“When is he due back?”

“Who?”

Audrey gave Jill a look. “Oh, you mean Jack? Not sure actually.”

“I call that bullshit. You know exactly when he will be back.”

Jill smiled dreamily . “Yeah, tomorrow at 8.15pm.”

“And by 9.30pm you will have his cock deep inside you?”

“Hopefully.”

“How long has he been gone?”

“Three months almost, hiking in South America with his other macho friends.”

Audrey thought about her friend’s fuck buddy. Jack was such a man’s man. Tall, broad shoulders, square jaw and thick dark brown hair and piercing green eyes. He was a real catch in the looks department, but sadly his attitude towards women and relationships needed massive improvement. Jill was not in love with him, but they had a good sex relationship which meant they got together a few times a month. After, she would call her best friend Audrey and tell her all about it.

What Jack didn’t know and would probably get an instant erection from, was that Jill and Audrey also were fuck buddies. At 25 and 27 they had both realized that they were curious about bisexuality and one evening after a few bottles of wine, Audrey who was the older had simply kissed Jill. It ended in a long night of wild sex and the next morning they both woke up with hangovers, but giggling happily from having taken the leap and tried it out. Since then they met up whenever they could and spent time together in bed.

Jill leaned in and sucked on Audrey’s erect nipple for a bit and then said, “I hope you aren’t jealous?”

“Not at all, what we have is different from what you have with Jack, and I’m fine with it.”

“Thanks.”

Audrey gently pushed Jill’s head downwards until her lips touched her shaved pussy. Even though she had come twice already Audrey could never get enough. Her curvy 5.7 body ached for sex whenever she could and her slightly taller friend was happy to help. She watched Jill gently nibbled on her swollen lips and then began to suck and lick her clit. Audrey lay back and let the orgasm wash over her and when she relaxed, Jill straddled her, so her pussy was just above Audrey’s face. Looking down, she said, “You know what to do.”

And Audrey did and loved every moment of it. Especially when Jill came in a squirting orgasm, which only happened when she was really horny, like now.

oOo

Jill hardly recognized Jack when he walked into the arrival hall at the airport. He said a quick goodbye to his friends and then he saw her. He had left clean shaven, and not a body hair on him. Even though he was an alpha male he loved to be shaved all over. The man that walked towards her with a grin on his face had a thick beard, his hair was in a pony tail and Jill suspected he had a wild afro between his legs.

“Baby, you look so hot!” he said and slapped her bum. Typical, she thought.

She wore a short dress that showed off her long legs and gave her boobs some extra cleavage. He walked ahead and she followed.

When they reach the car and sat down, he slid a hand onto her thigh and then down to her pussy.

“Yes! No panties, I love it.”

It was a short but difficult drive back to Jack’s place because he kept on finger fucking her all the way. When she got out there was a wet spot on the seat.

Inside he tore off her dress and then bent her over the sofa armrest. His cock impaled her and then he fucked her hard and shot his load over her lower back. That was Jack’s way of fucking. Not that she she did not enjoy it, but she wanted more foreplay more of a warming up.

She knelt before him and then sucked the last drops of cum out of his still hard dick. To her surprise he came again, and as always she swallowed like a good girl.

“Fuck, that was good. Listen, I gonna take a quick shower and the head out with the guys. I’ll call you later in the week.”

Jill was left alone in the living room, cum on her back and on her chin. Asshole, she thought, but at the same time she was so glad he was alright and back home again.

oOo

A couple of days late, Jill and Audrey met up for dinner. They had chosen a family owned bistro that was between where they lived. Close enough to walk to so they could have some wine with their dinner. It was a warm evening and as Jill walked along the sidewalk she thought she saw Jack come down the other side of the street. She was about to call out to him when he stopped at a shop window. She knew it, it was a shop that sold sexy and very expensive lingerie. She smiled to herself, what a thoughtful guy. Jack went inside and after a few minutes came back out with a bag in his hand. Jill continued to the restaurant, sure that Jack would surprise her next time they met which was the following weekend. Only three days away, but to Jill it felt like a month.

“Hi, what took you so long?” Audrey said.

“I saw Jack, he was buying me some sexy underwear.”

Audrey tilted her head. “Has he done that before?”

“No, that’s why I’m so excited.”

“Hm, I don’t want to be an asshole, but what if it’s for another woman?”

Jill indicated with her hand to the waiter that she wanted the same drink as Jill. “Doubt it, you know how he is.”

“Still, he could charm some innocent teen girl.”

“True, but he likes his women in their twenties. He told me that once.”

Her drink arrived and Jill tasted the Gin and Tonic before continuing. “Anyway, we will see each other this weekend and then I will find out if he bought it for me.”

Audrey sighed. “I hope you don’t get hurt.”

Over dinner they talked about their jobs, shitty co-workers and bosses. When their coffees had arrived Audrey leaned in over the table and said in a quiet voice, “Do you know what a Sissygasm is?”

“No, and why are you whispering?”

“Because it’s when a dude shoots his load without using his hands or anyone else’s.”

“How does that work, and why are we even talking about that subject, eww?”

“I read it on this sexual forum I follow. I had no clue such a thing was even possible.”

“Well, think about the gay and bisexual guys, they must get off doing it in their asses.”

Audrey sat back and drank from her cup, always using two hands. “Maybe you are right.”

“I like using my hands and mouth.”

“Sure, but think about it, what a power trip it would be to be able to make a guy come without using them.”

They agreed it would and that it would be a fun thing to try some time. They both enjoyed anal sex whenever it was done right, so the idea of giving it to a man wasn’t far-fetched.

oOo

Jill almost giggled when she knocked on Jack’s door. It was Saturday afternoon and the sun was hot on her bare back. She wore a white armless summer dress, heels and as usual no underwear. Jack opened the door and let her in. This time he didn’t fuck her right away. Instead, he offered her a glass of wine and then they sat on the sofa watching the photos he had taken on his trip on his large LED screen.

“So, did you fuck any hot latina women on your trip?” she asked when the show was over.

“Honestly, no. We spent so much time in the jungles and there the local chicks aren’t exactly my type. Even though some are topless they are short and squat with saggy tits.” He put an arm around her shoulder and gently squeezed her right boob. “Not firm like yours, honey.”

They kissed deeply and while they did Jill wondered when he would give her the gift. Maybe after they had had sex? The thought vanished as Jack slid down on the floor and then began to lick her newly shaved pussy. When she came, she grabbed the armrest so hard her knuckles turned white.

Standing up Jack opened his pants and let them fall to the floor. He had no underwear on and his shaved cock stood straight up. He had quite a large cockhead and Jill loved to suck on it which she did, tasting the pre-cum that soon began to ooze out. She cupped his balls and teased them with her nails until Jack moaned loudly.

He lifted her up and lay her down on the coffee table with her legs over his shoulders. He entered her fast and hard which made her yelp but after that it was glorious orgasm after orgasm until she lay like a wet rag on the table. Jack looked down at her.

“You got to have the best pussy in town, Jill. I need to go to the store, but you are welcome to take a shower before you go.”

Jill heard the front door close and he was gone. She slowly got up. Jack was funny in the sense he never fucked on his bed, only around the house. When they did it at her place, they used her bed. When she walked to the bathroom, she noticed the door to his bed room was slightly open and she couldn’t resist the curiosity. It was neat and smelled of incense. When did Jack become an incense guy, she wondered? The bed was made and there was no clutter at all. A drawer was slightly ajar and when she peeked inside, she put her hand to her mouth in shock. It was filled with panties. Cotton, lace, leather, thongs, bikinis, briefs and strings. She opened it a bit more and behind the panties were garter belts and stockings. This was so weird, she thought. Were they trophies from previous women, maybe?”

She went over to the large wardrobe and opened it. Jack liked clothes and spent a substantial amount each month. There were rows of suits, shirts, jeans, and sweaters. Below them rows of shoes. She took out a suit and smelled the collar. No fragrance of a woman. She tried a few more, but nothing. At the very end to the right was a black Armani suit. She checked that, but nothing. As she was about to put it back, she saw some colour behind it and pushed the other suits to the side.

Another rod was behind the one with the suits, but this one had dresses on it. Long, short, and many colours. Also a few skirts, and blouses hung among them. Again, Jill smelled a few, but no female fragrance, not even a hint. She put everything back as it was and went to the bathroom. In the shower she tried to figure out what was going on but couldn’t.

oOo

A few days later, Jill and Audrey were lying in Audrey's bed. A 24-inch double ended dong lay between them, still glittering from their pussy juices. Jill had bought it for her friend and they often used it. Mostly in a doggy position so their ass cheeks rubbed against each other as they fucked.

“So, what are you going to do, confront him?” asked Audrey while caressing Jill’s left boob.

“No, I’m going to see if he confesses to the other girls.” She grabbed her phone that was on the nightstand and sent Jack a text.

A few minutes later he wrote back. Jill read it and got up.

“What’s he saying?” Audrey said while stretching like a cat.

“We are meeting for drinks in an hour. I just said I wanted to hang out.”

“Cool, I hope it works out.”

Jack was waiting for her when she walked into the bar. He kissed her cheek and ordered her a glass of wine.

“What’s up babe?”

She took a deep breath. “We have been fucking for over a year now and I think we can be honest with each other, right?”

He nodded.

“So, I have a confession to make, and I want you to tell me any secrets you have.”

Jack leaned in; his eyes showed no emotions.

“Okay, just so you know, Audrey and I are sleeping together.”

He looked at her like he hadn’t quite understood the words and then burst into a laugh. “I knew it, that is so fucking cool. I’d love to join in.”

“Maybe, I’ll talk to her about that. Anyway, do you have something you want to share?”

Jack thought for a moment and then took a drink from his beer.

“Nope, nothing. I’m an open book, no secrets at all.”

Shit, thought Jill. It hadn’t worked. She couldn’t tell him what she had found since that meant she would confess to snooping around his place. Then she had an idea.“Look, the other day I saw you go into that lingerie shop on West 23 street.”

Jack played it cool. “Yeah, I was there.”

“Doing what?”

“I bought a sexy panty.”

“For who?”

“You, it’s your birthday in two weeks. They had one on sale, so I bought it.”

Jill felt so stupid. How could she ever had doubted him?

“Sorry, Jack, that is so sweet of you.”

“It’s okay, but you yourself spoiled the surprise.”

Jill drank from her wine and ordered another. “Yes, I did.”

“Now, tell me all about the hot stuff you and Audrey get up to.”

oOo

“Are you ready for this?” Asked Jill when she and Audrey walked up the stairs to Jack’s second floor apartment.

“Yes, I think so. It’s not that I haven’t had cock before, you know I have had plenty. But I have never had a threesome before.”

“Neither have I, so we will learn something new together.”

Jack opened the door and invited them in. In the living room he had put out snacks and a couple of bottles of white wine. The three ate and drank to get comfortable. Jill didn’t mention what she had found, but noted that Jack was eyeing Audrey a lot.

“Jack, do you like Audrey?” she asked.

“Yes, she is so hot.”

“Thanks, that’s nice of you,” said Audrey and smiled.

Jill slowly used her left hand to push up Audrey’s skirt and her friend spread her legs a little and slid further down on the sofa. Jack’s eyes widened as he saw Audrey’s pussy.

“Isn’t it cute, just like a teen’s,” Jill purred.

Audrey slid a finger along the slit and then pushed her middle finger inside herself. “Mm, it’s so hot and wet.”

Jack licked his lips and looked like a starving wolf ready to pounce on his prey. Audrey closed her eyes and continued playing with herself and then suddenly stopped. “I need to use the bathroom.”

She closed the door after her and then looked around. Just like Jill had told her there was a wicker basket with dirty laundry next to the washing machine. She began to pull boxer shorts, socks and shirts from it and half way down, she found what she was looking for. A black lace thong. She smiled as she walked out, now they got him.

“So, Jack, have you had a visitor?” she asked while spinning the thong in the air with her fingers.

For the first time since she had met Jack, Jill saw him blush and look uncomfortable. The horny wolf was gone and had been replaced by a school boy who had been caught with his hand in the cookie jar.

“I can explain.”

Audrey sat down next to Jill, still twirling the panty. “We are all ears, go ahead.”

He cleared his throat and then turned his green eyes to Jill. “I do have a confession to make, but it has nothing to do with other women, I promise. Even though we are just fuck buddies I still respect you and would be honest if I did fuck someone else.”

“Just spit it out, Jack,” said Jill.

“Okay, the fact is, I like to dress like a girl.”

There was a long silence in the room. Audrey dropped the thong and didn’t pick it up. After a while she asked, “You do what?”

“I put on panties, a dress, even a wig sometimes and I wear it here at home. It makes me feel good.”

“Holy shit, we have ourselves a real Sissy, Jill! Just like I read about on the forum.”

“I can’t believe it, Jack. When did all this start?” Jill asked.

“When I was a teenager. I used my sister's panties in secret and then I would jerk off.”

“But...but, look at you, you are such a macho.”

Jack laughed. “Maybe, but I like to feel like a girl, sometimes.”

“I’m not judging you, and I think it’s great that you have this little thing going on. But I had hoped you would have trusted me and told me earlier.”

“I wasn’t sure how you would take it. Some people think it's weird, even sick.”

Audrey picked up the panty and put it on the table. “I think it’s kind of cute. Would you mind showing us?”

“What do you mean?”

“Go and dress up like a girl.”

“Why?”

Audrey looked at Jill, who nodded. “Because we want to see how pretty you are.”

Jack slowly got up. “Fine, but if you laugh at me, then you can get the fuck out.”

The two girls shook their heads and watched him close the door to his bed room behind him.

“Holy shit, I had no idea,” whispered Jill.

“You know what this means?”

“No?”

Audrey went over to where she had left her large purse and when she came back, she was holding one of their vibrators in her hand. She wiggled it. “Sissygasm.”

Jill giggled. “I hope he plays along.”

They sat talking and drinking for about half an hour before the bed room door opened and Jack stepped out.

Their jaws dropped and Jill said, “Holy shit, that is amazing.”

He walked towards them on four-inch heels, a red flared skirt that ended above his knees. He wore a white blouse and his face had makeup and the long brown hair of the wig hung across his left eye.

“That’s pretty impressive,” said Audrey.

“What kind of panty are you wearing?” asked Jill.

He lifted the skirt. “I thought white lace would be nice.”

Through the thin fabric the girls could make out the shape of his cock. “How do you keep it in place?” Audrey asked as Jack sat down.

“I just pull the whole package as far back as I can but sometimes my nuts hang out.”

This made the girls smile and then Jill said, “I’ve got to give it to you, your makeup is amazing. How did you learn that?”

“YouTube.”

“You got to be kidding! The only place I have seen something so perfect is when the brands have a hostess demonstrating on people.”

“Thanks. So, what do you think?”

Audrey tilted her head. “You are kind of cute, but I don’t think you would pass as a woman. You have no boobs.”

“I know, I have been thinking about buying some fake ones.”

Jill’s jaw dropped. “As in a boob job?”

“No, no, silly. They are made from silicone and stuck to my chest.”

“Oh, thank goodness for that. I couldn’t stand seeing you with real tits.”

“What do you get off on?” Audrey asked.

“Well, I guess it's the smooth fabric of the lace, and the rest of the clothes. My cock goes hard as soon as I put on a pair of panties.”

“You got an erection now?”

He lifted the skirt again and they saw how his cock strained against the lace. It was unnaturally bent under his nuts.

“Why don’t you show us how cute you are in just panties,” suggested Jill.

Jack got up and took of the top and skirt. Then he turned in a circle showing them his tight ass cheeks.

“Fuck, that looks pretty hot. Come here.” Audrey said in a husky voice.

When Jack stood in front of her she let her fingers play along his shaft and in between his legs. A small moan left Jack’s lips.

“Oh, you like it?”

“Mm, feels good.”

She gently kissed his skin just above the lining of the pantie. It was smooth and she realized he was completely shaved. When she pulled away, she noted that the veins on his cock threatened to burst.

She slid her thumbs under the hem and then slowly pulled down the panties. Jack’s cock sprung out and a drop of pre-cum hit Audrey on the cheek.

Jill laughed so hard that she almost spilled her drink. “My poor man is leaking, just look at that.”

A long strain hung from the tip of his cockhead and while the girls watched with curiosity mixed excitement it broke and a drop landed on the parquet floor. Another drop soon formed on the tip. This one Audrey wiped off with the pad of her index finger. She licked it and smiled. “Tastes good. Let’s see if we can’t get some more out of you.”

She wrapped her thumb and index finger around the root of his shaft and then slowly pulled towards her. A much larger drop quickly formed and this one Jill licked off, and the next, and the next.

“God that is a lot, Jack.” Audrey said before taking a drop for herself.

“Would you call your cock your man pussy?” said Jill.

Audrey had begun to slowly stroke him and Jack closed his eyes. “I guess, or maybe my ass. I’m not sure.”

The girls exchanged a look and Jill said, “So, if we would like to fuck the pretty Sissy, how would we do that?”

Jack shuddered at her words, but didn’t open his eyes. “I guess you would have to fuck my ass.”

“Really?

“Mm, I want you to fuck my man pussy, I want to feel like a pretty girl.”

Jack couldn’t believe he had actually said those words. His eyes fluttered open and he looked down at Audrey and Jill sitting on the sofa. They were both rubbing their pussies and while he watched Jill stuck a finger inside herself and a wet sound filled the room. He had felt embarrassed walking out dressed as a girl, but it had soon gone away. The girls were nice to him and apparently were turned on by the entire experience. He had never thought about having sex while dressed as a woman, it was just something he did at home before jerking off.

Now the opportunity was sitting right in front of him. Being with a man was nothing he would do, but being with Audrey and Jill, that was something different.

“It just so happens I brought this with me. I had thought that you might like to watch us use it on each other,” said Audrey and showed him the cock formed vibrator.

“Oh shit, that’s pretty big.”

“It’s the best internet has to offer. Eight inches of cyberskin covered vibrator, and trust me, it feels almost like the real thing.”

She handed the toy to Jack. She and Jill had stopped playing with themselves, they wanted to wait and enjoy the show first.

Jack looked at the toy in his hand. It looked so real he thought. Turning it on he felt the strong vibrations and said, “I bet you two have had a lot of fun with this.”

The girls nodded and giggled.

“So, how do we do this?”

“I guess we need lube and a bed,” said Jill.

Jack lead the way to the bed room and the girls stared at his round ass. Jill had seen it before, but Audrey was impressed by the round form, almost like a girl's.

From a drawer in his nightstand Jack took out a tube of lube and handed it to Jill. “I want you to do it.”

“Okay, I guess you need to be in a doggy position.”

When Jack was on all fours on the bed Audrey had an idea. “I want to drink his pre-cum and cum.”

She got on the bed and lay down between his legs. With a bit of wiggling she ended up just under his cock.

“Ready?” asked Jill.

At first it was more like a tickle, thought Jack. The tip of the vibrator was pressed against his anus, and the sensation from the vibrations sent waves of pleasure through his body. Jill used a bit more force and his anus began to open, a completely new experience for him.

“This might sound weird, but if you if you push like when you go to the toilet, it’s easier. That’s what I do,” said Jill matter of factly.

Jack followed her advice and as he did the vibrator slid in an inch or so. At the same time his entire body began to react to the vibrations. His legs began to quiver, his breath became shorter and his cock strangely enough went limp.

“Oh my god, what did you do?” Asked Audrey.

“Why, what happened?”

“His cock is like all flaccid but loads of pre-cum is dripping out, not a drop at a time but constantly.”

Jill pushed a bit more and it was as if Jack’s sphincter had stopped working, the entire eight inches slid in.

“Oh, wow, fuck me, that is intense,” moaned Jack.

He looked between his legs and Audrey lay with her mouth open, letting the pre-cum drip right into her mouth. He felt like if he was urinating the stuff, so much was coming out of him.

Then an entirely new emotion hit him. He was being fucked by a woman, in his man pussy.

“Yes, yes, fuck my tight pussy, fuck me hard, Jill,” he moaned.

She did what he asked, but soon realized it was more the vibrations that made Jack feel good than shoving the toy back and forth so she just left it deep inside him.

Jack’s legs began to shake uncontrollably and he gripped the mattress hard as his body convulsed and his balls contracted several times.

Jill heard Audrey gasp and looking between Jack’s legs she saw her friend drinking cum as it came out of Jack’s cock. Not in shots, but a steady stream of it. Not only that, as his balls contracted more and more came out, it must have been several tablespoons, she figured.

Gently she pulled the toy out at the same time as Audrey wiggled out from under Jack. She wiped a bit of cum from her chin. “Girl, that was impressive. I have never seen a man shooting that much cum.”

“He didn’t shoot, it just ran out of him,” corrected Jill.

“Doesn’t matter, it was amazing anyway.”

They both turned to Jack, who had rolled over onto his back. “So, sissyboy, how did you like your first Sissygasm?”

Jack grinned at them. “I loved it, and want more, but now, I want some tight pussy around my cock and on my face.”

Jill noted his cock being hard again, just the way she liked it. She straddled him and slowly sat down, bathing in the sensations of being filled by him. Audrey straddled his face so she was facing Jill and the girls kissed each other.

“Wow, that is so sexy,” moaned Jack as Jill began to ride him slowly.”

“One of these days we will fuck you with strap-ons so you can get your ass filled and suck cock at the same time. Would you like that, Sissy?” asked Audrey, rubbing her pussy over his face.

“Yes! Just the thought makes me wanna come.”

“No, no, not yet, you need to fuck both of us, we have earned it.”

They laughed and then the room filled with the wet sounds of good fucking.