became hard again.  When he was good and hard he told my cheerleader to come to him.  She straddled him on his chair and slowly sank onto his hard cock.  Then, as I kneeled by his chair, she slowly and deliberately rode her quarterback’s cock until he made her cum a few times.  When he finally came inside of her, she moaned so loudly and cried out, “I love your cock Tom!  So much!”  He laughed and said, “Good.  Because I plan to fuck you whenever I want to this week.”  Then, to me, he said, “Okay sissy.  Clean us up now.”  My cheerleader slid off of her quarterback and snuggled beside him.  I took his cum covered cock into my mouth and sucked him clean, and then leaned in and began sucking his cum out of my cheerleader’s swollen pussy.  The tone was set and I knew my role for the trip.

Now, as I write this quick update to day one, my cheerleader and her quarterback have gone to bed, and so have I.  I’m exhausted from the trip and look forward to sleeping in tomorrow. 

 I admit I'm anxious about what the rest of the week will bring, and I had trouble sleeping last night.  It's early Sunday morning and I'm sitting up in bed finishing this post about Day One.  I know my cheerleader and her quarterback were up for a while last night as the villa is very open and I could hear them together in their bedroom right next to mine.

Sissy Getting Out of Another Ticket

Sissycumtini

Nurtured and Loved

This photo says it for me, as a sissy.  My male sexuality harnessed and controlled for the benefit of my wife, and me, in the warm and loving hands of the woman who has permitted me to grow as the feminine being that has been trapped inside of my male persona for most of my life.  I love her dearly in so many ways, not least of which is how she has nurtured my true nature.