Sissy Cuckold Frustration

i hate thongs.  Yes, they look very sexy on many girls but on a sissy (even ones with the tiniest of clitties) i just don't think they look nice.  And since i don't think they look nice, i don't like wearing them.  And since i don't like wearing them....well, so on and so on.

Diane knows all this and after what happened yesterday, it's safe to assume She shared this information with Her lover Paul.  The information along with some plotting on their part made for a very frustrating and humiliating afternoon for me.

It all began when i received a response from Paul to my daily Chastity Report email.  Here it is verbatim:

Sissy,

You'll be happy to hear I'll be over this afternoon at 2 PM sharp.  And you're probably even more excited to know I have another errand for you to run where you will get to spend a little more of your Victoria's Secret gift card.  Like that?  

Today's shopping list is small, just like the things you're going to buy.  You're to buy two lacy thongs.  One for Diane and one for you.  Her thong in black and yours in pink.  Make sure you buy the right sizes, we don't want those pretty things to go to waste right?

I expect you back with the thongs before I get there.

Sir

The email came in shortly after 10:00 AM yesterday not long after I had finished yesterday's blog post.  Paul's noting to buy the right size was an obvious reference to that post.  And the requirement to buy each of us a thong?  Certainly Diane must have let him in on my distaste for them. 

I had a couple of other things to do and when I looked at the time, realized that I would have to get going soon if I wanted to be back in time.  I mentioned the email to Diane and She suggested that "you get your pretty little ass in gear and go shopping."  i was gone in about 10 minutes.

i did my other errands first before i went to Victoria's Secret.  i was my regular nervous self but found what i was supposed to buy and got the usual courteous service from the sales personnel at the store.  It was before noon and the store wasn't that crowded.  i'd be home before one in plenty of time before Paul's scheduled arrival.  i even stopped at a Starbuck's drive thru for a coffee.

Wasn't i surprised when i pulled up the driveway around 1 PM to see Paul's car parked in front of Diane's garage door.  My sissy cuckold mind imagined Paul himself pulled up right behind Diane in our bedroom, just like the front of his car had pulled up next to Her's by the garage.  My imagination wasn't that far off.

Paul and Diane were already in bed together.  It was 1:05 PM.  The bedroom door was closed with a note taped to it that read "Do Not Disturb!  We'll call for you P."  i could hear some soft moans and giggling behind the door.  They knew i was there, our security system has small chimes that go off (one of them is in the master bedroom) when certain doors to the outside are opened.  i had entered the house through one of those doors. 

i waited until 1:43 PM before i was called.  Diane opened the door and called down to me to come up and bring the thongs.  When i entered the bedroom both Paul and Diane were nude, She standing near the bed and Paul laying on it relaxing.  "Strip down and join us for a little while" Diane said then gave me a kiss. 

Stripping down to nothing but my CB-3000, even though Paul's seen it before, was more humiliating than ever.  Probably the circumstances of the whole scene made me feel this way.  While i stripped Diane had gone into the bathroom to retrieve some small scissors to cut the tags off the thongs.  She held them each out and inspected them, taking Hers and holding it in front of Herself while doing a little sexy dance while facing Paul.  He liked what he saw and chuckled. 

"Why don't you slip Diane's on for Her?" he suggested.  It was more than a suggestion and i did it.  Diane handed me the thong, i knelt in front of Her and guided the garment up Her lovely thighs so that it fit nice and snug.  She grabbed my head and pressed it against Her crotch.  i kissed it.  She held me there long enough for me to get an appreciation for Her wetness, probably the result of some heavy foreplay but i didn't think Paul had made "full love" to Her yet.

"Sexy! A perfect fit too." Paul said.  "You're turn, put the pink one's on."

i put the pink one's on quickly and felt silly.  The front of the thong didn't cover the CB-3000 real well.  my stiffled erection was a non issue since it was confined in the plastic dungeon and the back of the thong felt uncomfortable as it nestled between my ass cheeks. 

"Cute!" Diane teased.  "Turn around and show us your pretty little butt."

i did and Diane quickly gave me a swat on the ass. 

"Thank you" She said.  "You can go now.  Go check the laundry room.  There's some ironing to do."

That was it.  i was shocked, embarrassed, humiliated and then some.  i went to pick up my clothes and Diane stopped me.

"No no.  Just like you are now.  Scoot."  There was another slap on the ass.

i left the clothes there and hurried out of the room.  i was alone with my thoughts doing some ironing for some 45 minutes.  There was a pile of clothes in a basket that Diane had taken out of Her closet to be ironed.  Tucked in the middle of the pile were a pair of Paul's slacks that I hadn't seen at first.  Ironing his slacks became the most humiliating cuckold task i've done to date.

my ironing was interrupted when i heard Diane call out.  "Did you get to Paul's pants yet?  He has to leave soon."  i replied that i had and Diane told me to bring them up to the bedroom.  i did and when i got up to the bedroom She was at the door  waiting.  She kissed me, took the pants and closed the door.

i was in the laundry room when Paul left.  He didn't say good bye or anything.  Soon after he walked out the door Diane told me to meet Her upstairs.

i was finally physically involved.  Paul was gone, but had left me a reminder of his presence there that afternoon.

love,

sissy terri

read more

Another Cuckold Errand

Yesterday's errands led to a rather interesting discussion with Diane last night.  She didn't call me back until she was in her car and on her way home from the office, even though I had left her a message to call me earlier in the morning.  Her delay just seemed to be another way to tease me.  Of course lately, I'm viewing just about everything she does in that way.

"I didn't get a chance to call earlier, it's been a hell of a day.  What's up?" she asked.

What's up????  It wasn't that I expected a flowery greeting or anything, but I would have thought that she had a general idea about why I was calling.  It was as if her shopping list that included condoms for her to use with Brian was no big deal.  Again, her brief greeting seemed like it was intended to make me broach the subject first.  It worked.

"Not much, I did get a lot done today" I told her.  "I called earlier to ask you about the list of things you left me.  I was just a little surprised."

She laughed a little and said "Oh that,  I hope you didn't expect me to have unprotected sex did  you?"

"Of course not" I answered, and before I could continue, she told me she had another call coming in and would either call me back or see me when she got home.  She didn't call back and was still on her phone when she walked into the house from the garage but quickly said good bye to whoever she was talking to. 

"So, let's talk about your little shopping trip today" she said as she made her way to kiss me.  She told me to pour each of us a glass of wine and and we sat down in the living room to talk.   "I want to see the condoms you bought" she said, so I went to our room to get the package I had bought earlier.   The ones I bought were Trojans and were called "Her Pleasure Ecstasy."  She looked the package over, put them down, smiled and gave me a big hug.

"You're always so thoughtful and willing to please me.  Even in the brand you selected!" she said, "Just like a wife who wants to please her man, getting him something she thinks he'll like.  Putting him first.  You always put my pleasure first, and I love that."  She was right, and I love doing things for her.  She does know how to make me feel appreciated.  But the discussion took an interesting turn from there.

"I'm not sure these condoms are exactly what I want though.  Brian might appreciate something more manly.  Just like you want to please me, I want to do little things that will please him.  In other words, put yourself in my place.  You'd probably choose another style wouldn't you?" she asked me.  I wasn't totally convinced, but agreed just the same.

Obviously, I've paraphrased our discussion and quoted it as best as I could remember.  The gist of the conversation, which essentially began with the condoms I had purchased, was about me changing my frame of mind when thinking about her and Brian.  In essence, when doing things to please her, I should be focused on how Brian wants to be pleased. 

When Diane and Brian finally hook up, and all indications are that it is going to be very soon, he'll be doing it under the assumption that I don't know anything about it.  Little will he know that because of Diane's cleverness, I'm going to be totally cuckolded and trying to please him through her. 

After dinner, Diane spent some time on her laptop while I cleaned up.  She was on the computer for awhile, checking her facebook, personal emails and a few other things.   No doubt she did some research on Trojan condoms.  I'm on my way to the pharmacy this afternoon to buy some Trojan Magnums. 

read more

A Cuckold Errand

I usually do some errands on Thursdays or Fridays in preparation for the weekend.  Diane wants to enjoy her weekends as much as possible and it also feels pretty nice that she also wants to spend them with me.  Rather than run around doing errands on the weekends, she wants me to take care of those things on either Thursdays or Friday.

Last night after dinner I was cleaning up and doing some dishes in my apron while she was on the phone with her friend Linda discussing some work-related issue.  Linda must have had to take another call and while Diane was waiting she asked me when I was planning to do my errands this week.  I told her I would probably go this afternoon since I was going to the gym in the morning.  "That's fine.  I'll leave you a list of some things I need" she said.  That wasn't unusual since she always leaves me a short list of things she might need or want.  These can range from a grocery item to more womanly things like a high end cosmetic item.  I've gotten very accustomed to buying these things for her at the Macy's cosmetic counters!

Just as I got ready to leave for the gym this morning I happened to glance at the list of about eight things Diane had jotted down.  One word jumped right out at me and stopped me dead in my tracks:  "CONDOMS :)"  I don't know how I had missed it before.  I had walked by the not which was sitting on the counter near the kitchen wall phone where we always keep such things.  In addition, it was the only item in all CAPS, and with that little smile after it.

Talk about a strange feeling.  The realization that my cuckolding might be just around the corner.  Nothing of the sort had been discussed for a couple of days.  Instead, one word amidst a list of items for me to pick up on my weekly errand run.

I tried calling Diane at her office and her private line bounced over to her administrative assistant.  She was in an all day meeting.  I asked to be put through to her voice mail and left her a message to call me when she has a chance.  I'm not sure what I'll say to her.  I'm not angry or anything, but curious as to why we didn't talk about it.  In some ways, I'm not surprised.  What she did teases me in an indirect yet very effective way. 

Anyway, I'm going to do what I'm told.  By the time she calls back, I'll probably already have purchased the condoms.

read more