DISCLAIMER: This story is about Femdom, Cross Dressing and Cuckoldry. If these topics offend you please don’t read it… Just move on. No need to vote or comment if this isn’t your “thing”. If these appeal to you, please enjoy.
-IT’S NOT ALL ABOUT HER-
I absolutely hate trying to get anything off of my husband’s computer, but here I was trying and failing yet again to get something done for him that he should have done himself. I always get lost when using his computer because he sets things into multiple files and they look nothing like the files on my computer.
After an hour of searching, I finally find the file he asked for and email it to his work, …’There. Done with that annoying task… ‘
But just as I’m about to slam the lid closed I notice a file that’s labeled… “AO”
Hold on a second, I recognize that… It’s is a code!
A long time ago when we would send any ‘inappropriate’ emails or pictures we would include the code “AO” in the title that way we wouldn’t open them at work, in front of kids, friends or at an embarrassing moment. What was a file named AO doing in his business files i thought? So I moved the cursor to the file named AO and clicked. There were two sub-files…
I clicked on the personal file, it was filled with all the naughty pictures and video that we had shot throughout the years. He loved his little trophies, I thought most of them were unflattering angles and shots of me, but he really enjoyed them, so I didn’t mind.
When I clicked on the public file it too was filled with more folders, all neatly labeled and sorted.
I opened each one and found an assortment of videos and still pictures of the various categories, most of which I had seen before (he never hid any of this from me and we were always open about watching porn).
Then I got to the last one… ‘Pegging’
That was a term I had not heard before, and was interested to see what it was. When I clicked on the first video there was a woman standing there with an apparatus attached to her like a leather girdle. What the hell does she have on I thought … Then it hit me, it’s a strap on dildo. I had seen them in the store and in pictures but never in action.
As the action continues it becomes increasingly apparent that this huge plastic dong isn’t meant for a girl… Because there is a willing hairy man butt lubed up and ready to take what she’d be dishing out.
I was a little taken aback, he has a whole file dedicated to this activity?! As I move the cursor to back out to the pegging file I see that he has over a hundred of these videos! I scroll down a choose another video at random. Similar activities except this time the guy in the action is dressed in stockings and panties.
A quick look at some of the other titles it becomes obvious that these are almost all cross-dressing ‘sissy’ videos. I watch a couple more and realize that these videos are making me wet… The thought occurs to me… Would I like to see my hubby in panties sucking and getting fucked by a dildo? I think the increasing dew between my legs gave me the answer I needed.
A couple nights later when we were settling into bed I asked him if he wanted to watch something ‘educational’ (Our inside term for watching porno prior to our lovemaking session.) I moved his laptop into position so we could both see it… I scrolled to the “AO” file and found the pegging section. I selected a long one with a good title…”Sissy Training”.
When the video began he was still propping up his pillows and wasn’t paying close attention to the movie I has selected. When he finally got settled in, he saw what the video was, “Where did you get this?” He Said.
“Oh I found a whole bunch like this.. In your pegging file, and I thought tonight you might like to watch some of these with me”! He looked a little embarrassed, but soon enough the movie drew all of his attention.
As we lay there caressing each other watching the movie, I noticed that his cock was stiffening without even having to be touched… He obviously was enjoying the video, and while he was engrossed in the movie I excused myself to go use the potty. When I reentered the room he was transfixed to the computer screen and was oblivious to me…I made my way over to the dresser and pulled out a bag that I had previously stowed there earlier in the day.
As I slipped back to the bed he barely noticed, completely engrossed in the video. “Mike”, I said, “I went shopping today and got some new panties and a new sex toy, want to see them?” His gaze never left the screen.
“Sure hun, put ’em on.”
I stood up and walked to his side of the bed and began to slip the panties over his legs, that got his attention. He suddenly was paying attention. “what are you doing?” He chirped.
“Well” I said. If you’re going to be a proper sissy you need to have your own panties don’t you?” I purred. “You certainly can’t fit into mine.” He was speechless.
Then I showed him the strap-on I purchased. konya escort It was one of those cheap unrealistic plastic monstrosities, but it was on sale… I didn’t want to lay down the $150.00 for the good ones if he totally freaked. I figured I’d make a small investment at first to test the waters.
I told him to stand up and pull up his panties and check himself in the mirror, this he did with more than a little reluctance.
“This is OK with you?” He asked…
“Actually, it’s kind of a turn on for me too”, I said. I watched as he ran his hands over the silky softness of his new panties and looked in the mirror to see what he looked like.
“Feel good to you?” I asked. He didn’t say a word just leaned over and gave me a big kiss, I’m pretty sure that meant thank you. As time passed he got more outfits and I actually made him wear nothing but women’s clothing a whole weekend and he was in heaven. Several times I even made him wear panties to work.
Our strap-on’s improved over time too. I found that most of the cheap ones were uncomfortable and lacked any real sexual stimulation for me. Then we found a brand of ‘strapless’ strap on’s and the world changed.
These were more lifelike didoes that fit inside me and made it so I could cum just having him stroke it like he stoked his own cock. More and more, it became a regular part of our lovemaking, he like sucking my cock and he loved being ‘pegged’. He was becoming just like the sissies in his favorite videos.
I wanted to take it further, and I sensed he did too, so one night while he was sucking my strap-on and moving me deliciously close to my third orgasm of the night. I jokingly asked him if he’d give me a BJ in public. (He loved when I’d suck his cock in a park or other outdoor venue so I figured turnabout is fair play).
He looked up without hesitation with saliva from his now expert blow job running down his chin, and said an eager,
“Yeah, I’d blow you in a park”. That set my nasty plans in motion.
It had taken me more than a month of planning to set this night up, but if it worked out like i’d hoped, this would be a night to remember. For at least a week leading up to the ‘night to remember’ I had found one reason or another to put off any sexual activity between us, so I knew he’d be hornier than usual. I texted him at work to see if he could get home a little early so we could get a jump on our date night.
MIKE: No prob
ME: Hey, why don’t you meet me at the Hyatt Hotel Bar at 4:00
MIKE: Not home?
ME: No Hotel bar 4
HIM: Sounds good
HIM: Do I need to stop for anything?
ME: Nope I got it ALL.
When he arrived at the bar I was already two Mojito’s in and feeling fine. He walked up, kissed me on the cheek and sat down.
“You look beautiful” he said motioning to the waitress to come to our table so that he could order.
“Oh I already placed an order for you, and Sharon will be here shortly with it”…
“Oh, Sharon is it… Been here long”? He quipped. “Long enough to have two of these, order a drink for you and know her name is Sharon!” I snapped back with a wry smile.
When Sharon brought his drink it wasn’t his usual, heavy on the alcohol and light on the mix drink he usually has. But a fruity condition that this bartender is known for.
You’re going to have a more appropriate drink tonight I said.
“Appropriate?” He asked. “Appropriate for what”?
“Well, if you’re going to be dressed like a lady, you should drink like one, and not smell like a distillery”. I said.
In a very sarcastic tone and looking at his work attire… “Well I’m not dressed like a lady, now am I”. He noted.
“We will fix that soon enough”, I said. “Now finish your drink without another word, or we’ll call this whole evening off. I’ve planned a beautiful evening and if you’re not going to play along, we can just go home now.”
There was enough firmness in my voice to let him know that I wasn’t joking, and enough playfulness to make him realize he really wanted to play along.
“Sorry dear, I was just noting that I’m not wearing women’s clothes and you’re not carrying a bag… Soooooo” his voice tapered off as Sharon approached asking if we’d like another drink.
“Not right now Sharon, we have to go freshen up. I said, Can we take our drinks up to our room?”
“Of course you can, would you like to leave your tab open?” Sharon asked.
“Yes, that would be wonderful, we’ll be back in less 10 minutes.”
Mike sat upright in his chair. “Room… We have a room? Here? This place is like $300 a night!”
“Hush, it’s more like $200, and I’ve pulled a few strings so it might even be free. Now the longer you sit here quibbling the less time we have for fun!” I said in my best kids TV show voice. “And besides I’ve been saving for this for months… SO SHUT IT MISSY!” My tone was more stage mom and less Mr. Rogers, by now.
“OK OK OK” he groveled. “Lead the way.”
I gestured to our left where the elevator’s were located.
When we got to our room he was quite konyaaltı escort surprised to find our toy bag, the video bag, an assortment of liquors and mixes, and on the bed a whole new outfit for him to wear. There were pumps, stockings, panties, bra, shape wear, wig, skirt, blouse, fake nails, make-up, brushes … Everything was new except the wig and pumps, those we had acquired over the ensuing months.
As his eyes moved over the room all he managed to mutter was …
“How long have you been here?” he asked.
“Almost all day,” I said proudly.
“Wow… Just wow.” He repeated.
Then it started to dawn on him…
“Wait I’m not going back down to the bar dressed in all that. There’s no way I would pass for a woman! No matter how much you doll me up.”
“Well”… I said, “you are right, you are not going dressed in ALL that, but you will be wearing most of it. First I want you to strip out if those boy clothes, go get in the shower and wash your body.”
He quickly stripped, and almost like a man possessed, was naked in front of me.
“Now, go take a shower and wash that man smell off if you.” I ordered. As he stepped into the shower I yelled above the din if the shower…
… “I’ve provided you with some body wash and scented shampoo… Use them both. You’ll also notice a nice new razor, make sure you shave your face extra smooth, no girlfriend of mine has a 5:00 shadow.”
The rest of him was pretty hairless, he’d been doing a good job if that. As he was wrapping up I told him to hand me the razor, so I could make sure the naughty bits were as clean as a babies butt. “I want this hole nice and pretty for the night activities.” I said, “can’t be a slut with a hairy butt!”
After he was powdered and scented. We moved back to the bed with all the clothes.
“Now, put your panties and bra on… This ain’t your first rodeo” I said as he quickly got dressed, as he was teaching for the skirt I stopped him.
“Hold on there. Let’s save those for later. You are right, we don’t want people to stare. I have some black slacks to go with that white blouse.The bar is pretty dimly lit, but anyone who looks closely will see your wearing women’s slacks, blouse, and a bra… But they’ll have to be close. And you can wear your man shoes over your stockings. And we will be giving you a bit of foundation, eyeliner and lashes. that bar is very dark so you should be fine.”
After dressing my girlfriend for the evening, we headed back downstairs to the bar.
I apologize to Sharon for being gone too long, “Sorry that took longer than expected, he just isn’t very good with putting on a bras yet”
She looked at me, then looked at him and them bluntly stated…
“Is he wearing your bra?”
“No, it’s his bra” I stated categorically.
She giggled, “Oh, can I get you two new drinks?” As if asking a mundane question would make the awkwardness go away.
“Yes we would.” I replied.
After about an hour of sipping our drinks and chatting, an attractive couple walked into the bar and sat at a table a few feet from us. After they ordered their drinks I asked my hubby/girlfriend, “What do you think of them? You’re always remarking how you can strike up a conversation with anyone do you think they are players?”
“I have no idea.” he stammered, “I have no way of knowing.”
“Well invite them over for a drink, let’s see where this leads.” I said emphatically. Mike got up and walks over to the couple and they exchange pleasantries and as he motions over to our table they seem to willingly accept his offer.
“Bonnie, this is Steve and Bonnie” Mike says in his best, host of the party voice.
There were handshakes all around as they settled in at our table.
We found out that they were from Santa Monica and they too were on a date night.
Drinks flowed and jokes were told and we all seemed to get along very well. Although both of them seemed to notice Mikes feminine attire and make up, neither commented on it. The conversation ranged from work to kids to hobbies. As the drinks flowed and the inhibitions lowered the conversation termed to sex. Steve joked that Bonnie should win an award for giving blow jobs. This seemed like the perfect time to step it up a notch.
“Steve” I asked, “have you ever had a man give you a blow job?”
That stopped the conversation in its tracks!
Mike just about spit his drink across the room.
Bonnie just stared at me.
“Uh… No” Steve said haltingly.
“I’ve heard that because men have a penis and know what feels good, they make the best cock suckers. Just like women are usually better than men at licking pussy.”
With that the table erupted in laughter. Bonnie chimed in, “I think that’s true, the best pussy licking I ever got was from a girl in collage!” Steve looked at her as if to say WTF? When she realized she may be hurting Steve’s feelings, she caught herself and patted his hand, “you’re great at it babe, but a girl is just, well, different.”
After konyaaltı eve gelen escort the talk had turned to sex, things progressed rather quickly.
Steve had been bragging earlier that he gives great massages, I thought this would be a perfect opportunity to take the next step.
“Steve, Mike has been complaining about a sore shoulder will you rub Mike’s shoulders?” I asked what seemed like a simple task, but Mike knew that by doing that, Steve would discover my girlfriends secret.
“Sure!” Steve boasted, “I give the best back rubs around, just ask Bonnie,” Mike squirmed in his chair as Steve positioned himself behind him.
As Steve started to rub Mike’s shoulders and back he said. “Oh, I can feel that you’re wearing a brace… Does it hurt that bad?”
“Go ahead and tell him Mike, he needs to know” I whispered in Mike’s ear.
“It’s not a brace… It’s a bra,” Mike sheepishly answered.
“A bra?! Steve asked. Why are you wearing a bra?”
Mike sat there… Speechless.
Bonnie spoke up. “What else are you wearing?” She purred.
As Mike sat there stunned… I leaned in and whispered.
“Tell them dear, tell them what you are.”
With a little hesitation, and slightly hanging his head Mike sheepishly answered.
“I’m a sissy slut and I’m wearing stockings garter, panties and a bra.”
Steve, while still rubbing Mike holders, whispers in Mike’s ear.
“Yeah, we know. That’s why we’re here.”
Steve’s revelation that this was a setup never occurred to him…
“Ah ha! I got you” I exclaimed “Bonnie and I met in an online chat group and have been planning this for over a month. Bonnie had caught Steve almost the same way I caught you and we wanted to explore the possibilities. We wanted to get together and teach you the ‘ropes’ as it were. In fact Steve should be wearing panties right now… Is that right Steve?” I asked.
“Yes ma’am,” was his subdued reply. “Good, then let’s close out our tab and move this party upstairs.”
As we walked to the elevator’s, I asked Bonnie if she brought her bag with her.
I had it sent up to your room just like you suggested and the Bell hop was more than happy to oblige.
I knew Mike would want to have a video ‘Trophy’ of the evening so when we entered the room, I had Mike set up the camera equipment so we could get that outta the way. I was so glad Bonnie and I had had some long chats via Skype, so that they were totally OK with recording this and that all the little details had been worked out.
“Bonnie,” I asked, “do you have your sissy under control?”
Bonnie turned to Steve, “Steve we need to see you in your panties.”
With little hesitation, Steve stripped down to some very pretty pink panties, there was only one problem. His rather large clit was jutting out in a ridiculous manner.
“Steve” I asked, “do you remember the question I asked you in the bar?”
What question was that Ma’am?” he quietly answered.
“I asked you if you’ve ever had your dick sucked by a man. Did you ever answer me?”
“No Ma’am.” Steve’s answer was quieter still
“No you didn’t answered me, or no you’ve never had your dick sucked by a man.” I queried.
Well, tonight you’re going to find out.
As I looked over at Mike I could see a look of trepidation in his eyes. “Mike, you have learned to be a good cock sucker on my fake cock, but now it’s time for the real thing.”
As Bonnie sank into the chair in the corner, I motioned for Steve to move to the foot of the bed and sit down. I told Mike he needed to lose the last vestiges of his man clothing, cause for the rest of the night he would be a cock sucking sissy slut.
“Mike, I want you to kneel down in front of Steve.”
There they were a sucker and a suckee, neither having done what they were about to do.
“Wait, wait wait!” I stammered “not just yet. Mike get into the bathroom and put on some lipstick, your wig, skirt and shoes, you need to look like the cock sucking slut you’re going to be.”
I turned to Bonnie, “if you’re going to be a slut, you should look like one.” We both giggled.
When Mike appeared from the bathroom he didn’t look like a hooker… But he looked like a man ready to play a roll.
“Ready for your first real cock?” I asked.
His response was in an affected female voice. “I think so.” was his hushed reply. Oh, he was ready.
Then get over here and pleasure your man. Mike gingerly walked across the room (he has not perfected walking in heels yet). He carefully maneuvered between Steve’s legs, where Bonnie had placed a pillow on the floor. He placed a hand on either of Steve’s knees and eased himself slowly down till he was kneeling on the pillow, looking like a princess waiting to please her King.
Mike started to use his blood red fake nails to run up and down the inside of Steve’s thighs and then to trace the outline of Steve’s ever hardening cock that was begging to be freed from its nylon constraints. When Mike’s hand made it to the waistband of Steve’s panties, he raised his hips so that Mike could pull them off. As Steve’s cock sprung free it was everything Bonnie had promised. It was about an inch longer than Mike’s and much bigger around. I knew that it would please Mike, because it was almost the same size as the strap-on we use.