Lost bet leads man to the unthinkable

I'm a happily married man that happens to have a very attractive woman as his best friend. And I'm not talking about my wife; I'm talking about a true friend. Tammy and I met almost fifteen years ago when she started working for me. We both worked for the same company and it was a case of me needing an admin and her business unit being shut down so I was "given" her without the benefit of meeting and interviewing her first.

The first time I set eyes on her I knew I would have hired her regardless of her skill set. Call me a sexist if you want but she was too hot to pass up. The surprise to me as I found out was Tammy was one of the most competent and driven employees regardless of position I've ever had the pleasure to manage.

Our friendship was slow in forming. She was single and I was married so our relationship was limited to work. Then Tammy met my wife and they became friends which opened things up for me. Tammy and I had a lot of common interests like working out at the gym and hiking. My wife didn't mind me doing these things with Tammy because then she didn't have to.

After a couple of years Tammy and I were best friends. There was plenty of good natured flirting with lewd and suggestive comments but it never went beyond that.

Tammy knew she was hot and I lusted after her and she used to accuse me of wanting to fuck her which I always admitted to hoping she'd take it to the next step but she never did. What she did do was sexually tease me constantly. She'd talk about having to masturbate because she was so horny when she didn't have a boyfriend. Then use me as a sounding board when she did have a boyfriend.

For instance, she'd go shopping at Victoria's Secret at lunch then come into my office the same afternoon. After she'd close my office door, she'd face me and lift her top to show me her new bra and ask for my opinion. Then she'd unzip her pants and pull them down just enough that I could see thong and ask if I thought her boyfriend might like them. If she happened to be wearing a short skirt (which happened more often than not) she'd raise the bottom slowly till it was above the tops of her thigh highs or stockings attached to her garterbelt and ask if I thought it would turn a man on.

Yes, Tammy was a cock tease. But as far as I could tell she was only teasing my cock. She never flirted or talked suggestively with the other men in the office although she had every opportunity. All the men thought she was hot and would pay daily visits to talk with her. I'm guessing she just felt safe with me since I was married and had never tried to put a move on her.

I didn't mind her cock teasing one bit, in fact I loved it. She kept me thinking about sex every day - which was and still is my favorite thing to think about. My wife benefited from my constant state of arousal and when my wife wasn't in the mood, Tammy was my masturbation fantasy.

Jumping forward, Tammy got married five years ago and her husband and I are now friends. We're not close friends but we do golf a few times a year as well as socialize during our get-togethers with our spouses every month. I don't know if he knows anything about Tammy teasing my cock in the past and I'm not about to bring it up.

Tammy's husband trusts her just like my wife trusts me and this summer Tammy and I went backpacking together by ourselves. I'd love to tell you how Tammy and I finally had pretty hot sex on our trip but it didn't happen. We shared a tent and I saw her in her sexy bra and panties and she saw me in my boxers but it went no further.

Tammy has now managed to tease my cock for almost fifteen years and I desperately want to fuck her brains out!

This past week we were talking on the phone about football. She's a diehard Cardinals fan and I'm the same way about the 49ers. Both teams suck this year but it didn't preclude Tammy and I from doing some trash talking about their upcoming game.

I finally threw out the bet "Loser goes down!" and to my ultimate surprise Tammy said "It's a bet."

If I wasn't already sitting down I probably would have fallen over. I couldn't believe she accepted the bet! Either way I was coming out a winner. She was either going to wrap those sensuous lips around my hard cock and suck me off or I was going to lick her pussy till she came numerous times. My cock immediately got hard.

I have never rooted against the 49ers in my life but I did that Sunday. I wanted them to lose so I could go down on Tammy. My thought was that I was going to get her so worked up by eating her pussy that she'd beg me to fuck her. My cock was as hard as a rock just thinking about it.

The game was close with numerous lead changes and eventually came down to a Hail Mary pass from the 49ers. If they completed it I was going to get a blowjob, and if not, I was going to enjoy eating Tammy's pussy and hopefully a lot more.

When the Hail Mary pass fell incomplete in the end zone, I screamed "Yes!" My wife looked at me like I was nuts and asked if I had too much to drink since I just cheered on the wrong team.

I couldn't explain my thought process to my wife so I claimed temporary insanity. She gave me a very strange look as she picked up the beer bottles and munchie containers and took them to the kitchen. I just sat on the couch with my eyes closed fantasizing about Tammy's pussy.

As much as I wanted to call Tammy right then to tell her my tongue was ready to pay off the bet, I decided to wait till Monday when my wife and Tammy's husband weren't around so Tammy and I could talk openly. Obviously our spouses didn't know anything about our bet.

On Monday I didn't have the opportunity to call Tammy because she called me first.

She started off laughing and saying "Your team sucks so I don't have to! But you are going down and I'm going to enjoy this. I'm sure you're thinking you can lick me into submission and I'll let you fuck me. It might happen, but I doubt it unless you're the best pussy licker I've ever had."

I was stunned. I thought she was going to renege on the bet but she just threw down the gauntlet. I know I enjoy eating pussy more than any man alive and now I was confident I was going to get to fuck Tammy.

"Be at my house Thursday at 2:00 ready to pay off your bet." continued Tammy.

On Thursday I arrived at Tammy's house precisely at 2:00. I rang her doorbell knowing it was going to be on of the luckiest days of my life and Tammy didn't disappoint me. She was only wearing a sheer bra and g-string. I'd seen her in bras before after her Victoria's Secrets shopping trips but they were all padded bras. Tammy is a solid B-cup and liked the padding to make her look bigger. But now I was seeing her nipples for the first time through the sheer material and they were perfect.

I looked down to her crotch and could tell she hadn't been lying all these years when she teased my by telling me she shaved. No pubes were visible through the sheer g-string.

Tammy invited me into her house then turned around and told me to follow her into the master bedroom. What an ass! I'd never seen her ass naked before but always fantasized what it would look like. Let me tell you, it was far better than my fantasies. Needless to say my cock was hard as I followed her to the master bedroom.

When we got to her bedroom she told me to strip naked. I quickly took off all my clothes and Tammy looked me up and down just like I was doing to her. But with Tammy I couldn't tell if she was horny but there was no mistaking my rock hard 8 inch cock with pre-cum dripping for anything other than me being hornier than hell.

Tammy smiled and said "Very impressive! I'm not sure if I trust myself not to let you fuck me but I sure as hell don't trust you not to try with that hard-on."

"So if it's OK with you, I'm going to restrain you before I strip naked and you go down. If not, then you can get dressed and leave always wondering what could have happened. What do you say stud?"

After being best friends for 15 years I trusted Tammy with my life and wasn't concerned. I have to admit I'm into bondage so this added to my excitement. Tammy knew this about me because we'd been to an adult bookstore together a few years back where we both bought bondage gear.

I said "You'd have to drag me out of here kicking and screaming so restrain me all you want and let's play."

Tammy said "Somehow I thought you'd say that. Turn around and put your hands behind your back."

I did as told and Tammy handcuffed my hands together. Even though I couldn't get free without Tammy undoing the handcuffs, she added to my bondage by taking a rope and tying my elbows together as tight as she could. This was uncomfortable but not too painful. Next she put a blindfold on me ensuring I wouldn't get to see her pussy when I ate it. When I opened my mouth to start protesting she was ready and put a penis gag in my mouth and buckled it tight behind my head.

Now I was getting a little concerned. How was I going to eat her?

Tammy turned me back around so I facing her and she started playing with my nipples. I may be a man but I love having my nipples played with and this was turning me on. After a few minutes of pulling and twisting on my nipples she stopped playing and attached nipple clamps.

They hurt like hell and I tried to tell her so but only muffled sounds came out with the penis gag in my mouth.

Next Tammy got down on her knees -- I couldn't see her with the blindfold on but when she took my hard-on in her mouth I knew she was on her knees. She licked and sucked my cock for probably only two minutes before she stopped. In my excited state I would have cum if she continued and I'm sure that's why she didn't.

Tammy grabbed my balls and pulled hard stretching them before she snapped a parachute ball stretcher around them. I knew what it was only because Tammy told me. She explained that it was one of the special parachute ball stretchers that had hundreds of sharp metal points on the inside and if it was pulled they would cause me great pain.

I believed her but Tammy had to prove it to me anyway. She grabbed hold of the three chains hanging down from the bottom of the stretcher and pulled very hard. Without the gag in my mouth I'm sure the neighbors would have heard me scream.

"OK my little boy toy" Tammy said "Do everything I tell you to this afternoon and you'll be rewarded. If you don't, then you can expect more pain. If you agree, shake your head yes."

As well as Tammy had me tied up and being naked I didn't see where I had much choice. I shook my head yes.

"Then prove it. I want you to turn around, spread your legs as far as you can, then bend over from the waist till your head is resting on the bed."

As embarrassing as the position was going to be I didn't see a lot of options so I did as Tammy ordered.

Next thing I knew she was rubbing some lubricant on my asshole then started to work a very large butt plug up my ass. I tried to escape but in my position I was limited in my movement. Tammy took the butt plug away but whipped my ass very hard with a riding crop. I screamed into the gag and bed and only a muffled sound came out.

"Now be a good boy and let me work this butt plug up your ass or I'm just going to continue whipping your ass. What's it going to be?"

None of this was part of the bet! I was supposed to be enjoying my afternoon going down on Tammy with the hope she'd reciprocate. Now I was getting very concerned. I spread my legs even further and wiggled my ass hoping she'd take the hint and work the butt plug up my ass versus whipping me again.

Tammy did and when she was done my ass had never felt so stretched and full.

Tammy said "Here's the deal. My husband has wanted a threesome for years and I lost a bet to him a few weeks back and now must provide it. I agreed to do it but only my terms. My terms were I was going to tie him to a chair in the guest bedroom then have one of my hot girlfriends give him a blowjob then make love to me while he watches."

"But there is no way I'm going let another woman give him a blowjob much less let her have sex with me. I know two women getting it on are every man's fantasy but I think it's disgusting. On the other hand, the thought of watching a man give another man a blowjob turns me on."

"So when you proposed our bet I had the perfect solution. You lose the bet and give my husband a blowjob then go down on me. Everyone wins!"

I sure as hell didn't see it that way!

Tammy continued "What my husband doesn't know is I won't be taking the blindfold off him after I tied him to the chair. This way he won't know it's you and not one my girlfriends giving him the blowjob. And when you go down on me he'll hear the sounds of me cumming and again think it's one of my girlfriends getting me off. What do you say?"

I vehemently shook my head NO! I'm not gay and have never considered giving another man a blow job.

I felt the sting of the whip five times in a row then Tammy said "We can do this the easy way or the hard way but either way you will sucking off my husband this afternoon. You can agree to do it now or else I'll pull on your balls and continue whipping your ass till you beg me to allow you to. What's it going to be?"

I just couldn't agree to give a blow job without a fight so I shook my head no. Tammy laughed and said "Fine have it your way but you will regret this."

In my bent over position with my legs spread it was easy for her to pull my balls back between my legs and make the sharp points from the ball stretcher dig in. It hurt like hell but not as much as when she whipped my balls.

I wanted to die but didn't. She whipped my ass a few times then another hard whip on my balls. I was in so much pain I wanted to beg her to stop and allow me to suck off her husband. But no words would come out with the penis gag in my mouth.

She laughed while continuing to whip both my ass and balls telling me she'd stop as soon as I begged her to let me give her husband a blowjob. I couldn't so she continued the assault on my balls and ass.

After what seemed like an hour but I'm sure was closer to fifteen minutes Tammy stopped. She said "Oh I'm sorry I forgot you were gagged and couldn't beg me to stop."

Yeah bullshit! Thank God I was gagged and no sound came out or I knew I'd be whipped some more.

"Do you want me to continue whipping you or are you ready to beg to suck off my husband?"

How was I to answer a trick question like that? I shook my yes and Tammy chose to believe I wanted her to continue whipping me so she did. When she finally stopped again there were tears streaming down my face.

"So are you ready to give my husband a blowjob?" I vehemently shook my head yes. "Good, I hope you learned your lesson and never ever say no to me again. Because if you ever do, I will give you a punishment that will make today seem like a walk in the park."

What was Tammy talking about? This was a side of her I'd never seen before and didn't want to again.

Tammy helped me up then told me not to say one word or else as she removed the penis gag.

She said "I'm going to spray a little women's perfume on you then put bright red lipstick on you. The perfume will convince my husband you're a woman and I know he'll get off seeing some red lipstick on his cock and balls when I take the blindfold off him."

This did not add to the afternoon.

Tammy eventually led me into the guest room and forced me to kneel. With the blindfold still on I couldn't see anything so she guided my head to her husband's cock and balls. I knew what was required of me so I opened wide and took the head of her husband's cock in my mouth.

He was only semi-erect but it was disgusting and I almost gagged! Then I remembered what Tammy told me just before leading into the guestroom. "You're going to convince my husband you're an experienced cock sucker and that you love sucking him off. I want you to give him the second best blowjob he's ever had -- as in second only to mine."

"If you don't do a convincing job and he doesn't like it then I'm going to tie you face down bent over a chair and then lead my still blindfolded husband over to your ass and have him fuck your ass. Of course he will be thinking you're one of my girlfriends and will thoroughly enjoy it."

"So are you going to give him an expert blowjob and swallow every drop of his cum or do you want him to fuck your ass and deposit his load deep inside you?"

It wasn't that difficult of a choice. If I sucked her husband off I still got to go down on Tammy. If I didn't, then he'd fuck my ass and I wouldn't get to see and taste her pussy. I told her I'd give him one hell of a blowjob.

His cock immediately started growing in my mouth. I backed off so just the head was in my mouth then ran my tongue over it. Big mistake! I received a lot of pre-cum in my mouth. I knew I had to be convincing so I gave a feminine moan then went back down taking as much of him in my mouth as I could. When the tip of his cock reached the back of my throat I almost gagged again so I quickly pulled off his cock but sucking the entire time.

Now I went to work on his balls. Thank God they were shaved because I don't think I could have taken a hairy ball in my mouth and sucked on it. He must have liked what I was doing because he let out a moan of pleasure. I must have spent the next five minutes licking and sucking on his balls and even edging my tongue towards his asshole but not getting too close.

He eventually said "You're driving me nuts! Please suck on my cock!"

I obliged but this time he was fully erect and quite impressive. No wonder Tammy didn't want any of her girlfriends being part of this threesome and finding out how big his cock was. I knew just how big he was because I was trying to deep throat him but couldn't. That didn't mean I didn't give it my best shot.

I settled for trying to give him the best blowjob I could but with no previous experience my asshole was worried. I varied my pace and method. I'd start out slow and go up and down on him then work up to a fast pace. When I felt him tensing like he wanted to cum I'd slow back down then eventually let him out of my mouth and just licked him like a lollipop. I'd start at his balls then lick to the tip of his cock and give it a little suck before starting over.

I'd had a girlfriend do this to me so I knew the torture I was putting him through and was enjoying it with a sadistic pleasure. That's when I felt the vibrator start up in my ass. I had no idea Tammy had put a remote controlled vibrating butt plug up my ass but I did now.

I quickly swallowed as much of his cock in my mouth as I could in order to mute my moans. I sure as heck didn't want Tammy's husband figuring out I was a man by him hearing me. This seemed to do the trick because with my mind on the butt plug I forgot all about my gag reflex and deep throated his cock.

Now it was her husband's turn to moan. I quickly got into as rhythm of only coming off his cock a few inches then swallowing the entire length of him. It didn't take long for him to start screaming "Oh fuck, I'm going to cum!" over and over.

Then he made good on his claim and started pumping his cum down my throat. Not swallowing his cum wasn't an option as he was sending squirt after squirt directly down my throat. When his cock stopped cumming I slowly pulled off licking and sucking him clean.

He eventually caught his breathe and could talk "Tam, I don't know who that was but she gave me one of the best, if not the best, blowjobs I've ever had."

I was proud. Pretty high praise for the first and last blowjob I'd ever give.

Tammy said "Well you just sit there and recover while your secret lover now satisfies me. And no, I will not remove you blindfold so don't even ask. Our threesome partner will remain a mystery to you."
17821 days ago, 54713 reads
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