Christmas Bachelor Auction Pt. 02

He stands in front of mom and reaches around to undo the clasps. All three clasps are set free and the bra is loose. He pulls the bra free from the front and her large breasts fall out. Nature takes over and they sag some. They are huge. Big puffy blobs of joy. Anthony eagerly grabs a breast and brings it up to his mouth where he devours it. No fingers, just alternate between the two breasts, sucking on the huge nipples that are rock hard.

Mom is the first to orgasm. She would have collapsed but Anthony is holding her, anticipating that would happen. He sat her in a chair while he continues to feast. She quickly orgasms a second time. Anthony is proud of himself as I was of him.

Mom rolls a 4 and drew a card for me and Anthony because Anthony was also on the same space.

Mom read a card for me, "Your target is an ass man, he loves women's asses. Let's see how he likes it. Use anal beads on your target."

Mom looked through the box and found a long set of anal beads. Oh shit. She grinned at me and got the lube. She bent me over the table and lubed me up, even sticking a finger in me to make sure I was ready. She was evilly slow at inserting the increasingly large beads into my ass one at a time. Everyone gathered to get a good look as they went in. My sphincter hurt but once inside it was an odd sensation. It didn't do much for me inside.

I guess the real show was watching them go in and out and that I missed. When she finished two insertions and extractions, that was it, she washed her hands and me of the lube. Can't say I enjoyed that.

Now she read Anthony's card, "This stud is all man and hard as steel, let us bring him to his knees. Use a tickler on your target."

Mom learned from me and did the same thing to Anthony as I did earlier. He hates tickles, but let mom have her way with him.

Donna rolls a 5 and draws a card.

Donna reads, "Your target has been a good sport tonight, give him a kiss to show how much you care. We want to see tongues!"

Donna walks to John swaying her hips, takes him with both hands and seductively kisses him on the lips. She stayed with him, it was a real kiss, like between lovers. She opens her mouth as her tongue invades his mouth, we can see tongue and then she giggles.

She laughs, "Bill, it was just a kiss. Lighten up, I am standing naked here with your friends." I blush.

I roll a 1 and draw a card.

I read the card, "Ahhhh those fluffy white orbs. Silver dollar saucers and pebble on the tips. They are so much fun to play with. Maul the breasts of your target."

I stand behind Karen, she enjoyed my cock along her ass. I cup both breasts and squeezed them hard. They are awesome. Smallest ones here but firm and a semi-solid center. I could palm the entire breast and alternate squeezing them, causing Karen to moan. I continue until she orgasms. I already had a hold of her, so she didn't fall but I had to sit her down in a chair.

Jane took her turn, rolls a 5 and draws a card.

She read it, blushed, and then read it out loud, "You have been staring at it all night. Now is the time, give your target a blowjob. Swallow like a pro."

She looked real nervously at John.

John says to Jane, "I love you. I love Anthony like a brother. Show the little lad how wonderful you are." He gave her a reassuring smile.

Now that she had permission she looked relieved, that could have gone bad. Jane kneels in front of Anthony. She looks up into his eyes, smiles, and then slowly pulls his shorts down. She really took her time and made a show of it. Inch down on the right then an inch on the left until gravity takes over. Now his boxers have a large obstruction in the expected place.

She is quicker this time, both hands hook opposite sides of his boxers. She is slow to show him. Eventually, she pulls them down together all the way to the ground. He isn't huge, few inches shorter but a bit wider than I am.

His cock is pointing up, Jane takes it in her hand and pointed it down towards her wet and inviting mouth. She hesitates as her tongue is about to swallow his tip. She looks at him again, smiles, then slowly moves her head forward to fully engulf his entire cock. She held it a moment and then backs it out of her mouth. With a few inches to go, she stops. It looks like she is swirling her tongue around his shaft, hitting the bottom of his mushroom where it is sensitive. She bobs up and down his length twisting her neck.

Anthony is amazed, "Wow, I mean wow, this woman can suck a cock."

John laughs, "That she can. I knew you would love it. Best I ever had."

Anthony warns, "Jane baby, it isn't going to belong."

Jane redoubles her effort. She is going faster and adds suction. She releases his cock, spits on it and attacks it again with vigor. I can see the look on his face, he is struggling now to hold his load. Jane is obviously very good, he hasn't a chance to hold out against her.

Several more bobs of her head and she pulls back and opens her mouth wide just in time for us to see Anthony shoot his load into her mouth.

I announce, "Wow, that was one hell of a show. Wonderful job Jane and thank you, John, for allowing her to share that with us."

With Anthony now done, Jane audibly swallows with a smile and then attempts to clean Anthony off. Karen put her hand out as a stop sign. She got on her knees and slowing cleans Anthony off. Never seen such a seductive cleaning. She used long slow strokes of her tongue followed by swallowing his member after the licking. She then stood up with a smile.

John rolls a 2, moves two spaces, and then draws a card.

He reads the card, "Ass. Arse. Butt. Rear end. Shitter. You know the names, now it's time to ratchet up the fun for your target. Take a butt plug, add lube, then combine the device and lube into your target's arse. It remains in place for the rest of the night."

John asks my mom, "Before I select a plug, would you like to help me pick out one that meets your experience and willingness?"

Mom flippantly replies, "I have not been touched by my husband in quite a while. I still have needs and would be amazed if any of Bill's skinny ass girlfriends can take anything close to what I can. Take whatever you want."

John in a flash pulls moms shorts and panties down and off. She is now fully naked. Thicker and curvy than the younger women yet well preserved, very few wrinkles, nice smooth skin. She has a clean cunt, just a black line pointing the way. If dad ever decided to go looking, she showed him the way. Mom is 48 so not old. Her hair is out of style, her clothes are out of style. Her breasts sag some but really, for her age, usually its much worse. Overall, mom is much sexier than I ever expected. Dad is an idiot.

John bent mom down over the table and then went to the box to find a plug. I had a full training set and some that never saw use. His eyes light up, I know exactly what he found. I would have objected but mom seemed to be experienced. She could not see the item he pulled out of the box. Jane and Donna gasp when they see the item he picked out.

In his hands is a black, two-headed "snake". It is flexible, with a two-inch thick tube going from end to end. The tube part of the "snake" is about four feet long! It was huge. The two ends were different. One end, the smaller one, started out at a point and like a cone got larger until the max then immediately tapered off to just the tube. The other end was similar, the tube ran into the tip of the cone then got larger as cones do. After the cone, it tapers to a two-inch tube and then a base that was large enough to prevent going in. Nobody says a word. Mom has no clue what he pulled out.

John lubes up mom but not excessively. He has a huge smile on his face. He is thoroughly enjoying this. He takes the smaller of the two ends with the small cone tip and inserts it into mom's ass. I stand in shock at how easily it went in. That would have killed me.

Mom taunts John with a smirk on her face, "Is that the biggest you have?"

John is silent, but he continues to push the snake up into my mother. Mom is now on her haunches, she seems curious as she can feel it moving in her and must feel John continuing to push the "snake" up into her. He is past halfway, it's getting harder to get in. In my mind as an engineer, I can see the tube coiling inside of mom like a garden hose. Still, it must be going further in.

Mom inquires, "What the hell are you putting into me?"

Donna has fun with mom, "Didn't you say you were experienced? John found something interesting. Don't worry, it's over halfway in."

Mom is surprised, 'Damn, that thing is a monster. I love it. It's stuffing me like nothing else."

Mom moans.

John continues, pushing harder now. He is at the next cone. He gets about three-quarters of the way up the cone when mom grunts. She is sweating and pushing into John as he pushes forward. Finally, it pops in. Mom screams ouch and then collapses on the table. She orgasms.

We all stand around, stunned at the display. Mom stands up and lets out a moan.

Mom shudders, "This is amazing. I need me one of these. What an incredible way to go to sleep. If it's possible to sleep with this in me. Damn, I must keep this in. Oh, what a joy. I love you guys."

Karen rolls a 5 and moves to my space. She smiles.

Karen smiles cutely, "It says to draw a card and then I draw a second card and lucky me, you're the target of both. The first card says, 'Guys love seeing a woman use a strap-on, women get it in the cunt or ass, your target doesn't have a cunt so give it to him up the ass.'"

Oh fuck, why me?

Karen quickly gets a strap-on from the box. Not the biggest but not the smallest. I bend over the table at her request. John and Anthony hold me in place, how considerate of them. Karen lubes the strap-on and my ass. She inserts a finger into me to get more on the inside.

Karen is tentative, it takes a while to get in position. I lower my ass, so she can reach me easily. She starts off slowly pushing into me. It hurts. She has constant pressure. It constantly hurts. Once in, she stops for a moment. No pain. She slowly pulls out; the pain is back. I scream. She pushes back in faster.

Holy hell that hurts. With each thrust back into my rectum, my scream of pain lessens. I never did feel the joy, just pain. It did lessen but this isn't something I will ever choose to do. After a few minutes, Karen has had enough, she stops. She cleans off the strap on while I lay on the ground recovering.

Karen reads the second card, "This game can be quite stressful, your target has been through a lot, give him a massage. He only gets his front done. Happy endings are optional."

Karen rolls me onto my back. I now appreciate the choice to buy carpeting and not cold tile. She starts by giving me a light kiss on the lips, "I think you will like this a lot more and I hope it makes up for the strap-on."

I doubt that is possible, that hurt like hell, but I amuse her and smile. She starts at the top of my shoulders and rubs hard, it feels great. She makes sure her perky breasts slap my face. She didn't have to do that, she wanted to, and it was nice. I can feel Karen's wetness on my stomach where she is straddling me around my hips. She inches down and is now doing the tips of my shoulders. She inches back more and stops at my standing pole. She continues rubbing the top portion of my arms. Her ass crack is wrapping around my cock and it feels divine.

She looks up and at Anthony, I can't see him. She then looks at Donna and tilts her head towards my cock. I can't see what Donna did, but I can see the huge smile on Karen's face. Oh shit, every time a woman smiles I get pain. This isn't good, I am nervous. However, it's Karen that looks nervous. She moves back and presses her ass up my cock.

After her pussy goes past my cock I assume she will keep going. She doesn't. She changes her angle and then sits down on my cock. As she does this she lets out a big moan and I feel a pussy quickly enveloping my cock. She is going too fast, she screams a little. She starts a slight motion of rocking back and forth on my cock as she attempts to massage me.

Donna gets on her knees and assists with the massage by rubbing my arms. Mom mirrors Donna on my opposite side. Karen has given up all pretenses of a massage, she is slamming up and down on my cock and it's wonderful. She is pounding me quickly, I feel my desire building rapidly. She is warm and wet, I slide effortlessly in and out of her pussy. She is on fire. Her breathing is heavy and in time with her thrusts.

She is sweating, her entire body has a gleam, a glow almost. She is grunting and seems to be struggling with something. I sense her picking up the speed. Her juices are leaking down my legs and into the carpeting. She is squeaking. This is going to be good, I am on the edge as well.

I warn, "Karen, you want to get up now, I am close to blowing my load in that sweet pussy of yours. You don't want that."

She ignored me and kept pumping, I am worried now, I don't want her getting pregnant with my child, not when she just started dating Anthony. Too late, she orgasmed. The anvil in her cunt closes on my cock, I can't cum. As her orgasm begins to subside, I shoot my load into her warm fertile womb. I feel ashamed, I cover my face. How can I look at them?

While in my own world, Karen falls on me. She is breathing in my ear, it's turning me on again. Someone is cleaning my cock with a warm wet mouth.

Karen whispers in my ear, "Anthony is sterile, we needed a donor. We both love you very much."

She is nearly crying and only I know they are tears of happiness right now.

Jane points out, "Isn't a happy ending normally a blow job?"

Karen laughs, "In the end, I think he was quite happy."

She laughs at her own joke. She was right, I did like the ending.

Anthony rolls a 4, we gather around the table, he draws a card.

Anthony reads his card, "You have worked these women hard, time to be nice now. Give a frontal body massage to your target and eat her to two orgasms."

Anthony looks very nervous. He walks behind Donna and rubs his hands up and down her body, feeling her tits along the way. He takes his fingers and pulls her shorts down by pulling from the bottom of the shorts, not by the waist like normal people.

He grabs both sides of her panties with his fists and quickly yanks the panties down leaving Donna naked in front of the group. She shudders like a wind ran through the room. Anthony assists her laying down. He straddles her waist and massages her shoulders and arms. Donna moans.

Anthony moves down and massages her massive chest for a while. It is obvious he likes that. He moves down some more and is teasing her waist and ribs, he avoids her slit. He moves down more and now he is massaging her inner thigh and then both thighs. He moves down to do her calves and then down to her feet where he spends the most time.

Donna looks to be near orgasm just from the foot massage. Anthony is moving up her body and then leans forward to lick her slit from top to bottom earning him her first orgasm. She screamed when it hit. Her arms flung around wildly. He never stopped. He went back and forth between talking into her snatch or licking from top to bottom. The result was another quick orgasm.

I hold Donna for a few moments until she can stand up.

Mom rolls a 3 but Jane is on that spot, bummer for her.

Donna goes next and rolls a 4, she got to kiss Anthony. Surprisingly it wasn't steamy, guess they didn't do much for each other.

I roll a 6, draw a card, I strip moms shorts off, mom gets 10 strikes from a crop. Being it was my mother I couldn't go too hard. However, she earned a few that were harsher due to not standing up for me. She saw the anger in my eyes and never said a thing, she understood.

Jane rolls a 4, she does lube and fingers in my ass. Since having that strap on ream my ass, this was easy. Jane had never done anything anal, so she had fun playing with me. Nothing she did hurt, and I think she enjoyed it. We both win.

John rolls a 5 and gets to use the crop 10 times on Donna. She was sore when he finished. John went a bit harder than I would have preferred but it was certainly less than I endured with the paddle.

Karen rolls a 4 and lands in the same spot as John so she drew two cards for him. He got quite the extreme pair of cards. First, the tickler. She drove him nuts, yet I think he liked it as it could have been much worse. Speaking of much worse, the second card was the old strap-on. He got it hard up the ass and screamed worse than I did. Karen fucked him like he would have fucked her. He could have complained but never did, interesting.

Anthony rolls a 6 so he got a card for Jane and Donna. Donna got the lube and fingers up the ass treatment. She enjoyed the anal treatment, it was new to her, she went with it. Jane got a hot steamy kiss.

Mom rolls a 4 and had to do a massage with John as her target. As I see mom on top of John I realize that surprisingly, she is still in decent shape. No gym or expensive beauty products to help. Just an older woman that certainly doesn't look her age. She attacked John with her hands. It had been a long time since she had been with a real man. It was very emotional for her as she rubbed her hands up and down John's lean body.

Mom didn't ask Jane, she just fucked John when she got to the end. Handjob just was not enough for her. I know John enjoyed the fucking mom gave him, but I think mom enjoyed, no, she needed it more. It had been years since a man had given her that type of pleasure. She felt like a woman again.

Donna rolls a 4 and I got anal beads again. Like before, after a strap-on, this was no big deal. Been there, done that, moving on.

I roll a 4 and land on the same space as Donna, that meant two cards for her. The cards were paddles and crops. The look on her face was pure fear. The normal tendency for the hitter is to swing hard. I know how that felt first hand and no way I can do that to Donna.

I try a different approach, I swung about half to two-thirds strength. It stung just a bit but not too much. The first swat with the paddle surprises her. She was expecting what I received. The second swat came in the same way and she let out a moan. I knew I hit that fine line between pain and pleasure.

On the tenth swat with the crop, she squirts and is begging for more. Lucky for her, ten more swings with the crop. I went easy with swings one, two, and three, they were still too hard. I continue to ratchet down the pressure and found it on the fourth when I got a moan. Five through ten were the same.

Everyone is surprised, their minds are running, why was that different?

Donna explains, "He didn't hit me hard. There was enough pain for humiliation but after a few the pain was replaced with jolts of energy that fired into my pussy. It was insane, it was awesome." I got a huge hug.

Jane rolls a 2 and put a nice feathered butt plug in John's ass. The feathers are just for looks, unlike the ones teasing Donna.

John rolls a 5, Jane earns a pair of nipple clamps. She screams as John places one on her right nipple and then a second on the left nipple. She sat thinking about the sensation, it's written on her face. John got a big kiss as a thank you. I never did get that pair back.

Karen rolls a 3 but Jane is there, she passes.

Anthony rolls a 3, Karen now has a jeweled butt plug. Anthony first took out a small plug not wanting to hurt Karen, but she shook her head no. Anthony picks out a larger plug, she shakes her head no. He pulls out another that was just way too big, Karen has both a look of horror and shock on her face. Anthony drops it back in the box and comes out with one that has jewels. Perfect, she smiles.

Karen uses both hands to pull her ass open. Anthony uses a generous amount of lube and then starts pushing the cone section into Karen's ass. He is using force but is going very slowly.