Group Activities - Luke & Dana

Please note, this is a true story. However, I've changed the names, ages, occupations and places to protect the other person's privacy. I have no shame so enjoy, LOL.

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Group Activities - Luke & Dana

The stripper who was hired for something else.

On a random Thursday night at 9pm, my buddy Luke and I were at this really nice ocean front home. Sitting on the coast of the OC, the view looking outside at the Huntington Beach waters was beautiful. However, the view inside this home was more of a treat for the eyes sexually. My buddy Luke was drilling the pussy of a rich snobby stuck up socialite and smacking her ass while she was sucking my cock. I usually avoided these type of women but here's how we got in this predicament.

My buddy Luke was 6'2, a part time male stripper and he had the body to look the part. He had the Greco Roman wrestler body type. A muscular build with perfect chiseled abs and a cute face. Women near and far wanted him. At the time he was 26 and I had just turned 24 earlier this month. He had also recently gotten his 2nd DUI in a few years so he couldn't drive.

From time to time, me and another friend of ours would help him by driving him when he got hired for an event when we could. We also would be there to help chaperone/manage the event and keep him away from alcohol as he had a drinking problem. Basically help drive, collect the tips, be the DJ and most importantly be the eyewitness so someone couldn't accuse him of touching any of the women without consent. He once turned down advances from a would be bride who was so furious she got rejected, she tried to tell people he came onto her. Then later that evening her fiancé came over with a gun, it was a whole unfortunate thing.

Anyhow he only had limited availability because he was also going to grad school and had an internship. Now add in all the hours of community service he had to do and he was only available a few times a month. And on this morning his booking agent called and said he had a last second bachelorette party. Kind of odd on a Thursday as primarily his bookings were for Fridays and Saturdays. But hey maybe they were the shift work hours folks like me that didn't always have the typical Saturday & Sunday off.

Luke called me and asked me to drive and chaperone tonight as our other friend was out of town. Of course as a thank you he'd treat us to a nice dinner. Luke minus the drinking problem was a pretty good guy. At the time I wasn't living in So Cal but was there once a month. It just happened that I was landing that evening. I literally went from baggage claim to the rental car area to my other buddies' house where I was staying. Hopped in the shower and changed quickly. Then off to pick up Luke for the "event".

As we arrived, we were in for a different type of "event". His booking agent had told him this was supposed to be a surprise bachelorette party. As we walk up to the door a woman named Dana opened it wearing a very tiny all white 2 piece bikini. She was a very typical beach blonde with nice implants. As a breast man I didn't care I loved them fake or real. It turns out it was a party for 1 female.....

Yep, that's right Luke was hired by this woman as an escort. Dana was 5'7, 28, slim blonde with 32DDD chest and very tanned. At first Luke told her he didn't do escorting and he only danced. She kept insisting she wanted to fuck and he can go. She even went as far as pulling out 2 grand and dropping on the table.

She rude spouts out, "So dance and take out your dick and fuck me with it." You could tell she was hot for him but there was more to it. Something was off here. She was becoming more bratty, pouting and throwing a hissy fit. She was rich, important, blah blah blah. But then after she was completely out of options she just broke down and cried.

Dana apologized for bringing us here under false pretense. She said she had gone over to her boyfriend's house (now ex) last night and found him on all fours being rammed in the ass by her male cousin. Well it definitely sucks to be cheated on especially by another family member. And seeing him in that position also threw her for a loop. As expected she made a whole scene and eventually dumped him.

This morning she woke up and her friend gave her this idea of fucking a hot guy to get back at him. But it had to be a really hot guy and a guarantee. So her friend suggested hiring an escort but when she couldn't find one right away. An agency she called recommended Luke's booking agent then he recommended Luke. Despite Dana being told he was a stripper she figured she could throw in a few extra dollars at him and she would get what she wanted. Drama, drama, drama.

Luke mulls around for a few minutes and says, "Look I've been cheated on before and I know how much that hurts. You're in pain right now and if you really think this will make you feel better I will fuck you." Her eyes light up and she starts wiping away her tears. Then Luke sprung a "On this one condition......my buddy here just had a birthday and I forgot to get him anything. So if you want this, we are going to turn this into a threesome."

She looks over at me and said "Your nowhere as hot as your friend but can you fuck any good?" Granted she was right I'm nowhere as hot as Luke but what a bitch. I haven't even agreed to any of this.

I walk right up to her face and say, "It looks like I have to agree to this, if not he won't fuck you. So here's my condition you fucking bitch. I will agree to this if I get to fuck you in the ass, if not we walk and you can find someone else?" She looks at me with these challenging eyes for a second. Then puts out her hand and we shake.

I ask if she had showered beforehand and done anal before. Her response was "Yes and a few times. You better know what you're doing."

I nod my head yes and then she leads us upstairs. Dana has this giant bedroom with one long white and one long black couch. She had this whole Ying and Yang theme to her bedroom. Everything was either white or black but complimented each other very well. She takes us over to the white couch.

I grab the bag Luke usually brings with him of random things. I pull out a rubber glove, condoms and lube. Meanwhile, Dana was already all over Luke. She was basically ripping off his clothes. I was getting hard but hung back while they started. I wanted no part of her outside of fucking her asshole and enjoying her rack.

Women with attitudes like this didn't really do it for me. Even though she was physically hot, I generally steered away from these types. The drama and attitude was usually not worth the sex. This time though I did sympathize with her. To my knowledge I haven't been cheated on yet but I'm sure it's painful to be on the receiving end of that. And I think it struck a chord with Luke as even as hot as he is, he had a woman do him wrong like that.

"Oh my, yes." I hear Dana say as she pulled out Luke's big cock. He sported a sturdy thick 8-inch cock. It was impressive. She said her ex didn't even measure 5 inches but in her mind they were more together because of their scene and the circle she could be around. Granted it still hurt he cheated but now she better understood him. Apparently he confessed that he preferred being the one getting plowed instead of doing the plowing. And he told her their time together was more fitting in their social circle.

Dana is struggling with Luke's size in her mouth. She is obviously craving for Luke and his body. You could see the lust and determination in her eyes and actions. Her mouth was not large and his thickness really gave her problems trying to suck his cock. I'll give this brat an A for effort. She is really being a trooper, working to get as much as she could in her mouth.

Both her hands were wrapped around his thick throbbing cock. Moving up and down that shaft as she kept trying to get more of his shaft in her mouth. Her hands seem as if they are choking his cock. They are wrapped around so tight and it has become so plump. Luke's face was making these contortions to show he was enjoying it even though she couldn't really get much of that big thing into her mouth.

After a helluva effort, she resided to just licking the head and shaft. Dana was a woman hungry to get fucked. It didn't take long for her to get her wish. After hearing about her ex cheating on her and with the hunger in her eyes to get thoroughly fucked by Luke, I decide to hang back a bit longer. I was standing here watching this scene and getting ready for the right moment to jump in.

Luke pushes her over onto all fours. He tears off her bikini bottom. His big thick cock right at the entrance of her wanting and very wet front entrance. He moves the tip between her pussy lips and begins to slid it from top to bottom. Her body was trembling a little in anticipation. But Luke makes her wait and is torturing her with the tease.

"Oh my god, fuck me now. What are you waiting for fuck me." Dana yells out in frustration. But to no eval as Luke is still just sliding the tip and teasing the hell out of her. Up and down with a few circular motions. "Are you going to fuck me or not, you better get inside me, asshole.'' Dana barks out this time.

As I learned from Luke this evening never underestimate the power of a good tease and denial. However, depending on who your with you cannot keep it going for too long or else you will lose the person's interest. Unless they enjoy that about it. Then he lifts his right hand up and dropped a huge spank onto her rear. Dana yells out in a mix of pain and pleasure.

At that moment of Dana yelling, Luke finally slides into her. Now you can tell the look on her face she was surprised. He goes in slowly as she wasn't used to a guy her size. And just like with the blow job attempt earlier. There is quite a bit of a struggle at the onset. Luke's thickness made things tough on many women he had been with so he was used to going slow and working into a good fuck session.

After getting into multiple positions, using extra lube, more foreplay and Dana trying to relax they were not making much head way. She only had him partially in her. Even though she wants this, she kept tensing up. So it was time to try something else. Luke suggests since I'm not as large as he is to warm her up for him.

Now after my earlier interaction with Dana's attitude issues I am hesitant at first. But she looks at me with one word in her eyes......please. Then she actually politely asks, "Please help warm me up so your friend can fuck me?" I mean gee, you don't get that question every day. Here I was hanging back and gearing up to fuck her bratty ass for my pleasure, now I'm having to help her so she can get more pleasure.

I didn't have an ego issue or was butt hurt. The reality is Luke is larger than me but he's also a good friend that I'm not trying to compete with. I know there is always someone bigger faster smarter etc. out there. Does that mean I give up at life, no of course not. My issue is more with having a mental block with woman who have awful attitudes. However, I will say her tone seems to have changed a bit.

Dana is lying on the carpet of this beautiful home legs spread and wanting me to enter her. Oh hell, I grab and place a good size pillow from the couch under her rear. It moves her groin area at a high level and angles her pussy upward, just the way I want it. I start to enter her and my hard 6 inch cock goes in with less resistance than Luke's big thing. Dana lets out a slight moan of approval and has a naughty grin on her face.

Just then I realize I didn't put on the condom but she didn't seem to care. I begin thrusting slow at first. I start getting into a slight rhythm. And to my surprise she says to me, "Come on and fuck me, I know you want to and I know I want it." With that signal so to speak, I unleash a flurry of harder thrusts.

Dana was really getting into it. My thrusts were driving her wild. The power in my hips were on full display. I'm not fully sure what got into me but I completely became enraged and was basically anger banging her pussy. Maybe it was teaching this fucking rich lady stuck up a lesson, maybe I was hot for her body or maybe I was just really horny. Heck it could be a combination of all 3. In the moment I was only sure of one thing, she was going to get a good fucking.

Dana had been so worked up and wanting to get fucked before we even got here. Then add in all the foreplay and getting ready to take Luke's cock, she was so revved up. "Yes baby, don't stop fucking me like that. Oh yes, god yes I need this. Right there, right there, yes, yes, oh fuck." Dana was calling out. "I want you deep inside me, yes whatever your name is fuck me, deeper, deeper, yes yes."

"You like your pussy getting fucked hard don't you....you fucking slut." I say to her.

"What?" Dana weakly says.

"You hire a stripper for sex and now your about to get fucked by both of us. You know you want to act out and have us do dirty things to you. You want us to treat you like a slut, don't you!" I scream at her as I continue to ravage her pussy.

"Yes, yes, Aaaahhhh I'm a slut, I'm a slut. Fuck me like the slutty woman I am." she admits. I don't think that was an admission for me as much is it was for her fully realizing the situation she's in.

"Take off your top and grabbed your breasts......that's a good little slut. Pinch your nipples. Harder, harder pinch those nipples." I say commandingly. She does everything I say. Her breathing and moaning has picked up. With her groin and hips arched up like that every deep thrust I was slamming into her with was hitting that spot just right. Add in some extra stimuli from the strong nipple pinching and we have a recipe for.......

"Oooooohhhhh fuck, I can't control myself, I'm cumming, Ooooooo." Dana screams out ecstasy. Her body is shaking but I'm still a pounding away.

Then Luke who had just been watching eagerly taps me and whispers to me, "This might be the right time for me to try again, I want to get the fuck out of here asap." Luke who was poor most of his life and his parents worked servant type jobs to the wealthy hated people like Dana. People who throw their money around to get whatever they want with no regard for others. And despite sympathizing with her being cheated on he was keen doing his job then bouncing out asap. Although in hindsight it didn't fully go as planned.

As I pull out and Dana is lying there she actually thanked me in a sincere way. Her body is now way more relaxed after her climax. I pull out and step back. Luke moves Dana back to all fours. He places his big thick cock right back at her front entrance. This time he didn't go in slow. He went in more forcefully. Dana was able to get more of him inside her this time but was still struggling.

I'm not sure why I did it but I move right in front of her and I hold her hand. Not in a boyfriend girlfriend type of way but in a helping way so she could squeeze my hand when it hurt. As Luke continues to go deeper in her I can see her face contort expressions of pain and pleasure. Our fingers are interlocked now and Luke has found a bit of rhythm himself. Moving faster, more forcefully in and out of her.

Dana's eyes were now looking deep into mine as Luke was going deep into her. I began just watching Luke do his thing for a bit as he pounds the hell out of this little brat's pussy. He wasn't totally being a jerk as I could see he wasn't using his full shaft into her. But still he was doing a helluva job punishing that pussy. Dana began moaning just raw animalistic noises vs the more coherent words she was using when I was in her.

Luke's big thick cock was doing a number on Dana's pussy. She was going to be sore after this. Her hands were shaking in mine. Luke was now using big, controlled thrust and devastating her wet pussy. In and out, in and out with intense force. I was impressed at his power and control but I guess I shouldn't have been surprised. It was really quite the sight. Luke could have made it big in porn.

Dana on all fours and just trembling. I can tell another big climax was coming. I swear Dana is being fucked stupid as she still couldn't form words. Even her moans were erratic and all over the place. Luke wasn't just doing a number on that pussy but he was also fucking her incoherent.

It was a real turn on watching this. But my very hard cock was also wanting some attention and his own climax. As Luke's cock was changing Dana's life with the great fucking he was giving her, I decide it's time for me to get off. I move my cock right to Dana's face. I don't push into her mouth; I wait for her to willingly take it.

On my knees with my cock in front of her face. Dana opens and moves her mouth over my wanting cock. Her warm mouth now has her lips around my shaft. Her head moves forward a little and begins to try and suck my cock. Obviously it was not easy for her getting fucked like this but she was trying. So here we were with my buddy Luke was drilling her pussy and now he starts smacking her ass while she's sucking my cock.

Suddenly, after a few moments in rhythm Dana pulls off and I can tell why. She lets out a huge scream as she is climaxing from Luke's pounding of her pussy. Her body falls over. Dana is thoroughly satisfied. I'm pretty sure this is not how she envisioned the night going but she got it this way.

Luke stands mightily above her. His big hand wraps around his impressive shaft. He begins to jerk his sperm all over her body. He dumps his sperm all over Dana without a care for her in the world. Like she was some worthless corpse laying there. He may not have fully hate fucked her but the way he came all over her and walked off, ouch.

Dana was laying on the floor, still recovering from the orgasm and fucking we both gave her. Luke grabs his clothes and walks downstairs. I hope Dana didn't notice his disdain for her, I didn't want any drama. I grab a couple of water bottles from her mini fridge and give her one. As we both hydrate a little she says to me, "You make me feel so slutty, are you going to fuck my ass now? A deal is a deal."

Her words caught me by surprise because I had figured she was too worn out. And in a sense I was right, her pussy couldn't take anymore tonight. I help her up onto the couch but before we get down to some fun anal penetration I was going to enjoy her rack for a bit. My hands and mouth were tasting and mauling her breasts. Her nipples looked like an eye ball and overall her surgeon did a nice job.

After I got in a good 5 minutes of enjoying her rack, it was time to fuck! I put on a rubber glove and lube up some fingers. I bend her over and begin to insert a finger. Then a 2nd and a 3rd to loosen her up back there. I slip on a condom then put a generous amount on my cock and her hole. To my surprise she decides to climb on top of me and work herself onto my cock.

Sitting on this very expensive white leather couch she was riding my well lubed condom covered cock in her ass. My back was lying flat against the couch. She was bouncing above me. Then in a surprising me move Dana pulls me up to her face. She leans forward and starts to kiss me very lovingly. I return the kiss. We would stay like this for a while, with our lips connected in a sensual way.

The position we were in I believe is called "The Wrap Around Position". Luckily, she was more leg tall then torso tall. So that our faces were close enough to kiss at this position without being uncomfortable for a long period of time. Her long legs wrapped behind me. My hands were caressing her back.

I could feel tears start running down her face. Just not long ago it seemed like she was looking to fuck for revenge. But with the way she was kissing me and her hands sensually wrapped around me, this was not revenge. She just had to have someone desire her again. She needed to feel special. At the moment, Dana just really needed to feel loved.