My girlfriend Wendy always said Chris was a ‘boor’. I told her I was very aware, but I had known him since grade school. To be truthful, he wasn’t my favorite friend, but we went way back and ran in the same circle. Chris was actually a bit of a bully in school. In college he joined a frat and even now, two years after graduating, it seemed he would never really grow up. A 6’3″ child-man.
Chris, on the other hand, thought Wendy was great. Most guys did. Wendy was not wild but she was fun to be with and generally easy going. She had a pretty enough face with (dyed) blonde hair, big red lips and brown eyes that squinted when she smiled. What got men’s attention though, was her body. She was not skinny, but her curves were just what drives most men wild; big hips, big ass and ripe tits that most guys saw before they even looked at her face. Wendy never really dressed slutty, but she certainly never tried to hide her curves so she got a lot of stares everywhere she went.
Chris was rude from the start when he met Wendy.
“Dude, she is way out of your league!” he said, looking at my girl but talking to me.
Wendy smiled a bit at this but then he turned to the friends with us and added “I get dibs when she’s done with him!” I could tell Wendy was pissed but everyone laughed and I just let it go. Chris had always been like that and if I made a big deal he might have laughed, got me in a headlock and made me look silly.
The general pattern continued the many times the two of them met. We were all young and there was a party at one of my friends’ places almost every weekend.
Chris picked up quickly that Wendy was friendly with a couple that we went out with from time to time and noted that she kissed both of them when we arrived at parties. He would insist that she kiss him as well. Wendy would sometimes resist but Chris was insistent so she would end up giving him a kiss on the cheek. Eventually she would do this without being asked just to shut him up. If Chris had had a couple of drinks before we saw him he might give her ass a small squeeze. The first time this happened Wendy complained to him and said to me, “I can’t believe you let him get away with that!”, but after that she would just give him a playful shove.
To be truthful, it wasn’t only that I didn’t want to make a scene. It turned me on to see guys lust after Wendy, and Chris was the most overt. I found myself getting aroused when he would palm her butt or whisper loudly that he was looking forward to his turn when she was done with me. Wendy would still call him a boor, but like me she seemed to get used to it over time and took him less seriously.
One night Chris was going a little harder than normal. It was spring and Wendy dressed in a short tight skirt with bare legs and a tight top. Chris whistled when we arrived and as she kissed his cheek he groped her butt and told Wendy she looked ‘sooo hot’. He implored her to give him a ‘spin’ and when she finally turned for him he told her she had the nicest ass in the city. Wendy took this as her cue to go get her own drink. When she came back later Chris was telling me loudly how lucky I was to have a ‘firecracker’ like Wendy and that he doubted I could keep up with her. Wendy never said anything to me but I could tell she was disappointed that I just laughed it off. She got over it and we had an energetic sex session that night with her seeming more into it than normal and me a little turned on by their sexual tension.
Summer came and while I continued my training to become an accountant, Chris took off to Canada to work on the oil rigs. When he returned in September, me and a couple of guys met up with him at a sports bar. He had clearly added muscle to his broad frame. He was tanned and somehow even seemed a little taller. Chris was still cocky, but seemed to have blended in a quieter confidence. We headed over to a friend’s party.
Wendy arrived at the party a little later, after having stopped for happy hour drinks with some office mates. I could tell when she walked in that she had had a few glasses of wine. Her cheeks were bright red and she was laughing in a silly way she did when she was buzzed. She looked great though, wearing a white blouse, a short black skirt and bare legs.
I took a step towards her, but Chris literally bumped past me to greet my girlfriend.
“There she is!” Chris smiled graciously. “It’s been a long time…I need a big kiss!”
To my surprise Wendy giggled and let out a little squeal. “Chris! You look great.” Then she smiled, “I guess I can do that.”
Chris didn’t give her a chance to change her mind. He pulled my girlfriend close and gave her a long kiss on her plump lips. The room went a little quiet as my girlfriend made out with my friend, his hand pawing her ass cheek. Then someone let out a “whoooooah!”. Wendy broke away with a smile and I felt a wave of humiliation run through me. Chris put his arm around Wendy and guided her to me and some friends. He didn’t continue to hold her, but the two of them stood close and he told us some stories from his adventure.
As the night went on I noticed they were talking a lot, with Chris’ hands finding their way to her shoulder, knee and even back on her ass at various moments. Nothing that warranted making a scene, especially since Wendy was clearly fine with it. I also noticed that Wendy had a drink in her hand at all times. Chris seemed to be making it his mission to make it so. Based on how much she was gigging and how flirty Wendy was acting it was clear to me she was buzzed. At one point she said she wanted to feel Chris’s biceps and he made her agree to give him another kiss before he ‘allowed’ her to do so. Watching him take her in his arms and kiss her again I felt myself harden fully so I made sure to stay seated.
The party was winding down and Chris came and sat beside me when Wendy went to the bathroom.
“Dude, I think your girlfriend is dtf me!” he said laughing. I looked around the room, worried one of the few remaining people might have heard him then tried to laugh it off.
“Haha…she’s not that drunk Chris.”
Chris seemed irritated that I wasn’t taking him more seriously. “I mean it dude. She slipped me some tongue when we kissed earlier and I’m pretty sure she felt I was hard.”
Just hearing him say this about my girl made me hard. What was wrong with me?
Wendy walked down the hall and was seeing one of our friends out. Chris spoke quietly, “I’ll bet you I can get her naked before the night is over.” he boasted.
I wasn’t sure what to say. It was already past one, wasn’t the night basically already over? There was now just myself, Wendy, Chris and the hosts, Naomi and Ted, still at the party.
“No way.” I said, hoping that might put an end to it.
“Yes way.” he laughed. “Let’s bet on it.”
“Bet?” I asked dumbly.
“Yeah. I made big money this summer. If I can’t get her naked I’ll pay you $500.”
This seemed crazy to me. Chris was really going to give me that much cash? I tried to think it through and realized I had had quite a lot to drink myself.
“Well…what if you win?”
Chris laughed, “You worried bro? If I win I will probably end up fucking her, so you don’t need to pay me on top of that.”
I looked over at Wendy who was in the next room talking with the couple. “I don’t think…”
“Only one rule.” Chris said as if it was settled the bet was in place, “If she asks you at any time if you are ok with what is happening, you can only answer, ‘Whatever you want babe.'”
I nodded, more processing what Chris had said, but he took it as an end to the negotiations. “Good bro. That’s key. This should be fun.” He patted me hard on the shoulder, “You can just sit and watch if you want.”
With that Chris got up, walked over to Wendy and put his hand around her waist familiarly. I stayed seated, not willing to risk anyone seeing my erection.
When I made my way over I had to stand between the two couples. Chris winked and lowered his hand over Wendy’s ass and I felt my cock stir. Wendy continued talking as though she was just fine with another man’s hand on her butt. I wondered what Naomi and Ted were thinking.
Chris talked about how great the weed was in Vancouver and when asked for details he mentioned he had some with him. Ted was enthusiastic and Wendy said she’d like to try. Wendy didn’t smoke often and I was going to caution her on having some after all the drinks, but I realized this might break my agreement with Chris. Soon we were all sitting and passing the weed around. When Wendy got up to give Chris the joint back he pulled her on to his lap. He took a big toke then I had to go to him to get my turn. Sitting alone on the floor I felt the now familiar combination of humiliation and arousal as I watched my girl giggle and wriggle on my friend’s lap. He was not discreet about his hand stroking her bare leg. Naomi and Ted seemed embarrassed for me as he would whisper something in her ear or blow smoke in her mouth.
Naomi was telling us something about her and Ted’s trip to Iceland but I was noticing Chris kissing my girlfriend’s neck. She was half pushing him away but giggling while she did so.
“Are you ok with your friend kissing me like that?” Wendy asked me, laughing.
I felt all four of them looking at me. I swallowed hard. “What…whatever you want babe.”
Chris laughed loudly and I felt a wave of shame. Naomi looked at her phone and said it was getting rather late, and we took her obvious cue. As we left Chris wasted no time in making it clear he wanted the night to continue.
“I have another joint…should we head to my place or yours?”
Wendy said she was getting tired, so we should head to our place and Chris took control in ordering us all an uber. We all got in the backseat, with Wendy in the middle. I put my hand on her leg possessively…there was no rule that prevented me from doing so, but Chris smirked and put his hand on her other leg. As we drove he stroked her leg sensually with Wendy just smiling and lying back in her seat as he talked about the wildlife he had seen over the summer.
Chris followed Wendy up the stairs as she slowly led us to our walk-up apartment and with a complete lack of subtlety commented that her ass looked better than ever. Wendy did not seem offended at all, telling him she did a lot of squats to keep it like that.
When we walked in Chris pushed further. “I’ve always wanted to see it.” he said as I rolled my eyes. “Can you give us a look?”
This was his big play?, I thought to myself. Of course she wasn’t going to just show him her ass. She laughed at Chris’ boldness but blew him off, sitting down.
“I don’t think that’s a good idea…you probably got a good enough look going up the stairs!”
Chris did not let it go. As he lit up the joint he pushed, “Come on Wendy…it’s just the three of us and I didn’t see a woman all summer.” Chris then looked at me and added, “I know Joe won’t mind.”
Wendy giggled and shook her head then looked over at me as she took a long toke.
She blew some smoke out then asked me, “Honey, would you mind if I showed Chris my ass?”
I realized I was trapped and things were heading the wrong way but I was a man of my word. I winced as if in pain and answered, “I…errr…whatever you want babe.”
Wendy’s eyes widened as she looked at me incredulously. She then looked at Chris who looked like the cat who ate the canary. She sat there for a moment, thinking as she passed the joint back to Chris then finally said, “Well…if he doesn’t mind…”
My heart sunk and my girlfriend stood up a little unsteadily. “You really are persistent.” she said to Chris. She pointed for him to sit down and Chris obeyed eagerly. She then told me to sit down across from him.
I had expected she might flash Chris, but instead I watched her fumble with her zipper, then pull it down and let her skirt drop to the floor. My girlfriend was now standing before my friend in just her black panties. Chris smiled up at her and motioned for her to turn.
‘Tell me how much you want to see.” she taunted him and Chris immediately told her how desperate he was to finally get a look at her perfect ass. As he did so I was looking at Wendy’s, indeed wondrous large ass, covered only by a tiny thong, knowing she was about to reveal it to my frenemy. Wendy turned slowly until her ass was a few feet from Chris and he moaned appreciatively. She put her hands under each cheek and jiggled her tight ass for him, something she had done for me a number of times.
“Oh Wendy, you are perfection.” he said appreciatively, then added with a sneer, “I’m sure Joey has no idea how to handle a wildcat like you.”
Wendy did not seem to take offense, instead she swayed her ass back and forth, clearly loving the attention.
Chris pushed further still. “Pull down your panties for me.” he instructed my girl, “I want to see it all.”
To my relief Wendy balked, telling him he should be very grateful she was giving him such a good show. Chris retreated a little, telling her he was “so appreciative” and kept his eyes fixed on my girlfriend’s big ass swaying in his face.
Speaking softer now he implored, “Could you…bend over for me?”
Wendy seemed to consider the request. She looked at me for the first time since disrobing but didn’t bother to ask. She took a step towards me, reached down to place a hand on each arm of my chair and bent over so her face was right in front of mine. She looked me in the eyes as she gave Chris the view he had requested, her ass raised provocatively. I was sure he could see her asshole given how high she raised her bum for him. I was rock hard and shifted in my chair as my girl stared into my eyes.
“God you are such a naughty girl Wendy.” Chris said in his deep monotone. He stood up and placed a hand on her ass cheek. Wendy did not object and in fact she smiled as she continued to look at me.
“Such a naughty girl.” he repeated, as he groped her. “What am I going to do with you?”
I thought Wendy was about to answer but Chris answered his own question with a hard slap on the same cheek. Wendy yipped with surprise and started to straighten up but Chris pushed down on her back with one hand and swatted her harder. with the other She yelped again, but this time added a moan. Chris spanked her two more times, alternating cheeks and my girlfriend stayed in position for him, her eyes locked into mine.
“I can’t believe you are letting your friend spank me!” she finally said to me, breathlessly.
Chris spanked her hard two more times. Wendy enjoyed being spanked, but I had never done so this hard. Wendy lowered her head and seemed to raise her ass even higher. Looking down in my lap she exclaimed, “Oh my god Joe…this is making you hard!’
Chris laughed and Wendy looked confused. Looking in my eyes as Chris stroked her ass cheek she stroked my cheek and said, “Oh…it’s ok babe.”
Chris spanked her a few more times then suddenly pulled her up, turned her around and kissed her hard. Wendy did not resist, in fact she pushed against him while he pawed her ass, his fingers falling into her ass crack. This was a long, passionate kiss with their tongues exploring each other while I sat and watched. He took my girlfriend’s hand in his, and directed it to stroke his hard cock through his pants. I sat there, mesmerized, perhaps even paralyzed, by how quickly this was unfolding.
SMACK! SMACK! I was brought back from my trance by the sound of Chris’ giant hands spanking my girl’s ass hard.
“Who’s my naughty girl?” he taunted as he landed another hard swat.
“I…” Wendy didn’t finish before another spank hit her and she moaned.
“Tell me!” Chris commanded. ‘
“I am!” Wendy said quickly. “I’m your naughty girl.”
Chris kissed her hard again and I watched his hand pull her thong down below her ass cheeks so the bare ass he coveted was now two feet from my face.
“Yeah you are.” he laughed. “Take this off.” he said, pulling at her blouse. Wendy started to unbutton it for him and he gave me a smug look. “Pull her panties down for me!”
This was not part of our bet, but I didn’t hesitate long before I reached over and pulled them down my girlfriend’s legs. Wendy finished unbuttoning and Chris lifted her blouse off her shoulders. Wendy now stood naked before him and he assessed her with a sly smile.
“Wendy, I have waited for this a long time. Now you will finally get what you really need.”
Wendy turned to look down at me. It was clear to all what was going to happen but she seemed to want to assure I was ok. Her look was an incredible mix of sweet concern and great arousal. I nodded and she gave me a little smile. Somehow I felt I wanted this almost as much as she did.
“Oh, you really want this don’t you?” Chris teased her. I looked down from her eyes and saw Chris had two fingers buried deep in my girlfriend’s pussy. Wendy was facing him now and moaned her confirmation.
I watched Chris put his hand on Wendy’s head and lower her to her knees. “Show me how much.” he directed.
My sweet Wendy unbuttoned his pants and pulled out his cock. It was bigger and thicker than mine but she gamely wrapped her lips around it and started sucking him as he pushed in and out of her. I looked up for a moment and saw him smirking but i could not bear to look him in the eyes. Instead I watched my naked girlfriend, on her knees, sucking another man’s cock just in front of me.
Chris pulled out, lifted her up and turned her around. He bent her over so she was once again looking in my eyes, but this time he pushed his hard cock into her from behind. Wendy moaned louder than I had heard her do in the past as he started to pound her again and again. I knew she was cumming when I felt her grip my hands tight and close her eyes. The orgasm seemed intense and when it was over she had beads of sweat on her red face.
“You are such a good slut for me Wendy.” Chris said as he pushed in and out. She was shaking from the impact every time he did so and I wondered if she had ever been fucked this hard. Finally he went quiet, then started grunting and I realized he was shooting into my girl.
When he was done with her Wendy fell into me, clearly exhausted by being used like that. I felt a wetness some from her on to my pants, but stroked her hair and kissed her forehead. Chris looked down at us while he put on his pants.
“Aw, that’s cute. You take care of her for me until next time Joey.”
He let himself out soon after and I asked Wendy if she was ok. “I am.” she said with her eyes closed and a little smile on her face. “That was pretty wild. Do you think we could…do it again one day?”
I looked down at her head on my shoulder and answered, “Whatever you want babe.”