Second Meeting with a Surprise

Jack Bucky helped me again editing this story. Thank you very much!

Sam was a young man in his twenties. He had a little sexual experience but wasn't that good with women. In one forum on the internet, he had met a couple that were searching for a young man for fun. They didn't want any man-to-man action, just some enjoyment for the lady.

Sam was very nervous but went to meet the couple. They were relaxed and nice. The woman gave him nice oral and they fucked. It was a nice meeting, and the woman had good orgasms, but Sam felt so much pressure in his head that he couldn't have any orgasms. Although everything felt good, he just couldn't relax and enjoy the moment without overthinking everything. The couple was very understanding, and when Sam was leaving, they invited him to visit again sometime and try again.

This new situation was not the only thing that had made Sam nervous. The couple had wanted everything to happen bareback, and Sam didn't know if he was safe from diseases. The couple said that they had only a few sex partners with whom they had sex and that they were all clean. When he received a new invitation to come to their place, Sam didn't know what to answer -- so he didn't answer immediately. The couple seemed to understand and sent him another message where they told him that the man wouldn't be there this time if that was what made Sam nervous the first time.

Sam wondered what to do. He didn't have many opportunities to have sex with women, and the pressure for him to have some was huge. He finally answered the couple and told them that the meeting would be okay for him.

They set it up for the very same evening, and when Sam was driving there he had a message. The woman in the couple asked if it would be okay with Sam if some of her friends joined them. She told him that one of her friends is a very special lady who also likes young inexperienced men and that after this evening, Sam would be a lot more experienced.

Sam thought that just meeting the familiar MILF lady in the couple would have been better because he wouldn't have been so nervous this time around. But since Sam was already on his way and had a bulging erection in his pants, he responded by telling the lady it was all okay with him.

When he arrived at the location for the session, he parked in the familiar yard and walked to the door. The lady of the house opened it when he knocked, and she guided Sam in and gave him a warm hug. She was about 165cm (5' 4") and had nice B-cup tits, blonde hair, and an average build. Sam's eyes, however, focused on the new lady sitting on the sofa.

She was taller than Sam -- who was only 172cm (5'6") -- and she was maybe about 180cm (5'9") tall. She had a great body with C-cup breasts, a slim waist, and an athletic build. Her legs were long, lean, and covered with skintight leather-look brown leggings. She looked stunning and had a wicked smile when her eyes pierced Sam's.

"This young man is Sam and the lady on the sofa is Erica", the MILF said as she introduced them to each other.

"Hi, Sam. Come and sit next to me," Erica said with a slightly sexual smile.

Sam sat on the sofa but was ordered to sit close to Erica so that Annika the MILF would also have room on that same sofa.

It was a tight fit for Sam between the two ladies. He felt their legs against his own, and Erica's leggings felt especially nice to Sam when pressing against him. He wondered if Erica was a little younger than Annika, who was maybe in her fifties. Erica looked to be somewhere in her forties.

Annika put her hand on Sam's left leg while Erica rubbed his right leg. Sam felt the redness growing on his face.

"Don't be nervous. Let's have a nice, relaxed time together. There's no pressure and no need to hurry," Annika told him.

Erica wanted to be clear, telling Sam that, "There's always going to be a little pressure, and that's why you have to learn to relax. But don't worry -- you will learn it sooner or later." Erica then gave Sam her wicked smile and slid her hand on his leg and closer to his man parts.

"Don't tease him too much," Annika said with a smile.

"Sorry, he is so cute that I have problems keeping my hands away," Erica said seductively.

Then Erica pressed her lips against Sam's lips and gave him a very confident kiss. Next, she kissed Annika and soon they were taking turns kissing each other. Sam felt a hand squeezing his package when kissing Annika and his cock jumped to an erection.

"Let's move this to the bedroom," Annika said, and Erica agreed: "I thought that right when he walked in."

When they all got to the bedroom, everything started to go fast. Sam didn't know how it happened, but all of a sudden he didn't have any clothes on. He was standing next to the bed when Annika hugged him tightly and gave him passionate kisses with her tongue. Erica was behind him and was also pressing her body tightly against his back and kissing his neck and ears. One hand was on Sam's cock and the other was sliding upwards on Sam's leg.

,

All this was almost too much for Sam, but the women didn't stop. Sam felt Annika's hands on his buttocks, pulling them apart while they were kissing. At the same time, Erica's fingers slid up his leg and through the canyon between his buttocks.

Sam jumped a little bit and sighed.

"Someone seems to like being touched there," Erica said, and she lowered herself so that her face was on the same level as Sam's ass. Annika the MILF lowered herself too and soon had Sam's penis in her mouth. The feeling was familiar from the first meeting, but what Erica did was not familiar to Sam at all.

He felt Erica pull his buttocks apart and then her tongue touched his ass crack, slowly making its way to the rosebud, which made Sam sigh again.

He thought it felt amazing when at the same time, Annika was sucking his cock. He felt he might come soon if they didn't stop.

They noticed that too, and both of them rose.

Annika said to Sam: "Go lay on the bed on your back and I will teach you how to eat cunt."

That dirty talk worked very well for Sam. The nice Annika was who he met the first time he saw her, but now, she was also the dirty Annika and a lot more dominant.

Annika the MILF placed herself above Sam in the 69 position. Her legs locked Sam's hands below them, but instead of starting to suck again, she sat on Sam's face, rubbing her cunt against his lips and mouth.

"Suck and lick that cunt!" Annika ordered.

Sam did his best, licking her lips and trying to suck her clit. Annika moved so that Sam's tongue was placed where Annika wanted, and by doing that he was able to go from the lips to her clit. From time to time, even her anus was on Sam's face.

"Slide that tongue inside my holes!" Annika instructed and Sam did his best. Her pussy was very wet, making Sam's whole face not only wet but slick too.

Next, it was her rosebud's turn, and that was something that Sam had never done. Annika's hole was very tight and he had to use his tongue muscles to penetrate it.

It felt hot and dirty mentally for Sam, and he felt very submissive to Annika in that position.

All of the action with Annika had Sam's full attention, so he didn't notice that Erica hadn't been participating. Only when he felt naked legs parting his legs did he understand that Erica had taken her clothes off and was now getting into the action.

Sam felt her hands on his cock. They felt different but good.

"I noticed how you were looking at my pants and I recognized leather fetishism in your eyes," Erica said. "I bet that you also like the touch of my leather gloves." Erica slid her gloved hand on the underside of Sam's penis. Her other hand rubbed between his legs, between his buttocks, and against his anus. When her fingers rubbed his hole, her other hand massaged his balls and the skin between the hole and balls.

Erica was only touching the tip of his penis, collecting the precum that Sam was producing a lot of. She then slid her fingers under Annika the MILF's buttocks and directly into Sam's mouth. Erica made him lick and suck his precum from her leather gloves.

Then, Erica's hands were gone, so Sam concentrated on pleasuring Annika.

He also heard some squeaking sounds, almost like someone was putting on examination gloves.

Annika was near orgasm and was pressing her vulva against Sam's mouth. When she reached the top and orgasmed, she squirted all over Sam's face. At the same moment, Sam felt Erica's hands again but this time they felt again different. They didn't feel like leather gloves or bare skin. They were very slick and took hold of his penis, and then Sam felt a slick finger on his anus and it slipped in with a fast move.

Sam sighed again from surprise and the feeling. It hurt a little but also felt very nice.

Sam didn't see anything. Annika was still pressing her vulva against his face while she was in her post-orgasmic state.

"It's so tight, but still a little bit hungry ass I would say," Erica said with a husky voice.

"Feels so nice on my finger. Let's see how many you can take" she says, and with a slow move, she adds a second finger and presses them against Sam's prostate.

These are all new experiences for Sam. He has never tried anything anal. He watched some porn where women used men's asses, and that turned him on. One time he accidentally clicked on a video where a T-girl was penetrating a man but that was too much for him and he closed that video fast. Afterward, he thought about it many times.

Now he is experiencing it firsthand. Someone had fingers in his ass and it was starting to feel nice.

Erica noticed that too and started to add a third finger. It hurt but Sam could take it.

"Looks so hot when you are giving your cute little ass to someone to use," Annika says with a husky voice. She had recovered from her orgasm but was still sitting on Sam's face so that he could see what Erica was doing.

When Sam adapted to the three fingers Erica took them out and said: "I don't want to stretch your anus more with my fingers."

She rose from the bed, taking the gloves off. Sam thought that she was just going to put them in the trash.

Annika sat up as she slid off Sam's face and said: "Your tool looks so hard now that I want it inside!"

With that, she went on her back and pointed Sam to come between her legs.

Sam did that and slid his cock into Annika's slick and warm pussy.

When he was completely in, Annika crossed her legs around Sam's waist and pressed him closer to her.

"Let's take this slowly," Annika said. "Come very close and hug me. Put your head beside my head and keep still." She said this with a very comforting and calm voice.

Sam did that and Annika whispered in his ear: " Whatever happens don't be mad at me. Some things can hurt a little and some things can hurt a lot, but I promise that in the end, everything will feel better than anything you have felt before."

As she said that she crossed her hands around Sam and gave him a tight hug. At the same time, Sam noticed that Erica had come back to the bed and was behind him. She had new pair of exam gloves on her hands but she was not touching Sam's ass with them. The other hand went over Sam's mouth tightly and the other one did something between her legs. Sam could see it there.

"Look me in the eyes," Annika said in a very excited voice.

When Sam turns his eyes to Annika he feels something new on his anus. It is bigger than the finger and it is hard and warm. Instantly it starts to penetrate Sam's rosebud. It hurts Sam a lot. The tightly gripping gloved hand muffles his cries and his tears drop on those black vinyl gloves.

"Sorry that I did this to you but I promise that the pain will be over at some point," Annika said while comforting Sam as she looked into his eyes.

"It is just so exciting to see a young man's virginity get taken from his ass by a woman that has a big hard cock," Annika says to Sam, looking into his eyes, seeing that the young man understands what is going in his ass and spreading it wider than ever.

"He is so tight and his ass is squeezing my cock so good!" Erica says.

"Take it slowly, please!" Annika the MILF tells Erica.

Sam didn't say anything. He just looked in great pain. These women had set a trap for him and he walked right into it. Now a big cock was going into his ass and taking his cherry. Another woman was taking a strong hold of him and keeping him still for a Trans woman who was taking her joy from his ass -- and that ass would never be the same ever again.

Erica pressed her cock in slowly but never stopped, and soon Sam felt her hips push up against his buttocks. Her cock was so big it felt like it was in his stomach.

Erica stayed still in his ass for 10 seconds, then slowly drew it out completely. Sam suddenly feels that his anus is gaping.

"Now it is easier to lube," Erica says and presses a big applicator of lube into Sam's anus.

Then the big penis is at Sam's entrance and he feels it sliding in again. Now it goes a little bit faster. The pain is still there, but Erica seems to be taking her enjoyment anyway. Sam's cries are muffled with her strong gloved hand and Annika is surprisingly strong as she keeps him in place.

With long and steady strokes, Erica starts to really fuck Sam. The pain is there but it has eased up somewhat and is not that strong now.

"You remember when I told you that today you will learn to relax also under pressure? Now you are under me and great pressure is filling your cute little butt. It would be a good time to also learn to relax," Erica says to Sam with a wicked smile.

"I'm going to fuck your bottom until I fill it with my juices that you will feel deep in your ass before they start dripping from your little rosebud -- which will not be that small when I am done with you," Erica adds.

Sam knows that he should try to relax as much as possible. To his surprise, he notices that his cock is still hard and maybe harder than ever. The pain hasn't taken the erection away. He has enjoyed the moment, it seems. Having two women dominating him made him fall into the subspace. He also felt Annika gripping his cock with her pussy and how that pussy was massaging him. That took his mind off the pain and he manages to relax a bit. As he did that, Erica moves her hand away from Sam's mouth, grabbed hold of his hips, and started to fuck him very forcefully. Sam just moaned. He was in a state that he could not resist. And now the hard fucking was driving the growing feeling that made him want more.

All of a sudden, all three of them were moaning. Annika the MILF's pussy started gripping Sam hard and that made him come like a volcano. The pussy pumping and the cock massaging his prostate had done the job. Sam's ass gripped Erica's cock forcefully in orgasm as she was fucking his ass incredibly fast. Then Erica stopped when she completely hit bottom, and with some loud moans, she filled Sam with her juices.

They all collapsed into a pile and stayed there for a few moments. Then they rose, and both women hugged Sam. He didn't know if he should be mad or grateful.

"You must be very confused about what just happened," Erica said. "Please know that everything is okay and the world is still the same. You do not have your butt cherry anymore, but I promise that I keep in my soul what you gave to me, just like I do with all the virgins I have taken. You might even forget the details from this meeting, but don't worry, I took photos and videos of the best parts of our meeting. We can watch them together any time you want. Now put your clothes on and drive home safely as you feel my juices dripping from your bum." As Erica says that, she stops and gives Sam a kiss.

"You were brave and you gave me great pleasure when I was able to watch up close what happened to you," Annika the MILF says. "I hope that you are not mad and come to visit us again. It was nice that you also orgasmed this time," she adds in a teasing tone.

Sam went home but his ass hurt for days. It also dripped Erica's juices much longer than he thought it would. But when it stopped hurting, he started thinking that he wanted more of her inside him.

Then out of the blue, a new invitation with a picture of Erica's big cock sliding into Sam's ass popped up on his phone. He didn't think twice about it; he just quickly texted back, "I'm coming."