5-Year Plan

We became friends. The odd thing was because I wasn't trying to show any physical attraction (Thanks again to my cage) she would try to flirt heavier and heavier, to the point of determined seduction. Andria wasn't use to guys not falling for her.

I did see her school play. She was outstanding. Very talented. I told her afterwards how great she was. She kissed me on the lips and said, "Goodbye, Harry. I'm off to New York after Saturday's last performance. We can still keep in touch by texting and other forms of social media."

"Good luck Andria. Break a leg."

I graduated two months later and low and behold I got an accounting job for a large conglomerated in New York.

Then my last Saturday morning with Wicked Wendy arrived. After she gave me my key, she gave me my last reward. Her best offering. No, it wasn't anal or anything weird. She gave me a kiss for the first time. "Goodbye Harry. As weird as you are, I am going to miss you."

"I will miss you too. As a going away present, let me do your taxes."

"That's sweet but I don't make enough to worry about."

"Are you kidding. I see that you make well over 100K a year."

"I don't declare the hooker money."

"You should. Declare 50% of your 'extra' earnings to keep Uncle Sam happy. With the clientele you have, I wouldn't be surprised if there was a tax auditor amongst them. Don't forget, that is how they caught Al Capone."

A semi-unexpected event happened when Tony got married that summer. When texting it turned out Andria was also going to the wedding. She was a friend of the bride. I hadn't found an apartment in NYC yet. I was floored by the rent. Andria was thrilled I was coming to New York. She was looking forward to having a friend there. Speaking of which her roommate had vacated and she emphasized that I should come stay with her. I eventually took her up on the offer. The price was affordable. And the 'view' was outstanding. As it turned out we were great roommates. Our schedules never aligned, with my early to bed and early to rise versus her night owl tendencies. When she wasn't auditioning and getting the odd part, she was augmenting her income by waitressing. She got HUGE tips. We were two ships passing in the night and mine had a 'cock cage' anchor.

An unpredicted wedding invitation came a month later. Kate was getting married in our home town. It was a large wedding. My parents were good friends with Kate's parents and were attending. Because Kate was a wonderfully open person, I was given a plus 1. I fretted about attending and told my parents I wasn't coming. Work was my excuse. My parents coaxed me into coming. Then there was the plus 1. I asked Andria if she would come with me. Because I wanted to impress/dazzle Kate, I asked Andria to be my 'pretend' date.

"I would love to. Being your 'pretend' girlfriend is the best part I have been offered lately."

"Could you go the whole 9 yards and look even more amazing than you already do?" She did and she had the look I wanted. She was going to upstage the bride.

The wedding was wonderful. Kate looked smashing and happy. We sat at the back with my parents. Mom asked, "Are you staying for the reception?"

"We have a long drive to get back so no."

"You can stay at our house and go back in the morning." Before I could answer, Andria said that was a great idea.

'Great. Reception.' I sarcastically thought. I didn't want to carry on with the 'pretend' girlfriend charade. Kate and I sat at my parent's table. Mom wanted to get to know my 'girlfriend'. But the best part was that I was with the most beautiful woman there, and quite possibly the entire county. After the bride and groom danced, I danced mostly with Andria and a few with my mom.

While Andria and I were sitting out a dance., I heard from behind me. "9 at 4 o'clock." Of course, it was Kate. Andria laughed the hardest. "Oh, I see Harry showed you, our game. Hi, it is nice to meet you."

"I'm sorry. Kate, this is my girlfriend, Andria."

"Well Andria I am so glad you came. Can I borrow Harry for a dance?" Kate and I talked while dancing. "She's lovely. I am so glad for you." We chit chatted and at the end of the dance I said, 'I am so happy for you. You look positively radiant." A wedding photographer took a photo with Kate and Andria on either side of me. As a 'pretend' boyfriend I had been extremely attentive to Andria. Andria told me I was excellent boyfriend material.

We came back to my boyhood home. We were to sleep in my old room. Mom and Dad are quite progressive. "Don't do anything we wouldn't do," with a wink.

"I will shower first. I'll be quick," I volunteered. Afterwards, I returned wearing a full-length bath robe, hopping in the extra cot my dad brought up. My old bed was just a single and I let Andria sleep there. Andria came back and took off her robe. She was naked. "I hope you don't mind. I always sleep in the nude." She was perfect even down to dimples on her butt cheeks. I gulped and turned off the light.

Shortly Andria said, "Harry I'm horny."

"Sorry, Andria but we are just a pretend couple."

"But your parents are expecting us to do it. I'm so Horny Harry. You have to be a good 'pretend' boyfriend and help me out."

I relented, rose and bent over her immaculate naked form. I kissed her for 7 Mississippi's, then slowly lowered catching her left nipple then her right with the wettest sloppy kiss I could muster. Lowering further, I came to the land of cream and honey. I breathed in her earthy yet pleasant essence emanating from within. Even her pussy was a 10. Her labia were radiating a red hew and it appeared to be pulsing from just inside. My heart beat was pulsing faster as I lowered for the first touch with my lips. Sticking out my tongue, I glided in a circular, counter-clockwise motion. Her moans increased.

Then I zeroed in on her clit. Just as I like big breasts, I like big clitorises. Perhaps an inch long and just starting to protrude from the hood. Gently at first, I licked and kissed, then applied more pressure. I listened for her reaction and it sounded like her engine was revving up for the big climax. I then backed away and returned to her vagina with deep tongue penetration. She seemed perplexed, I added a digit in behind my tongue, then a second. Soon I was fingering fucking her with increasing speed, moving my tongue back to her clit. The dam soon broke and her voice rang with that pure orgasmic melody.

"Oh, fuck, I'm so close. Don't stop."

"OH Fuck. Oh F-F-Fuck.""

"Yes, I'm, I'm cumming. Fuck I'm CUMMMMING!!"

A few minutes later, I gave her another loud oral orgasm. I had used my sex 101 knowledge to the prettiest girl I would ever see.

"Why do you still have your PJ's on. I need you to fuck me." She reached over to my crotch then stopped "What the fuck is that! Take off your PJ's. What is that?"

"A cock cage. Sorry Andria, let me help you with another oral O."

"The mood is gone. Go to sleep."

On the drive home, Andria asked "You've got to tell me what's going on with you and that cock cage?" I explained how it tied in with my 5-year plan,

"Why don't you take it off?"

"I can't. Have you seen my night table? There's a table cloth over it. But it's actually a safe with a time lock set for Saturday mornings, 5:00 am. That's where the key is." (I didn't dare go down the Wendy black hole)

"I thought I was dedicated to my acting plan. Yours is obsessive."

"I'm probably crazy."

"Do you plan wearing that for the rest of your life?"

"No. just another year and a half till I get my career on track"

"What then? Do you have another 5-year plan?"

"I'm actually thinking of a 50-year plan"

"You're kidding?"

"Not really. I was thinking of finding a great wife, 2.2 children and the white picket fence". Andria smiles at this.

Chapter 4, Year 4 of the Second 5-Year Plan

I had given Kate a nice wedding gift and Kate's thank you gift arrived. It was an 8 by 10 framed photo of Kate, myself and Andria taken from the wedding reception. This factors in with my current 5-year plan.

Everybody's plans came crashing down with the Coruna Virus. Andria's acting plans are put on hold. Even her waitressing hours were greatly reduced. I told her not to worry. I would cover the rent. My accounting job was hardly affected. When I started working from home it became easier. I now spent more time around Andria. I helped her like an acting sound board and playing other parts that she was practicing.

That photo came into play with a zoom call from my job. There were normally 20 or more in the zoom meeting. Being the newest recruit, I usually had little to add. In the first few minutes of the call, my boss called me out directly, "Mr. Boyles I can't help being drawn in by that photo over your shoulder." I turned having forgotten the photo. "Is that your wife?"

"No sir. A friend"

"Who is the other lady."

Now one of my deficiencies is lack of astute, quick thinking (Many of you are even adding my poor writing, I'm sure). Because Andria was my 'pretend' girlfriend at the time the photo was taken, I said, 'Girlfriend.' "My you are a lucky man. You definitely show promise." The zoom meeting then continued normally. Later in the day I received an email from my boss inviting Andria and myself to a small get together at his house this coming weekend. What do I do? I found Andria and told her how I had absentmindedly told my boss you were my girlfriend and we have been invited to his house. "What should I do?"

"Tell him we would be delighted."

"You're okay with this?"

"Actually, I would love to."

We went and my boss Bob introduced us to his trophy wife Glenna. (Now this is where you may think this is where my boss leads my girlfriend away and cucks me like most of the stories on Literotica). However, my story changed quickly as Bob was leading Andria on a house tour. She glanced back and when she saw Glenna put her arm on my shoulder, Andria pulled away from Bob and said "I'm sorry, I'm not feeling well." Marching over to me and pulling me away from my boss's wife, "Let's go, Harry."

I offered my apologies as best as possible. In the car I asked, "What was that about? Were you worried about my boss's intentions?"

Turning to me she said, "I've handled all kinds of degenerates in my life. I could easily handle the likes of him." Pausing, Andria continued, "I am jealous. I have feelings for you. Strong feelings. I was even jealous of you dancing with Kate. When that boss's bitch put her hand on you, I lost it. I hope it doesn't spoil things with your boss."

"I have feelings for you to. If I wasn't wearing this cage, I would show you. As for my boss, who cares. Can I tell you something?...... There are a lot of accounting jobs out there."

A few months later Andria asked me if I could be her 'pretend' boyfriend at a party with her theater friends. We went and I was being attentive again. I stayed by her side but when I went to get drinks, an older guy who I would learn was a director honed in. Andria looked on to me for help. He was getting a little touchy feely.

I approached with her drink. "Oh, thank you darling. Harry this is William. He's a director in the upcoming play." She looked at me and mouthed, 'help me'. Now as I mentioned I'm tall and could be intimidating, but I had a better weapon. I reached out shook his hand excessively. "I am an accountant (and proceeded with accounting speak)" Miraculously, William said, "there's John and Margaret. Nice meeting you." And, he was gone.

"My hero" she kissed me.

"Just part of my super powers."

After 10 minutes we mingled. Most of the crowd were beautiful actors and older behind the scenes people. I meandered over to a tall, lanky woman who I recognized from the odd play Andria had been in. I saw all of Andria's productions. "Hello, I'm Harry. With Andria. You are Felicity? I remember you from Andria's last play." Before me was a true character actor. Eyebrows uneven. She was a 5 at best. But she was memorable.

She said, "The difficulty of a being a character actor. Never the leading lady, but lots of work." We chit chatted. "Nice job with William by the way, but Dustin now has his eyes set on your girl." I looked over and there was a 10 coming on strong. They looked like a great, beautiful couple. Oddly Andria didn't seem to need my help. I strolled over with a drink. Andria basically dismissed me. I went back to talk to Felicity.

"I guess she wasn't thirsty."

"Oh, she's thirsty all right. And Dustin is a tall drink of a water." We talked on further and Felicity nodded over. Dustin had leaned in and kissed Andria.

"They are probably just acting out a scene"

"Maybe an X-rated scene. Doesn't it bother you that your girlfriend's kissing him?"

This is where my poor, quick thinking shuttered me again. I came up with, "We have an open relationship." Why did I say that?

"So, you both fool around?"

"Oh yeah."

"You have some dip on your cheek," she raised her hand to my cheek then quickly pulled me in for a kiss. I backed away awkwardly. "I didn't think it was a truly two-sided relationship."

"You just caught me off guard." I pulled her in for a deep kiss, lasting 6 Mississippi's. Suddenly there was a firm tap on my shoulder.

Andria pulled me away, "Harry time to go". As I pulled away with apologies, Felicity added, "Sure. Open."

"What was that about? I told you I am extremely jealous," she fumed. I tried to explain how it happened. She was having none of it.

Then I got angry. "I am sorry Andria; I was caught in the moment. I don't have a fucking script to follow." We fought further which was very unusual. Finally, I shouted, "This is getting too complicated. I think we should 'pretend' break-up."

"No one breaks up with me." Which was probably a true statement. But we did break up.

Year 5: The last day of my second 5-Year plan.

The last Saturday morning of being in a cock cage. There was going to be no more 5-year plans. Covid 19 made me realize how futile plans could be. I was now a free man literally and figuratively.

I thought I should enter the dating world. Being a 6, I thought of dating Felicity who was in my rating range. I had seen her twice when Andria exploded in on me. "Why are you dating that dog? Why aren't you dating me? I heard you even fucked her. You got out of your cage and you fucked her!"

I let her get rid of some more steam and when she calmed down, I tried to rationalize, "Andria, you are so far out of my league." (Cue Tal Bachman's song: "She so high above me").

"Let me decide that. I have loved you for so long."

"I have loved you too."

"Well give us a chance." We looked at each other longingly. I thought, 'You fool, just go for it.' I picked her up and carried her into my bedroom.

"Oooh, Harry. Are you finally going to do me."

"Time for talking and planning is over." Putting her down, I rapidly removed her clothes, then lightly tossed her on my bed. She bounced twice while squealing. I threw my shirt off and came closer to the bed. She lowered my pants then my briefs and my cock hit her chin.

"You fucker. You've kept this thing from me all this time."

"I said no talking." Then grabbing the back of her head, I pulled her luscious lips over my hardening cock. I let her oral ministrations proceed for--'Fuck the Mississippi's'--until I was crowbar hard. Pulling away and pushing her back, I dove down to her nipples. I sucked on them with determination. I almost gave her a Hickey but pulled away in time. I touched her cunt with two fingers and felt her very moist pussy.

I climbed on top and she reached for my cock to align me with her treasure. Her beautiful cunt. This was not the time for making love. This was time to release the tension built up inside both of us. Two years of tension. I pushed in, my crown finding some resistance. Then whoosh. Two inches pushed home drawing an "Aaahh," from both our mouths. I waited for her to catch her breath, then slowly pushed in at increments of two inches until I was fully immersed. I looked into her eyes. As much as I wanted to fuck the shit out of her, I knew enough to see if she was on the same page. She had an over bite on her bottom lip, looked back at me then smiled, "Fuck me!"

I started the slow withdrawal until the head had almost escaped then thrust home again. "Aaahh," she moaned. Not certain if she was in pain, I slowed down and her response was to grab my ass, wrap her legs around the back of mine and pulled. "Give it to me. Hard. Harder."

I didn't hold anything back then. I increased my strokes and also rotated my hips in the process. I put my hands under her ass and used the leverage for maximum power.

"That's it. Umph, Fuck me. Umph, Fuck me harder. Umph. Don't stop. That's it."

"I'm getting close. Harder. Yes. Yes. Fuck, I'm Cumminnnng."

I fucked her through her orgasm. Slowing down slightly while she finished. Then I resumed the power thrusts. I'm not sure how I hadn't already exploded but I knew I was close. "Andria, where do you want it?"

"No, Harry. This isn't the time for any planning. I want you to come deep, deep inside me. Let your animal out."

I should have argued but I wasn't in any state. My orgasm was coming fast and furious. I pumped even harder. I reached the deepest part of her cunt and exploded. My whole body shook as I shot 7 powerful blasts of semen inside her.

Then I rolled off of Andria and we both lay gasping. After some minutes, I leaned towards and said, "That was amazing. Easily the best sex I have ever had."

"Me too," she said between breaths.

"I didn't plan to cum in you."

"If I hear you say the word 'plan' one more time especially after such an amazing performance, I'm going to cut your balls off. Now get back here and fuck me again."

"I am going to fuck you so hard you won't be able to walk for a week, but first I am going to make sweet, sweet love to you." I looked her in the eye and gave her a soul-searching kiss. Make love we did; followed by fucking; followed by more love making. This was the start of our truly beautiful relationship. A 'real' boyfriend-girlfriend.

When we were sexually sated and were getting something to eat, Andria punched me in the shoulder, "You kept that beautiful cock from me all these years. I was wrong with my original rating for you. You are definitely a 9."

We had 2 months of a wonderful mind-blowing connection. One day she came home bouncing off the walls. "I have some great news. They want me to go out to Hollywood to audition."

"That's wonderful news. I knew you were going to make it big. I always believed in you."

"You are my biggest supporter."

"When do you have to leave?"

"Next Monday"

"Can your biggest fan come along. I have two weeks of holidays coming."

"Could you? With you by my side, it will give me so much confidence."

Two weeks later

Wonderful time. We had so much sex plus we saw the sights and then more sex. I helped her with her parts and readings. She got a small part in an indie film. She was over the moon.

I had to get back to work. We took a taxi to the airport; I had the taxi wait while we said our good byes. I held on to the car door for 4 Mississippi's when I had one of my best quick thoughts ever. It was an epiphany. Perhaps not having a 5-year plan freed my mind. A huge smile swept over my face.

"What is it?"

"I will call you tomorrow at 9:00 pm New York time and tell you." With a spring in my step, I entered the airport.

When we talked later the next day, she was so excited about her first day of filming. Then she remembered, "So what is your big idea?"

I told her. "I gave my notice this morning and they didn't want to lose me. They are transferring me to the LA office. I am coming out there next week to join you." She was thrilled. We made plans for me to bring out clothes and small things in my suitcases. I told her we had sub-let our New York apartment (giving us a safety net), "While you are filming, I'll find us an apartment there."