A Very Merry Time - Cover

A Very Merry Time

Copyright© 2014 by Pettybox

Chapter 2

Erotica Sex Story: Chapter 2 - Merriam and Hillary are roommates with little in common except they are young vibrant women who want to thrive in a sexual world. Hillary see's Merriam as missing out on some of life's pleasures and she strives to help her attain those. She leads Merry (Merriam) through the sexual rabbit hole of satisfaction in more ways than one.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Consensual   Reluctant   Fiction   Oral Sex   Anal Sex   Masturbation   Petting  

In the morning Merriam and I were typical to our habits. The first one up made coffee and after we each got a cup and began to move around we started talking.

“I thought about it.” Were her first words that Sunday morning, and that was after her first few sips of coffee.

I just looked up from my newspaper and coffee with a quizzical cat look.

She “answered” my look with, “I think about, umm ... How would I feel if Artie hired a prostitute to get the kind of sex he fantasizes about? You know, to find out what it’s like.”

Without looking up from my paper I asked “How do you know he hasn’t”

I could tell Merriam was burning from my comment and she let it hang in the air for a few minutes and finally said, “That was mean.”

“I’m sorry Merry but how DO you know it isn’t true? Your dating Terry for a weekend is not like hiring a stud service. Anything that happens will be voluntary and he will have no expectations. Terry is a great guy who happens to know his way around a woman. He loves the hunt and the chase. No matter what, you’ll meet him Wednesday night here for dinner.”

“You invited him to come meet me?”

“Nooooo. I invited him to dinner. He’s in town every Wednesday for a sales meeting and I asked him to stop. He asked if we would be alone and I told him my roommate would be here. He asked about you and I simply said you had a guy who was serious about you but you didn’t quite know what to make of the commitments. I said you were in a rut and needed a night away from it all. That was why we were staying in. We could eat, drink and talk, may be watch a movie.”

“Is he going to stay with you afterwards?” She asked suspiciously.

“No, he and I are friends, not lovers. We had our little fling and sex now would complicate our friendship.” I assured her.

For the next few days we both went about our workaday lives and we carried on as we normally did. Tuesday was a date night with Artie for Merry but she was home before 10 and she came in and sat to watch the news with me and I couldn’t help but notice the sour look on her face.

“What’s the matter roomie?” I asked.

“I’m very confused and feel a little betrayed, I guess is the word.”

“Not by me, I hope.” I countered, but she quickly shook her head.

“No, after pizza we were going to the movie and he had to stop at the hotel where he works to drop off some keys he had, something about Fire Department inspections. When he got back in the car I sort of went for him, tried to get him to skip the movie and we could use one of the rooms. He looked at me like I was out of my mind and told me he REALLY wanted to see this movie. Probably the first time I’ve ever made a horny come-on to him, he usually sets the pace, and I get shunned for a movie. I didn’t say a word the rest of the night and I’m not even sure he realized it. When he dropped me off he turned off the engine like we might neck but I just leaned and kissed his cheek, saying I had to run. He just said OK and started the car. He never ONCE made notice of the fact I ignored him from the hotel to the theatre, and all the way home.” She said as she began tear up.

I wanted to go over and hug and comfort her, but I was afraid she might take it the wrong way right then, but I did have some advice for her.

“Merry, like I’ve told you before, make sure of the commitment you want to make. Don’t mistake love for complacent security. Making sex a bigger part of your relationship is important. Besides bearing your own children, it may be the greatest joy in life, and all you need to experience it is a partner, preferably the person you love, intimately, privately, and without reserve.”

“I think I understand that more now, Hillary, and tonight I tried and struck out. I just got the first picture of being married and I’m sure discouraged. It’s not looking like the bliss I expected.” She said with a sad face.

“Well, Merry, you can’t let one night like tonight color your whole perspective. Men can have off nights just like a woman does. Don’t think this is what every night would be, that wouldn’t be a fair judgment. But I think you may need to light a fire under him sooner or later.” I advised.

“Ummm, do you really think that if I spent some time with your friend I might see things differently, get a new perspective?”

“You would definitely see how another man might treat you, and not take you for granted.” I said hoping to make my point.

“That’s what it is, isn’t it? Artie takes me for granted already. I need to show him some zing, something to make me sexy, mysterious and unpredictable.”

“YOU said it. I think you have finally seen the light. You see, I’m not trying to push you away from Artie, I’m trying to push you closer in a lot of ways. You know the reasons you love him, now you just need to learn the things to keep falling in love with him, and he you, over and over. If I showed you one thing, it’s the joy you can get from your own body, and now you have to share that.”

“I guess I finally know what you mean. What have you told this Terry guy?” She asked.

“Exactly what I told you before, nothing more.” I said crossing my fingers to cover a “little lie”.

I had told Terry she might be open to getting away from it all, but beyond that, I made no promises or gave him false expectations. I also knew he was planning to bring his boat to Cape Cod. He planned to go down the Hudson to New York, through the Long Island Sound and to the Cape. When I say “his boat”, it’s more like a huge yacht. Terry’s family comes from Sanibel Island money, his grandfather specifically, and Terry was entrusted with keeping the yacht fit and in order. He keeps it in Martha’s Vineyard or around Albany for the Summer & Fall, dpending on his work, and then leaves it back in Sanibel for the Winter & early Spring... “Keeping” the boat is an expensive proposition, but he enjoys parties on it during the summer.

I really wasn’t sure how Merry and Terry (Oh God! I hope they NEVER become a couple!!) might get along. I know Terry would like how Merriam looked, but he wasn’t real superficial. If she were homely, but was fun to be with and a good personality match, it would make little difference to him. (I also knew that once he saw her with tits out he might go crazy, if there were one Achilles heel in his make-up, it was breasts, and she had the kind that any breathing human might want to get their hands and mouth on)

Until Terry knocked on the door Wednesday evening Merriam and I hadn’t discussed him anymore. For her it was general nervousness because she was seriously contemplating doing something impetuous and morally challenging to her own make-up. Merriam chose to make an entrance after Terry and I exchanged hellos as he presented a hostess gift of wine and flowers. I was about to take the flowers from his hands when he turned to the now entering Merriam saying, “And you must be the afore to mentioned roommate that I have never had the pleasure to meet. Hillary said you were a bit down in the dumps and I hoped these might lift your spirits so we might all have a grand evening.”

Merriam turned crimson and accepted them, introducing herself.

“Merriam, call me Merry.”

“Enchante’, for sure. Terry!”

“The flowers are beautiful and YES, they will lift my spirit.” She said as she smelled their fragrance and already felt at ease around him.

We sat and talked over a few glasses of wine with some cheese fondue appetizer. He had been there for about an hour when I said, “Well, I’ll leave the two of you to talk while I put the finishing touches on dinner; I just need to brown the casserole and sear the scallops.”

After I went into the kitchen I was happy to hear the two of them talking up a storm. If Merriam turned him down, it wouldn’t be over discomfort of getting along. They were laughing and at one point she came back to get a second bottle of wine. She only winked as she came by.

I said, “10 more minutes.” And she answered “Take your time.”

I was happy for her.

When I had the scallops just right I was about to call them to the table and I became aware it was quiet in the living room.

I called out “Dinner bell, come and get it!” and turned to walk the serving pan to the table and I saw a quick reflection in the ocean picture opposite the dining room table. They appeared to be breaking from an embrace.

At the table I could see Merriam was wet-eyed and Terry said he was going to wash up.

“Everything OK?” I asked.

“Yes, he just hit a couple nerves as we did a little due diligence on our situations. I’m fine, he’s IS a sweetheart. (and then under her breath) “and a good hugger and kisser too”.

I was happy she had opened up a bit to Terry, but surprised it happened so fast and so physical. (Que Sera Sera.)

“I told him love had confused me and I started tear up and he hugged me to comfort me and for some reason I just kissed him and, Wow, did he kiss back!” She whispered as we heard him coming back up the hall.

Merriam moved up to take a chair as I went into the galley at the dining area as Terry walked around the corner.

“Let me get your chair, Merry.” He said as he pulled out a chair as I turned to bring in the scallop platter.

“Here, Hillary. Let me get that casserole if that’s all we need.” Terry said brushing by me.

“Great!” I told him, “That’s the whole dinner. Just bring in the wine from the living room.”

He ducked around the corner and came back filling our glasses before he sat.

I rose my glass to make a toast and he quickly said, “To friends, my two beautiful friends, one old and one new. Here’s hoping our new acquaintance together tonight brings a lasting memory.”

“Terry,” I added, “You are such a charmer, but a gentleman through and through.”

We talked about literally everything over dinner, but it was quite apparent that Merriam had been charmed by Terry. The way she watched him as he spoke told me she was smitten. I felt I should be the one to center her a bit.

“Merry, had you told Terry that you got engaged last week?” I asked knowing it might let some of the air out of her balloon before it got out of control.

“Yes, she had.” Terry answered quickly. “But he hadn’t put a ring on her for the question. As she explained that to me she got a bit emotional, so let’s not throw a blanket on this nice moment.”

“Of course, I’m sorry.” I said shifting gears, “Had you told her you’re headed to Martha’s Vineyard this weekend?”

“No. Ummm ... Merriam, my Grandfather has this yacht that he’s entrusted to me. It’s been my sort of floating party from time to time over the summer, but I’m going to take it down the Hudson, through Long Island Sound and into The Vineyard to keep there until I bring it back to Sanibel, come the Fall, for the Winter. I leave on Friday night and I’ll get there sometime Saturday after mooring at Port Jefferson overnight. It will be an awesome trip. I’m looking forward to it.”

“A yacht? How big is it?” She asked.

“Tip to tip, it’s about 65 feet. It’s something I could never afford and can just barely afford to just keep it in the water. It’s was his pride and joy, but he can’t sail it anymore. Once he passes I’ll probably sell it. Don’t let that sound so crude. It probably costs 20K a year to gas and stow it. He insures it; otherwise I could never have accepted it. He’s tickled to know I enjoy it so much, but if I’m on it 20 days a month from April to October, it’s a lot. I’m toying with, and tried mooring here and living on it some times.”

“Sounds like a job to just drive it, or sail it, however boat people say that.” Merry said blushing that she didn’t know the term to use.

Terry smiled big at her. “I’d like to tell you how I can deftly move this small ship in the water but, outside of short party trips on the Hudson here, or right around the inlets around Sanibel Island, I can’t use it safely. I hire a pilot who’s able to get me around places like New York and Long Island and knows how to keep us from getting lost out on the ocean.”

This was all new to me as well as Merry and I had a lot of questions too.

“That alone must be expensive, hiring someone to ... umm... “pilot” the boat.”

“Not as much as you might think. Many of these guys work out of Cape Cod, Sanibel, and places like that making one-way trips, but they need to get back to their base or next job. I usually check a list of guys looking to make returns on a schedule. It saves them the expense of flying, and they make a little.”

“So the tail wags the dog as to when you can make trips like this.” Merriam asked.

“Yes, I schedule my trips around them, except when I fly to Sanibel in the Spring to bring it back here, but I can usually find a few snowbirds needing ferry back to New York and that defrays the cost.” Terry said as he dug into his dinner.

“What are the accommodations when you do this?” Merry wondered.

“It has 3 sleeping quarters, all with queen sized beds. There’s a kitchen, sundeck, living room, 2 toilets, and one fresh water shower. When business brings me here I live on it when I can for spring and summer.” He added as he got up to pour more wine for all of us.

That move changed the subject of conversation away from him back to current events and things going on in our lives, our jobs, etc. After dessert they both helped me clear the table and get things in the dishwasher before we settled in the living room, all three of us on the sofa with Terry in the middle. He brought a DVD of “Walk of Shame” that we watched and giggled our way through. The food and wine had really lifted our spirits and I knew Terry was setting his sights on Merriam, he was interested and Merriam was showing me a side I had never seen before, a little teasing and playful.

I got up to go to the bathroom; I was about ready to burst. When I came out I opened the door as quiet as I could so I could peek and see if they were making progress as a couple. Terry appeared to be facing Merry on the sofa with his mouth firmly attached to hers. I watched them neck for a minute and then noisily reopened the door. They broke and I rejoined them on the sofa flipping through channels to find the news, it was just eleven o’clock.

“I have a 7:30 breakfast meeting and should be going.” Terry said as he stood and I agreed that we ALL had to work in the a.m.

I stood and stepped into Terry’s arms for a hug and kiss and then Merriam took his hand and walked him towards the door. Terry said how great it was to meet her and then kissed her and turned and waved to me as he left.

The door clicked shut and Merriam turned to me. Her faced turned white and then red.

“I just agreed to go with him on his trip. We leave here Friday afternoon and come back on the train on Sunday evening.” She said as her face burst into a wide grin, but I could see tears as well.

“What’s the matter Merry?” I asked.

“I’m really going to cheat on Artie, and I really don’t give a shit.”

“Merriam, if you really didn’t give a shit, you wouldn’t be so confused right now.” I pointed out to her.

“I suppose, I just have to make up a good story for Artie.”

“Merry, he doesn’t OWN you and you don’t have to explain every little move you make. Make him squirm a little and maybe he’ll appreciate you more.” I advised.

“I have to tell him something, I’ll just say I’m going on a shopping trip to Boston or New York with a girlfriend.” She said, her voice trailing off.

“How did Terry ask you?” I wondered.

“I had turned to say something to him and I couldn’t resist kissing him again. He got right up on to me and threw his tongue down my throat and then hugged me tightly and whispered in my ear. He said, “Come with me on my trip this weekend. You can get away and clear your head about things. I’ll have no expectations but to show you a good time. The weather is supposed to be awesome, we can laugh, talk, swim, sunbathe and have a couple great dinners in Port Jeff and Martha’s Vineyard.” I just said OK, but to call me tomorrow here.”

I cautioned her to think about it before jumping into this because I had to warn her, Terry rarely followed up after an affair. He’s a hit and run guy, but he’ll stay friends if you don’t stalk him.

“Know that if you think you’re going to start something beyond the weekend, he will likely not have any part of it.” I cautioned her as I saw the smitten look on her face. (Terry was as advertised, VERY charming, and hard to resist.)

“I know, I told him the same thing about me. Whether I marry Artie now or later, I still think I’ll be with him, but there is still no ring on my finger.” She responded showing me more awareness of the situation at hand than I gave her credit for.

After a long silence she looked at me and then hugged me tightly and then kissed me on the lips, a little kiss that lingered a bit.

“No more talk about Terry. I’m a big girl and you passed a baton to me in Terry that I can take and run with, but I know that no matter what happens, I pass it along at the end. I didn’t have time to ask him a lot of questions, but there are separate beds and quarters. He assured me that nothing had to happen, even though we lit some fuses here. Thank you, you are a special friend, and I love you in a way I’ve loved no other friend. Maybe someday I’ll make love to you to show you how I feel.”

She spun from me and went right to her room. The wisdom she picked up in the past few days was apparent and I wondered if the orgasms I gave her unlocked some roadblock in her mind, or if this was all just coincidence as she put her relationships with Artie, me, and now Terry, in perspective.

True to her word and my own promise to her, we spoke no further about Terry, her possible weekend, or Artie. Upon returning home from work on Friday I saw she had left me a note, “See you Sunday! XXXOOO.” Her car was gone leaving me only assume she had went with Terry.

I heard nothing from her all weekend and at one point I called her cell only to hear it ringing in her room. She had left it behind with a message on it that she would return calls.

I checked train schedules and saw there was one due from Boston at 6:45 on Sunday evening. At 7:30 I heard her car pull into the car port across from the townhouse. When she came in she seemed to be a different person, happy and carefree. She was no more in the door when she picked up our phone and called Artie, bubbling on the phone about her shopping trip and how she could not wait to see him. When she turned and looked to me, (we had hardly said hello’s when she had walked in) and she smiled big, blushed deeply and then wheeled her bags to her room and closed the door.

I waited about 20 minutes and finally I was dying to know how it went and I went and knocked on her door.

“Give 10 more minutes, I’m still returning calls.” Then I heard a loud giggle. “Why do you want to talk to me?”

Then, in my best George Costanza I barked, “DETAILS, BABY, I NEED DETAILS!!”

I heard her giggle again and I went to the sofa with 2 wine glasses to wait for her.

True to her word, in about 10 minutes she came out and she truly glowed.

“You don’t think I’m going to kiss and tell, do you?” She said mocking me.

“You bet your cute ass I think you are. Come on Merry, spill!”

“OK, bear with me a little. I’ve never shared like this before and some of it’s a little embarrassing, and some is a LOT embarrassing. You NEVER tell anyone this, UNDERSTOOD?” She said pointing her finger.

“You KNOW who you’re talking to Merry. We’ve shared intimacies for the sake of your personal happiness and we have a bond. Be sure of that!” I assured her.

“First of all you could not have found ME a better person to trust my both personal and sexual well being. Terry is a gorgeous sweetheart and could have not been and nicer, and sexier, and more patient, and probably most of all, understanding. He and I will be friends for a long time.”

“The boat is fucking huge! When he walked me to it on the Capital Boat Club dock, I thought he was kidding me. He brought me up to the pilots nest and asked me to stay with him until we picked up his hired pilot in Croton-on-Hudson. The whole idea of being with him had me horny as hell, and I was pretty giggly. We had been on the water for about an hour when he asked if he could quiz me on something that was very forward. I shrugged my shoulders and said “shoot.”

“You’re all giggly and squirmy, I have a feeling your little pussy is begging for your attention.”

“I was flabbergasted, but, just to show him that I was “in” on the weekend. I admitted he was right!”

“Pull up your little sundress and have at it, don’t be shy. Just because I can’t help you right now, doesn’t mean you can’t do what feels good.”

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