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Sissy Panties

Sissy Panties

by Jimothy123
9 min read
4.57 (26100 views)
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It began innocently enough. Dave was browsing an online store killing time. He wasn't planning on buying sissy panties. He was thinking about his early marriage and how great the sex was and one thing led to another. His wife used to always wear lingerie or sexy panties whenever they made love. 20 years and two kids later, now she bought boring cotton panties and just wanted to do it missionary style. He started looking at panties to buy for her and started daydreaming about one time when they both put on pantyhose and had some wild sex. The feel of those hose was erotic and his dick started to harden at the thought. He started typing in pantyhose in the search bar and mens pantyhose was an option. Figuring he'd take a look just for kicks he clicked search. Different brands of pantyhose with a sheath filled the screen and also an icon for boy short panties with a penis sheath. His dick hardened more. Before he knew it he'd bought a 2 pack of sissy panties, one pair purple and one pair white. They were silk with a closed nylon sheath and were being delivered on Wednesday. He couldn't wait.

Wednesday morning while at work Dave got an email alert that the panties had been delivered. Luckily his wife worked late on Wednesdays, but he decided to take a half day to have more time to enjoy them. He left the office at noon and pulled in to the house shortly thereafter. He grabbed the package out of the mailbox and opened the front door. The dog ran outside as he walked in and Dave swung the door shut. Unfortunately for him it didn't shut all the way.

Next door Mike was trying to start his lawnmower, but it wouldn't. He saw Dave pull up and hurry into his house. He hated to bother Dave, but he just was inept at anything except IT work. Mike's wife and Dave's wife were best of friends. So naturally the two couples spent a lot of time together. But, Mike knew Dave wasn't thrilled at hanging out with him. Where Dave was tall and in great shape, Mike was short and thin. Dave was a man's man, Mike a little nerdy. Dave was a jack of all trades, Mike could barely hang a picture. That said, Dave was always nice to him and helped him with any handy work around the house, which meant Dave did all the work and Mike watched. It was embarrassing and he felt Dave did all that to belittle him in front of his wife. Mike thought for awhile before swallowing his pride and began walking over to see if Dave had time to look at his mower.

Dave was in his bedroom naked deciding which pair of panties on his bed to try out first. Purple. He pulled on the silk panties and slid his 7 inch cock into the nylon sheath. He instantly was rock hard. Oh my god, he thought, these feel amazing. He laid back in bed and pulled up a site to watch porn and jerk his sheathed shaft. Blowjobs was typed into the search bar and he clicked on a milf sucking off her man. He watched that one for a minute and clicked out to see his others options. He noticed a video with a chick in panties giving head. That's the one. As the video started Dave realized it was a crossdresser in a wig and makeup. But something about it made him stroke even faster. He kept watching and jerking. The feeling was so intensely good that he couldn't stop stroking.

As Mike was walking up to Dave's house, the dog nosed open the door and went inside. Mike got to the open door and walked in without much thought, he'd been there plenty of times. He walked through the main hall into the open plan house, but didn't see Dave. He started towards the master bedroom and was going to call for him when he heard what sounded like porn. Mike eased towards the open door and looked in. He saw Dave wearing sissy panties jerking off watching shemale porn! Mike couldn't believe it and felt his dick starting to twitch. He raised his phone and hit record. This was the hottest thing he'd seen in awhile.

Dave was stroking his sheath enclosed cock loving the smoothness and taboo of it all. As the dick in the video started cumming in the crossdressers mouth Dave blew his load. Holy fuck that was intense he thought. He was relaxing in the afterglow running his hands slowly over his silk panties when he heard, "That was hot as shit". Dave jumped up quickly scared to death and looked over and saw Mike.

"What the fuck! Get the hell out of here!"

Mike held up his phone, "Not until you help me out with this." as he pointed to his crotch. "I recorded you in those sissy panties and have sent the video to a secure site. You don't want to explain yourself to family, friends, and workers do you? "

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Dave was shaking mad, he was going to beat the shit out of Mike. That little fucking piece of shit. Then he realized that Mike could still send the video and have him arrested for assault. The fucker was some sort of computer wizard, he knew he'd never find that video. FUCK!! "Listen, I'll do anything else man. Come on we've been friends for years"

"Dave, I know you don't care for me. I've been jealous of you since we met, you are everything I wish I could be. But I'm not a sissy boy, so I have that going for me. This is the only thing I want from you. Trust me, I'd hate it for our wives, but it would tickle me pink for everyone to see who you really are, a panty wearing pervert."

Dave couldn't believe this. He stood there dumbfounded as Mike took of his shorts. "Okay, fine I'll do this, but take that phone in the other room. Don't need you recording this too." Mike put the phone away and got on the bed with his head propped up on a pillow. Dave pleaded again, "Fuck man, come on. You're kidding right?"

"No, I'm not. I haven't had sex in over a month. Haven't even jerked off in a month. I need release now. From you."

Dave moved over between his legs and finally looked down at Mike's penis. It looked barley to be 3 maybe 4 inches and thin. He couldn't believe he had to suck off this pencil dicked dork. He bent down and took it in his mouth. How the fuck did this happen. He was minding his own business masturbating in some panties, that's all. He didn't deserve this. He was a good member of society, good husband, father, worker. He'd always been nice to Mike and had never done anything to him. A tear was running down his face.

"Hey, stop crying and start sucking". Dave shut his eyes and started bobbing.

Dave had smoked bigger cigars than this guys dick. He tried to blank out his mind and to get this over with as fast as possible. He knew what he liked and started sucking and twirling his tongue around the tiny penis. Bobbing, sucking, licking, twirling.

Mike thought this might be the best blowjob of his life. Dave was sucking him off like a pro. Mike was watching him bob his head on his cock and watching Dave's dick in that sheath. Dave had just come, but Mike noticed Dave's dick was starting to grow and stretch out the nylon again. He couldn't take his eyes off that sheath wondering how it felt. After about 6-7 minutes Mike couldn't take it anymore. "Oh shit" he hissed and then let loose with a torrid of shots in Dave's mouth.

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Dave had done a good job of disconnecting his mind from what he was doing. He vaguely heard something and then his mouth started flooding with cum. He was still bobbing his head and began swallowing without realizing what was actually happening. It dawned on him after the fourth or fifth shot that he was swallowing a mans cum. Quick thoughts went through his head, mainly thinking this isn't that bad, how come my wife acts like its acid hitting her mouth. The taste wasn't great but it wasn't disgusting. He kept bobbing and swallowing.

Finally after 9 shots Mike was spent. He might have a below average penis, but he can spew a cumshot like a top notch pornstar. He never took his eyes off Dave and even after he finished Dave was still sucking. Dave eventually stopped and sat up with a dazed look in his eyes. Mike leaned back content, best blowjob and first time someone had ever swallowed his whole load.

Dave looked at Mike. Mike's eyes were closed his with a smile on his face. Dave couldn't believe he just gave a blowjob and swallowed a load of cum. He knew he had an erection and was ashamed of himself. He looked down at the huge bulge in that sheath and looked at Mike's smug face. Dave swiftly straddled Mike's chest and said "Open up bitch, one turn deserves another"

Mike's eyes got wide, "What? That's not the deal". He tried to get up but Dave was too strong. A rock hard sheath covered penis was in his face. "I'm not doing it, let me up or I'm sending that video!"

Dave had had enough. His anger took over. He reached down and grabbed a knot of Mike's hair and slammed his head against the headboard. "Open. Up." Mike looked terrified and opened his mouth. Dave shoved his cock in to the hilt. "This is what a real cock looks like you bitch!" Dave face fucked him for twenty or thirty seconds and slowed his pace to almost a stand still. Mike's head started moving back and forth with no prompting. Dave was now in control. He looked over and saw his phone laying in the bed. Mike continued sucking and Dave was loving the feeling of being in those silk panties. A sheath covered blowjob was better than he imagined. It took Mike longer to finish the job, but finish it he did. Dave grunted and unloaded in Mike's mouth. He knew his load was nowhere close to the one he swallowed. Between cumming earlier and the sheath containing some of the spunk, not nearly as much went into Mike's mouth. But, he felt somewhat vindicated.

Dave let Mike up. Mike got off the bed, grabbed his clothes and left. Not a word was spoken. An hour later Dave sent Mike a text. It was a screen shot of Mike's mouth around a sheath covered penis. Caption said "Mexican Standoff."

Mike replied back, "Agreed." Then a few minutes later Mike texted again. "The wife will be out of town Saturday if you want to come over. Noticed you had 2nd pair of panties on the bed, was thinking you could bring them both."

Dave replied, "See you then."

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