A Very Merry Time - Cover

A Very Merry Time

Copyright© 2014 by Pettybox

Chapter 4

Erotica Sex Story: Chapter 4 - 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  

As late September rolled around I woke on a Saturday morning after having a long late night fuck session with Caleb. He had to fly out early and dressed and left around 5 a.m. I got up with him at 4:00 and showered with him, but only because he said “we had to talk”. He was going to his main office to get details on a promotion that might stabilize him more, as far as travel went. Where we were once an “item”, seeing him once or twice a month was no way for me to have a relationship. So, ravaging each other bodies from time to time kept us “current” with each other was the extent of what we had. We seemed to mutually “use” each other. This morning in the shower he admitted something to me and had caught me by surprise.

“This meeting I have today in Minneapolis was not called, it was set up by me. There’s a position open in New York that I feel qualified for, I want to be considered for it because I’m finding it harder and harder to be away from you. We always say that we tried love, but it didn’t work. I think we both know we were kidding ourselves. We both couldn’t face a long distance relationship. I can love you again if you let me, or at least try. If not you, I can begin to settle down a bit, but I think we can make something of the long sex sessions we have.”

He tried to turn me towards the shower wall to get in me, but I resisted, not fully understanding his words. He seemed he wanted to try and make something of “us” again, but I didn’t know if his urgency to want to fuck me right there and then was passion, or if he was just being re-horned by showering with me. I think he thought he was being sweet; I was leaning toward feeling used, as I had done gladly and voluntarily so many other times. Don’t get me wrong, I have feelings for him, but it was always about sex, that was beginning to bother me once I had been satisfied the night before.

Overall though, I was sort of knocked out by his words. YES, for sure there was a time when we had a great thing going, but at the time he never seemed to understand that I couldn’t sit around and wait for him to show up every 10 days, or two weeks, whenever the job brought him back into the area. We had a little fight, or disagreement, about it and didn’t see each other for a few months, but then he sent me an email saying he was going to be here in Upstate for 3 or 4 days and he wanted to see me. We screwed like honeymooners for each of those nights, it was actually just before Merriam moved in. Since that time, if he’s going to be in town he clears his nights, as I do, and we have a “date”. He is very special to me, but I have always wondered about his total commitment. I don’t “like” whoring around whenever I get that urge, the one that my fingers can’t seem to scratch. I have other “fuck buddies” I can utilize, but none are candidates to be anything serious. I really am willing to make a commitment to Caleb, but the first time I think I’m just his sperm receptacle whenever he happens to be around, I’m done for good. For the 3 or 4 years he’s been out on the road how do I know he doesn’t have a “Hillary” in lots of other cities?

As I laid there I was glad I had showered with him, if only for feeling clean and changing the sheets before I went back to sleep. I was beginning to have it in mind that later today or tonight I might get a few of my toys out and have a Hillary Solo Sex Day. I’ve always fantasized of going out and picking up a woman and bringing her home to fuck, much like Merry; someone young and inexperienced, near virginal. In truth, I would NEVER do that, but it played in my fantasies when I had my Hillary Days. I was just about to touch my pussy as my clit began to connect with my thoughts when I realized I was smelling coffee. Thinking I was alone I bounced up and threw on my robe and went out into the living room.

“Hello sleepyhead!” Merriam said as she looked up from her Kindle.

“When did you get here?” I asked as I walked by and touched her cheek on my way to get coffee trying not to show my shock of her being there.

“About midnight, I heard you playing and quietly went to bed. I fell asleep to the sound of your orgasms and pleas for more. I hope it was Caleb, because you called his name out more than once.”

“It was. Did you hear him leave”

“I was aware of something going on. I thought it might have been Round Two. But I fell back asleep before there were any fireworks.”

“Did you and Terry fight?” I asked.

“No, we just got drunk,” Merry said with a smile. “Neither of us could drive so we got a cab. He had them bring me here and he went to his mothers so she could drive him to his car this morning. I don’t like staying at his Moms. Besides I haven’t been here in a week and I missed seeing you, having my morning coffee.”

“You’re going to move out, aren’t you? I mean permanently, right?” I asked.

“No, why do you say that? I have no motives for being here, besides wanting to see you, and avoiding his Moms house.” She insisted. “Did YOU two fight? Something’s got you in a mood.”

“No, I’m sorry. It’s just I was going to lay down the gauntlet with Caleb soon, and he aced me this morning by telling me he wanted to live closer so we could take up again, you know as a couple.” I explained, being sure I didn’t seem too excited about it.

“So, what’s wrong with that? I thought you would like that.”

“I wonder if there aren’t LOTS of Hillary’s all over the place.”

“Did you ASK him that?”

“No, that would show I didn’t trust him.”

“Apparently you don’t.” Merry surmised.

“Oh, let’s change the subject. This one gives me a headache. If I know I’m the only one and he’s here more than once a month, more than once a week, I could be in love with him. I just can’t take the constant tease of it all.”

“Tell him that!” She said.

“That might chase him away.” I insisted.

“For God’s sake, listen to yourself. You each need a dose of honesty, with him AND yourself.”

“OK, OK.” I said waving my arms. Change the subject. I’ve got some confronting to do with him and I don’t want to hash it out on my head right now.” I said exhaling hoping the subject was dead for now.

There was a minute or more of silence, just the sound of sipping coffee before she spoke.

“I think I want to spend the rest of my life with Terry. He’s just a part of me. We are so happy.”

“Good sex doesn’t hurt either, does it?” I asked as she turned 3 shades of red.

“N –n-n-n No, it certainly doesn’t and I wouldn’t talk to anyone but YOU about that. You know us both so intimately. I can’t get enough of him, and he can’t get enough of me. Those nights I spend here I end up with my hands in my pants until I fall asleep, I miss him so. You know, he asks me if we get together when I stay here. That pisses me off that he would think I’d cheat on him, but he asks like it would be OK. I told him cheating was cheating, no matter what.”

“Well, you can tell him that I’m not a stalker and what HAS happened between us was just rite of passage into sexual womanhood. You are the last woman I’ve touched, or who has touched me. Be sure he knows that and the last that occurred was the night you came back from Cape Cod on the train.”

Merry blushed and said, “He doesn’t know about that night.”

“Well, no matter. He knows I helped you shave your cookie, and you said you admitted I ate you. I remember you said that.” I recalled to her.

“I think he thinks we lived as lovers.”

“He can’t think that, he knows we’re both straight. Remember, he and I have an intimate relationship, not as lovers but as friends. We would tell each other of our experiences and giggle to each other.”

“I’m not trying to gain an advantage in my relationship with him, but just how did you meet him, and what made you so special?” She asked.

“Merriam, after all we’ve had you don’t trust m...”

“MY GOD NO! I trust you more than I trust anyone, including Terry. Your word is ALL I need. I am jealous, or should I use the word envious, of THAT particular intimacy you share with him. Has he told you about ALL that he and I share?”

“No, he isn’t like that with me at all. He would tell me of certain conquests, how he met and seduced them, but never names and you should know that from the very start with you, he never saw you as anything but “special”. I do know that from the night here to have dinner with us, where he met you, he thought there was a connection and something very special about you. I’ll tell you this, and if you ever disclose this to him, I WILL feel terribly hurt. He felt a deep sexual connection to you, and felt it was returned from the moment you met. From the few things he told me about meeting and getting to know you, and coordinating what you also told me in detail, about that first day on his boat, he perceived and almost smelled your sex, he knew you were aroused just being near him. He said he was shocked when you answered a challenge he gave you and did something he knew you never would have thought to do on your own. His suspicions of a special connection were proved to him then. He knew you were all in for EVERYTHING.”

Merriam sat and heard my words and looked to me and nodded, like she knew, but I knew too and spilled my thoughts, “You were sitting looking at him taking in his words, his aura, his vibration, and you got turned on, like it hadn’t happened to you before. He knows the signs when a woman is ready, and you hadn’t even “played” so far that day. He told you to relieve yourself and I know, and you know just as well, any other day in your life you would have slapped him and thought of jumping from the boat at such a suggestion. But you, who had rarely even taken care of that business alone, showed him just how you did it and when he was so close, you charmed him to make love to you and you obeyed everything he asked.”

Merriams face glowed for a moment and then declared a realization that made her overjoyed.

“He wasn’t being my sex teacher, he was really responding to his feelings, he really felt something.” She said in a low voice as if to make sure it sounded right to her.

“Yes, he told me that. He said for once he wasn’t with a woman who wanted to have an affair to pack away and recall in her intimate thoughts alone, he had someone he really cared for and he was almost sorry it was progressing so fast, because he knew it had to end, because of your engagement.”

“I felt something right away, but I took it as my being so innocent and willing to open myself, it was a combination of fear and wanting the experience, you know after what you showed me.” She said in a low, almost mousey voice, like she was embarrassed.

“How did you meet him? What made you different, besides not hounding him?” She wondered.

“I was having lunch with Marcia, a receptionist from another dental office in the Tri-County Medical Complex. She had called me about a job opening up in her office and she wanted to know if I was happy. We ate and talked outside at a sidewalk bistro and Terry came up because he knew Marcia. She introduced me and then they talked for a few minutes. All the while they talked he was giving me the once over with his eyes, and his smile brightened each time our eyes met. After he left she told me he was a player, but had a yacht, an airplane, and homes all up and down the coast. She said she dated him once, and then she paused and blushed, saying it was actually a weekend, but he hadn’t called her since.”

“I didn’t know what to say and was about to say something to break the mood when she added, “but, he always falls all over me whenever he sees me. I can’t figure him out. He has my number and knows where I work.”

“So anyway, I was happy where I’m working and had no interest in the job opening and after lunch we walked back to the Medical Complex where we work. She went to her building and as I walked to mine Terry was sitting on the bench in front.

I smiled and he said he needed a dental cleaning and saw there was a dentist right there and wondered if I worked for him. I said that I did, but wondered why he didn’t go to Marcia’s office? He said it was because I wasn’t at that one, then he came up and made an appointment for a cleaning, we got him in the next day. He flirted all the while I worked on his mouth and when I finished he asked if he was fit enough for a date. I smiled because he had me wet with his flirting, and he knew it, and I accepted.

We went to dinner and a movie and came back here. As much as I wanted to do him that night I resisted, even though he had half my clothes off. As he was leaving he told me he had tickets for Van Morrison in Boston that weekend and then Jerry Seinfeld at the Comedy Connection there the following night. He said he had a suite at The Marriott Long Wharf. I nearly jumped out of my drawers to say YES with great excitement, but instead I asked him, “What are the sleeping arrangements?” He said they could be “whatever I wanted and he would respectful of my wishes.” I just said “We’ll see.” I played with myself for half the night after he left.

Early Saturday morning we trained to Boston and had a great time talking and sharing thoughts on the way. At one point we necked in our seats, and I was soaking wet. We walked from South Station to the Long Wharf where we had half a day to kill before the show. I could resist him no more. You can guess the rest of the story.”

“Then later you doubled with him?” she asked.

“Yes, but not intentionally. My friend DiMaria said she was flying to Lake Havasu with a guy and he offered that she could ask another couple. Caleb was in town so we went. When we saw it was a private jet, and TERRY was the pilot I near died. Only he and I knew that we had history. He flirted with his eyes all weekend with me and never got caught. Actually the four of us ended up on a boat partying naked with all the college kids around. At one point we drove off to a somewhat secluded spot on the lake and had sex, no serious swapping or anything like that; just them on the fore of the boat and us in the aft. However every time I looked towards them, he was grinning at me. They eventually came to our side of the boat and we screwed side by side in the hot tub, and DiMaria and I played a bit with each other while doing so. About two, maybe three months later he called me and asked me to go skiing in Vermont, there was early snow in Killington. I think we made but two runs from Friday night to Sunday night, but kept real busy. After that he would call and stop over and we would talk, have dinner, coffee, drinks, whatever, but he never made sexual advances at me and took me into his confidence about girls he was dating, and how they all wanted him for their own.”

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