Fenway Ch. 02 - Tracy's Box

Tracy and I had some great sex in the weeks following our encounter at Fenway. Over time, though, that sexual charge began to wear off. We had fallen back into the old routine. Now I'm not complaining, anytime I get to have sex with Tracy I feel like the luckiest guy on earth. Not only that, but I fucking love this chick. She is the best companion any man could have. Every friend of mine has told me how lucky I am. That being said, our new sexual dynamic made me a bit nervous.

"Remember when I said I wanted to do that again?" Tracy whispered after we had sex one night.

"Yes, of course I do. I've actually been waiting for that shoe to drop." A surge of adrenaline shot through me. "Listen Tracy, watching you fuck another man was, and probably still is, my top sexual fantasy. I just want to be very clear, I am not going to be a fucking cuckold." There, it was off my chest.

"Babe, what the hell is a cuckold?" she said with a slight smirk.

"Man, we need to watch more porn together. A cuckold is a guy who sits at home cowering in a corner with his cock in a cage while his wife goes out and fucks anyone she wants, with or without him present. He may even be expected to eat out her pussy after some rando has filled her full of cum. All this while being utterly submissive and constantly humiliated." I said this all in one breath so I ended with a big inhale. I looked at Tracy trying to read her face. Finally it all seemed to come together.

"Oh God, that's not you at all!! You would fucking divorce me first. I would never ask that of you, my love. But I do want to have some more fun like we did at Fenway. That was intense."

I could tell her labido was revving up. I had to take control of this situation. "Would you like to hear some of my thoughts on this subject?"

"Go for it big guy!! Get the ball rolling and we'll see where this goes." She slapped me on my ass kind of hard.

"First of all, what happened at Fenway was very spontaneous. Something like that may never happen again. That means whatever happens will need to be planned and initiated by us. I also think we need some ground rules." I stayed silent to give her a chance to respond.

Finally, after a minute of contemplation, "Yes, I could see where some guidelines would be needed. What are you thinking about?"

"Well fuck. First of all, the main reason we are doing this is for me to watch you and for you to enjoy yourself. So I would say I should ALWAYS be with you if something is happening. Do you agree?" I had a knot in my stomach when it took her a full 5 seconds to start answering.

"I would say yes because I know this is non-negotiable for you, but I think we should leave any of these 'rules' (she holds up the air quotes) as being the jumping off point. We might want to change them in the future." She looked too confident and comfortable having this discussion.

"Ok, if we change a rule then we both have to be in agreement. For now and probably always, I will want to be there when it happens." This is starting to get me tense."And! I can stop the action if something feels dicey."

"I mean coitus interuptus is a pretty lousy thing to do. I don't think a little bit of jealousy should allow you to stop things."

"I agree, but in the throws of 'coitus', (I threw up the air quotes) you may overlook something dangerous and I just want us to be safe."

"Ok, I can live with that then." It looked like just talking about this was turning her on. I think she can't wait to get fucked by someone that isn't me.

"Now to broach another subject. Since you've had and will have sex with other men, am I allowed to have other women? Not that I want or need that." My questioning eyes were staring right into Tracy's beautiful eyes. 'God she is so fucking beautiful!!'

"Babe, I don't think I can handle that. At least not yet. I'm too afraid of thinking you don't love me anymore. Even this plan scares me to my soul. I love you too much to take risks but I want to do this for both of us." She was shedding tears at this point which made my insides melt.

"Babe, I'm sorry I brought that up. It just seemed like I needed clarification. I don't need anybody but you. When you fucked those guys it just made you even more hot and sexy than you already are."

Tracy sat with remnants of tears still in her eyes. After a few minutes she began, "We don't have to do this. We could just go on the way we are now. I'm content with keeping our marriage safe. You are the most important thing in my life."

"That sounds boring. I think our marriage is strong enough to withstand a little tension but lets start slow, ok?"

"Ok" she managed a smile that grew slowly into an excited chuckle.All I could think was that I had opened Pandora's box. Or in this case, Tracy's box.

= = = =

My best freind, Aaron, graduated the same year as me from Brocton High School. We didn't plan on going to the same college but we both ended up at Boston College. I studied biology and chemistry while Aaron was a computer science major. Two years later, Tracy arrived at BC and became freinds with us.

We were immediately infatuated with her. She was the quintessential woman. Not just fucking beautiful with her perfect tits and ass, but a fantastic personality. She and I hit it off right away. I'm sure Aaron was pretty pissed that I got to her first but he probably figured he would be up next after I blew it. That never happened though. We ended up getting married the year I graduated and Aaron was my best man.

I had a great job lined up with a pharmaceutical company. Once Tracy graduated we bought a house in New Hampshire not far from where we both worked. Tracy was working in the mental health/addiction business. Unfortunately there is high demand in this field so finding a job near home was pretty easy.

Aaron has finally landed a bride. It's hard to believe it took him this long since he makes 6 figures and he is a 'babe' as Tracy says. I thought he might be playing the field but he always struck me as a family type man. His bride to be, Trisha, is very beautiful. In fact she looks a lot like Tracy (but not as perfect, lol).

"Have you gone to get measured for the tux yet?", Tracy asked.

"Trace, I'm working my ass off right now trying to be ready to be on vacation. All I have done so far is book the rooms at Encore resort for the batchelor party." I exclaimed with exasperation.

"You are an idiot! Seriously, would you like some help? I have time to do some stuff for you." Tracy has always been very energetic and helpful to me or anyone that needs help, to a fault. It's one reason I love her so much.

"Fuckin A right, I'd love some help. Can you pick up all the liquor, beer, and food?"

"Sure, how about strippers? Did you line up something yet?" She was grinning at me like I had to admit whether we were getting strippers.

"I'm not sure that's a good idea. Some of the married guys might be under strict orders. Ya know?"

"Oh come on James! This is your best friend's batchelor party! You're the best man. Don't you think he'll be disappointed if there aren't strippers. What batchelor party doesn't have strippers? I can set that up too if you want."

"Fuck it! I guess you're right. Yeah, go ahead and set it up. Thank you so much for doing this for me, I owe you." I began thinking about something that hadn't been discussed yet. "So are there going to be strippers at the batchelorette party?"

Tracy smiled coyly. "I don't know for sure but if I know Sammy, this should be one hell of a party. She might even get those dancers that let you touch their cocks, suck their cocks, or even fuck. What would you think of that?" Tracy smiled broadly again.

"I'm not going to be there. That's rule number one, the only rule so far!" My mouth said that but my brain screamed at me how awesome it would be to watch her fuck a male stripper!

"Well, I'm not going to be at your party either. How do I know YOU won't fuck a stripper?" She had her thinking face on now. "Wait, I have an idea. What if we had video at the party so you could watch what happens?"

"Fuck! I won't be there but it's almost as good. Plus I can watch what all the other girls do. Wicked pissa, I'm in!" My dick was hardening just at the thought. "I know some security camera apps that would work nicely for this. The video is saved by the app so you won't run out of space on the phone. It also records audio. Plus, it can be opened by the other person to watch in real time without showing on the screen."

"That sounds perfect, but if I'm being watched then I want to watch you with the app too."

"I am not planning to fuck a stripper, but I can understand why you would want to watch. The only thing is that you would have to swear you won't tell anyone else what you saw. It's not fair to the guys if you leak info to their wives."

"Right back at ya, big guy!"

When I had finally finished at work and started my vacation my mind began to relax and think about things like how fucking awesome it was going to be to watch and listen to the batchelorette party. I know most of those women and I would love to see them doing naughty things. But most of all I couldn't wait to see what my naughty wife had in store for my entertainment. I didn't try to have sex with Tracy in the two days before the girls party so my dick would be longing for action and she would be primed. I think she had the same plan. Hopefully, I won't jerk it all night watching the action, but my track record says that's not likely.

True to form, I awoke the day of the girls party with morning wood after some erotic dreams about my sexy wife. The girls were having their party at the home of the Maid of Honor, Sammy. Sammy is one of Trisha's best friends that we have known about six months now. She certainly is a partier and has a very wild side. It's actually surprising that she's still single since she is very attractive but I think she wants it that way.

Tracy and I had tested the security video app we had added to our phones and found it to be very effective. She headed out for Sammy's house after lunch wanting to help with setting up for the party. On her way I hit the "watch" button on my app which opened her camera and microphone. She was obviously in a party mood with the sound system blaring Sublime and singing at the top of her lungs. I couldn't see anything since her phone was in her purse so I stopped eavesdropping.

I opened an app for buying tickets to events at the last minute usually much cheaper. Today I wasn't looking for cheap, I was looking for anything I could justify to myself or Tracy as reasonably priced tickets to the ALCS game 4 at Fenway against the Astros. Most of the tickets were outrageously expensive. I did however finally break down to spend a boat load on two tickets next to left field. The game is tomorrow so I'm hoping Tracy doesn't have too big a hangover.

After having a little lunch I couldn't resist going back on the app. Sure enough Tracy had arrived at Sammy's place and already had the phone setup so I could easily see the entire living room. Tracy and Sammy were going in and out of the room placing food around and bringing in wine and liquor to the small bar area that was between the living room and kitchen. Whenever Tracy passed by the camera she would give her fine ass a wiggle for me.

They both had started drinking what looked like red wine already. I could also hear pretty well their chit chat. "So are you seeing anybody these days?" Tracy asked Sammy.

"I'm fucking a few people once in a while if that's what you mean but nobody steadily. You would think I could find a steady partner easier since I'm bi." Sammy answered.

'Wait, what?' I had no idea she was bi-sexual.

My wife responded like she already knew this fact. "Yeah, but it must be nice being single and every other single person is in play. I'm just lucky I found such a great guy. I couldn't be happier." She said the last part louder in case I was already listening. I think she knew how excited I was about this and knew I was already there watching her.

The small talk went on for a while and they seemed to finish setting up faster than they thought. With an hour and a half before guests were due to arrive and several glasses of wine in them, the conversation came around to sex again.

Tracy asked, "So when you have sex with women, are you using dildos?"

"Yes, or we can do oral, scissoring, there's really a ton of things women can do for fun," she ended with a wicked grin.

"Hmmm, sounds like fun but I don't know if I could do the oral. I can taste myself but other women? I don't know."

I could tell by the way she wiggled in her seat she was getting wet talking about it. My cock was raging and I was cheering her on at my end. "Come on, Babe!!"

When I thought it was over, Sammy pulled out a large glass dildo. She showed Tracy saying, "This is one of my favorites."

"That looks a bit large for me" Tracy giggled as she turned pink in the face. "Bigger than James, that's for sure!"

"You want to hold it? It's not as big as it looks." Tracy went over and took it out of Sammy's hands without another word. She stared at it and caressed it with a look of longing.

"YEEEESSSS!!!!" I yelled at the top of my lungs.

"Go ahead try it out, nobody will be here for a while." Sammy was all smiles.

"Are you going to watch me?"

Sammy smiled widely and said honestly, "Well, I was hoping to if you don't mind."

"Ok, then come over here and help me pull my pants off."

It was so fucking erotic seeing another hot woman taking off my wife's pants. Once her yoga pants were removed Tracy looked straight into Sammy's eyes and slowly eased here panties down to her knees and let them fall to her ankles. She lifted one leg out and then kicked the panties toward Sammy with her other foot, giggling. Sammy caught them without taking her eyes off Tracy's crotch.

Tracy leaned back onto the couch looking at the dildo again with lust in her eyes. She brought it to her slit as Sammy looked on as if in a trance. I am certain now that Sammy has a thing for my wife. Oh how lucky am I?

With her eyes glued to Sammy's eyes, Tracy moved the hunk of glass slowly up and down her already wet labia. She rubbed it back and forth over her clit a few times then ran it back down to her hole. Her breathing was becoming audible. Finally she started to push it in as Sammy bit her bottom lip still looking totally mesmerized. She took some time to get it in her, slowly sinking it in. "Oh fuck, it's big!" I could see the pink insides of her pussy through the glass as I finally remembered to pull my dick out and started to stroke it a bit to make up for lost time.

Tracy was now pushing and pulling the dildo fully into her pussy. I could now actually hear her wet pussy sloshing around the glass. In a raspy voice Tracy said, "God this is so big, would you please show me how YOU use this? I don't have much experience with these." Caught off guard, Sammy jumped up awkwardly but quickly made it to right in between my wife's legs. She took the end of the dildo and slowly worked it into my wife's pussy. I could tell Tracy was fully engrossed in the action and most likely has forgotten that I'm watching. I could almost feel the electric shock she felt after Sammy took control of the dildo.

"OOOH, that's big, don't go too fast yet." Tracy said as a dew broke on her forehead. Sammy was being patient with her working of the dildo, slowly working it out and back in several times before starting to try to get a rythym going. I thought I saw her flare her fingers over Tracy's pussy as the dildo bottomed out. I could see her fingers brush over Tracy's mound.

Sammy scared me when she totally removed the dildo from Tracy but then brought it to her mouth and sucked on it. "MMmmm", she acted like it was the most delicious pussy she ever tasted. She reinserted the dildo, started pumping again, and put her free hand at the top of Tracy's pussy. She rubbed over her clit area with her fingers slowly which made Tracy start moaning loudly.

"My turn", Sammy said as she pulled it out of my wife. Sammy sat down, pulled up her skirt and pushed her panties to the side in order to plunge the dildo deep in her own pussy. Tracy now had the same trance look that Sammy had moments ago but for the first time turned and looked at the phone she had setup to watch. Now I knew she remembered that I was watching. I hope to God that makes her more aroused. I can now hear the wet sloshing of Sammy's pussy confirming that the show Tracy had put on was driving her crazy.

I had to stop touching myself. I felt like it was going to be a long night, I might need to ration my orgasms.

With Tracy still staring intently at her pussy, Sammy got a strong rythym of her own going. She was on the edge of climaxing when she pulled out and handed it to Tracy once again. "Taste it" she said in almost a whisper. To my amazement, Tracy brought it to her lips and licked it. I'm sure the powerful sexual charge of what was happening helped her to enjoy the taste when she said, "MMmmmore please."

In one quick motion Tracy fell to her knees in front of Sammy and pulled off her wet panties. Sammy had the sense to say, "What about your husband?"

"Trust me when I say he will be good with this. I will be telling him everything and he will fuck me hard and long afterward."

With that out of the way, Tracy tentatively put her tongue on Sammy's labia as she pulled them apart with her fingers. Before long she was enthusiastically licking up and down the slit. She, most likely purposely, had avoided Sammy's clit for the first few minutes and still had Sammy moaning loudly in ecstasy. When she finally landed on her nub with her tongue, she pulled her tongue in and covered her entire clit area with her mouth. I imagined her tongue rotating hard on the tiny jewel. It took literally 30 seconds for my wife to bring her to a full blown body shaking orgasm. "Oohhhhh!! FUUUUUCK!!! SUCK IT!!! UMMFFUCK!!"

Sammy took several minutes to recover. "You are good at that!." I could tell at this point that this was no ordinary encounter for our bi-sexual friend. Perhaps the fact that it was Tracy's first time with a woman made it more erotic to her. "Get on the couch." Sammy commanded, and Tracy complied, laying on her back with her legs down.

Sammy approached and pushed both her knees back while separating them. She put the dildo back into Tracy's pussy and began pumping again slowly. Her mouth slowly lowered toward Tracy's pussy. Tracy, obviously nervous and transfixed, held her trembling legs back awaiting the first female lips to touch her pussy. Instead, Sammy kissed her shaved mound and continued up her belly while continuing to fuck her with the dildo. Sammy used her free hand to push her shirt up over Tracy's head. Tracy took the hint and took off her own bra.

Now seeing my wife's perfect breasts starting to be sucked on by a woman was very hot. My cock was begging to shoot it's load. But when Sammy planted an erotic deep kiss on my wife and Tracy responded by grabbing Sammy around the neck to pull her into a more deep kiss. Well that just set me off. I began cumming all over myself. I was in heaven and my hot wife had brought me there. My wife is so hot but with another hot woman she is doubly hot.

Sammy raised up from the most erotic kiss I have ever witnessed or been part of, and kissed her way back down. She stopped with a very purposeful kiss on my wifes left nipple. She began licking around Tracy's areola and erect nipples. She then opened her mouth and began to suck hard on, what I'm sure Sammy now agreed, are the most perfect titties around.

Proceeding to kiss down her flat, sexy belly until she came back to Tracy's mound. Tracy was beginning to get highly aroused again and started to push her sex into Sammy's face. Sammy pulled out the dildo. As an apparent pro pussy eater, Sammy gave a quick lick to the clit making Tracy gasp loudly. She continued down Tracy's slit licking between her lips. When she made it to her hole she plunged her tongue deeply as if searching for something. Tracy gasped and tensed her body while throwing her head back. I could tell she was fully enjoying her first lesbian encounter. Sammy pulled her tongue out of her hole and replaced it with two fingers. Her tongue worked it's way back up slowly toward the ultimate goal. When she finally reached the edge of the clit area, Tracy was thrashing about like a fish out of water. Sammy finally worked adeptly on her clit, sensuously licking slowly over her nub and humming loudly, "MMMMMM, that's delicious." Her fingers pistoning in and out.