Perspectives Series: Jess Pt. 01

Martin's wealth didn't seem to bother Simon at all. The way Simon spoke of Martin, I felt he pitied him more than he envied him.

Simon described the home to me on the way to the party. He had helped Martin and Teresa get settled. The most stunning feature of the home was the outdoor private patio area. It featured a heated, zero horizon pool, outdoor oven and grill, fireplace, built-in flat screen TV, and large planters of flowers and trees lining the massive wall that surrounded it. The house sat on a hill, so this area was completely hidden from the street and from the neighbor's view. According to Martin, the patio area had been featured in Architectural Digest a few years earlier, when it was first constructed.

I wondered at why Martin had decided on a party in May when it was still too chilly for swimming. The real nature of the party and the guests attending gave me my answer.

It took us nearly 30 minutes to get to Martin's home. We were greeted at the door by Teresa. I had met Teresa on my second date with Simon. She was the one who told me that Simon was a monogamous dater. I hadn't heard that term before, I remembered, but I recall that it made me very hopeful.

Teresa was striking. She had long, dark brown hair and green eyes. She stood maybe around 5'7 or so, but it was hard to really know because she always wore heels. Her body was fantastic, with long, slender limbs and a delicate, elongated neck. She seemed to float when she walked, and I found myself casting several coveting glances her direction as she mingled throughout the crowd. I wasn't attracted to her, exactly, but more attracted to the overall feminine look she had.

Although Teresa was the live-in girlfriend to Simon's best friend, she wasn't as friendly as you would expect. She had a distant way about her and you got the clear impression that she was just going through the motions with Martin. One time, after Teresa had walked past us, Simon started to say something to me in my ear but stopped. I wondered what was on his mind, but I didn't ask.

There was one other couple there that I recognized from the earlier party. Actually, I recognized her but not him. Jill was lively, and by far the friendliest of Simon's friends. She made me laugh out loud and I could just talk to her for hours. She had reddish hair and the personality to match. I felt instantly at ease with her. I wasn't sure how Simon and Martin knew her, exactly.

Simon stayed by my side the entire evening. He whispered to me that most of these people were business associates of Martin's and that a couple of the introductions that evening were crucial to Martin's future ventures. At one point, I spied Martin talking with a couple of gentlemen away from the rest of the crowd. I have been involved in enough business deals to recognize one when I see it. From what I could observe, it was going well -- both parties were engrossed in conversation and Martin began to stand taller, indicating he was pleased with the progress. You learn to read body language like that when you work in sales.

After two hours, the party had thinned significantly and Martin's would-be-business-partners were gone. Martin turned his attention to Simon and I, and we walked through the house on an official tour. Simon hadn't seen the house all put-together, and that was my first visit.

We were in the basement while the remaining guests were in the kitchen, upstairs. Martin's cell phone rang and upon reading the caller ID, he excused himself to answer it. I suspected it was regarding the recent business proposition he was working on. Simon slid behind me with his arms around my upper body so we could look in the same direction at the same time. We were talking about the layout of the room, what we would do differently. Very casually, as Simon was accustomed to doing, he slid his hand into my blouse and onto my breast and began fondling it. He kept talking about the room and surveying it, and when we pivoted around to look back toward the bar area, Martin was staring at us. He kept talking on the phone and he didn't look surprised or phased, he almost seemed to be looking through us.

The gesture started out as being very non-sexual, but intimate. When I became aware that Martin could see what Simon was doing, it changed for me. This made me feel uncomfortable, and discomfort had become synonymous with arousal for me. Martin continued talking on the phone but quit pacing around, and instead, remained fixed on our position.

Simon could sense my arousal and so he played along. He lifted my skirt with his left hand and started stimulating my clit while fixing his gaze on Martin. I also had a fixed gaze on Martin and the sight of him watching me was titillating. Simon had become even more skilled at bringing me to orgasm by that time. As I had become more comfortable talking about how I felt and what I liked, Simon was learning, too. As I recall, Simon and I hadn't had sex that week, and so it was very easy for him to expertly lead me to orgasm. I came violently while looking directly into Martin's eyes.

Martin was still on the phone and Simon didn't say a word. He pointed my shoulders squarely at the door to the bathroom and lifted my skirt to pat me on my bare bottom. I trotted off to the restroom.

When I emerged from the room, Martin was off the phone and was engaged in conversation with Simon. I couldn't make-out exactly what they were saying until I got a little closer. They were talking about Martin's business deal. From what I could tell, they were well into the conversation.

As I stood there with them, my mind began to wander. What is going through Simon's mind? Is this his way of saying to Martin, 'you may have all this, but you don't have Jess'? Does he derive pleasure from his best friend seeing him please his girlfriend? Is this the first time he's done that? Oooooh, the last question was almost just too much to think about. They did go to college together, and I bet there were some wild nights.

I finally just decided that the truth is this: We may never know what goes on in someone else's mind. Even in the head of someone so close to us.

Martin continued the tour and acted like the whole thing never happened. By the time we got upstairs, I just started laughing incredulously to myself and then partly out loud.

A few more people had left and there was only one other couple remaining, saying their goodbyes to Teresa at the door as we topped the staircase.

The four of us walked into the living room and sat down. It was the first time I got a good look at it. The entire party had congregated in the living room, making it impossible to get a good look at the place. Martin settled into an oversized chair and spread his legs for Teresa to sit in front of him. Martin and Simon carried the conversation, talking mostly about business. Martin's hand rested easily on Teresa's inner thigh and I thought I noticed him moving his hand up her skirt a few times. He fondled the pendant on her necklace, but I couldn't see what it was from where I was sitting. Teresa only spoke when spoken to.

On the way home, Simon and I talked about Martin and Teresa, the party, and the business deal. If all went well, Martin would be investing in a shoe company of sorts. It didn't sound like a good deal to me but it wasn't my money, and I didn't really know much about it, nor did I care. Simon's manner of discussing Martin and Teresa was very detached, like they were distant acquaintances and not close friends. He never really said that he didn't like Teresa, but I got that impression. Or more accurately, I got the impression that he didn't respect Teresa.

The second significant event in our lives those first few months was more personal for me. Simon and I spent a lot of time becoming more intimate. Part of that intimacy included feeling completely open to his touch. I had already proven, I felt, that I was comfortable around both strangers and friends (Martin, anyway). But my boundary was with parts of my body. I was still very nervous about anal sex of any kind.

At first, I wanted to dismiss this as just one of those fantasies all guys have that they've picked up from porn flicks. I didn't think it was that important to Simon, and eventually I came to know that the act, itself wasn't. What was important to Simon was my commitment to complete intimacy with him. Simon felt that as long as I had boundaries, so our relationship would have boundaries. I truly didn't want that, but I needed help and guidance in that area.

So I did what any intelligent adult would do. I searched the internet. Google produced a list of good anal sex resources and I learned great tips. Lubrication was the big key to success and you just can't have too much. Starting out yourself with one finger, and then two, was another tip. There were health tips, cleanliness advice, toy recommendations, the list was endless. Many of the women reported having the most powerful orgasms of their life during anal sex. This was of particular interest to me, as I had not imagined this might actually be enjoyable for me. The possibility of pain was first and foremost on my mind. I felt I was ready to do something to try.

Simon and I talked about it. I told him what I had learned and that I really, really wanted to share that with him, give myself to him in that way, but I was afraid. At that point, I was at least willing to think about it some more, and to keep talking to him about it; fully realizing that it might take me a long time to get over my own prejudices. My lack of commitment to the idea was not pleasing to Simon, but I think he looked at it as another opportunity to guide me in the right direction. I think it really disturbed him how much I was upsetting myself over it.

"I'm in no hurry -- I can wait as long as it takes for you. But I have to tell you that you're not going to solve this by intellectualizing it. You can't think your way through a major step like this, you have to ease into it, feel it."

His words were absolutely true and he said them very matter-of-factly, as if I should just be able to perform this simple task.

Finally he said, "You know everything you need to know."

I thought about those words for a long time, 'I know everything I need to know.' What do I know about this? What one thing has to exist for this to work? Is it desire? Willingness? Relaxation? I wasn't sure.

It was perplexing me. I was having trouble coming up with answers on my own. Simon pulled through for me, as usual.

One Saturday afternoon, Simon brought a gym bag into the bedroom and placed it on the floor. He bent me over the footboard of the bed and tied me to the posts. He tied my ankles to the legs of the footboard. Then he began unpacking the gym bag so I could see the contents. There were three separate brands of lubricants, an anal plug, an anal vibrator, a douche, and a string of balls in varying sizes. My eyes widened as he placed each item on the bed for me to see. Lastly, he produced a blindfold and placed it over my eyes.

My heart began to race. What is he planning for me? He first touched me on my back and I flinched. I guess I was so tense that it startled me. I could hear him leave the room.

About five minutes later, Simon returned. He touched me on the same spot on my back and I didn't flinch that time. He started rubbing my back, and as his hands approached my buttocks, I began to tense. He immediately withdrew and left the room.

Another 5 minutes passed, and he started with the same spot on my back, working his way to my buttocks and massaging them. Each time I tensed up in any way, he left the room. He gradually worked his way up to administering lubricant to my behind and by the time he got to massaging my well-lubricated hole, I was more aroused than frightened.

He took off the blindfold and released my wrists and ankles. He had used none of the tools on the bed except the lubricant.

"Do you know what it is, now? The thing that you already know."

I knew it immediately. Trust. That was it. I just needed to trust him.

"Trust?! Trust is all I need to know?"

I looked to him for approval of my epiphany. His smile lit up his whole face as he leaned in to kiss me.

Knowing the answer was the easy part. Next I had to feel it.

Chapter 12

When something is hanging over your head as needing to be done, you can think of little else until you complete the task. I think I had become obsessed with this one thing. Simon and I talked about it a lot and the more we talked, the more comfortable I began to feel. I think Simon wanted the whole act to be over with, mainly to stop my obsessing. He never grew impatient in any way, but I sensed that he felt a bit guilty about how it was affecting me.

One evening during the week, Simon and I were in bed in what started out as a pretty ordinary lovemaking session. I was stroking Simon's cock, licking and sucking the head of his beautiful erection, when he leaned back to pull the drawer of the nightstand open to fetch some lubricant, and an anal plug. He generously applied lubricant to the end of the plug and then to his own ass. He handed me the plug and guided my hand to inserting it into him. His cock grew harder than I had ever seen it. I started pumping the plug in and out, while I took most of his engorged dick into my mouth. He came instantly, letting out a cry. I withdrew the plug while he lay there trying to recover. He was totally spent. I'd never seen him quite like that before.

It was a turning point for me. I was lying there, unsatisfied, and suddenly wishing he had done that to me.

A few days later, we were in bed again and much like before, while I was giving him head, he leaned back and produced the same two items. This time, before he could get the gel out of the tube, I spoke.

"May I please be allowed to experience that this time?"

Part of me couldn't believe my ears, and the other part was hoping he would accommodate.

Instead of lubricating the tip of the anal plug, Simon lubricated his finger. He pulled me up onto his chest and tipped me forward so I was on my hands and knees, dangling over his face. He began licking my pussy. He was so skilled at it. At the same time, he began massaging my anal opening. I was getting very close to coming. Just before I started what I call my final approach, Simon inserted his finger into my ass. It felt wonderful, and I spread my legs wider apart to indicate my delight. He added a second finger and continued probing until I shuddered in orgasm.

He repeated this many times over the next several weeks, alternating his fingers with the plug. I became increasingly more comfortable with it until I started actually leaving the lubricant out on top of the nightstand to speed things up. My orgasms were growing in intensity each time and I was becoming highly motivated to advance to the next step.

I felt like this man had been plenty patient with me, and now all I wanted to do was please him. I wanted to make the words I spoke a couple of months earlier be true -- I would do anything for this man. I wanted to give this gift to him. I wanted...

I received special instructions one morning in a note on the kitchen counter: Use the douche in the drawer this morning before work. Your outfit for tonight is on the sofa.

That was confusing. The first instruction clearly indicated that he intended for that night to be the night. The second indicated we were going out. I started thinking about eating a large dinner and what that might mean, and how much time that would take. I was doing it again...thinking through everything instead of just trusting him. I decided to let all the questions go, and just relax into the anticipation of the evening with an open mind.

Simon arrived early but I was already dressed and ready to go. I was particularly amorous and was acting a bit like a cat in heat toward him, rubbing myself against his chest and kissing his neck. He chuckled at my advances.

The exchange between us slowly began to change its tone as Simon unbuttoned my blouse. He slid the blouse down my arms and left it there so that it bound my limbs toward my back. I arched my back to proudly display my hard nipples. He ran his fingers across them and leaned down and took each one into his mouth. He then stood upright again and pressed down on my shoulders until I was kneeling. He started to make a motion to unbutton his pants but then stopped.

"I'll be right back. Don't move."

He went out the front door and I could hear his car door open and shut. He returned with a box. It looked like a jewelry box; the kind that might hold a watch or something like that. I watched intently as he placed it on the coffee table. I then returned my eyes to his, allowing my head to drop backward.

Simon then unfastened his pants and removed them, along with his underwear, socks and shoes. He stood there nude from the waist, down. His penis was immensely engorged with blood. It was red, hard and huge. I wondered how long he had been like that; how many times he had thought about our upcoming evening together. The day had been a blur to me. I could think of little else.

He leaned forward, allowing me to take his cock into my mouth. My lips slid down and up his shaft a few times, and then he stepped backward, withdrawing it from me entirely. Simon reached down and cupped his hand under my chin to raise me to my feet. He picked up his pants and carefully laid them on the nearby barstool. He then unbuttoned my cuffs and removed my blouse, shaking it out a bit and then hanging it on another barstool with much care. He did the same with his shirt and my skirt. His actions were very deliberate, as though he had planned each one with precision.

We were standing nude in the living room. Simon guided my arms around his neck and drew me closer, carefully positioning his erect penis upward between us. He gazed down at me, running his fingers through my hair, caressing my neck. I stroked his hair lovingly, paying close attention to every wavy curl as my fingers explored. I could feel it washing over me -- that incredible feeling of complete abandon. My body relaxed and my breathing became deeper. My lips instinctively parted and my head fell backward.

Simon's lips mouthed something but no sound followed. I thought he mouthed the word, beautiful. He started to breathe deeper as he kissed me passionately. His lips were pressed hard against mine, and his sense of urgency was so primal. He slowed himself down and kissed me gently and lovingly on my lips, cheeks, neck, ears, and forehead. He would do this for a few minutes and then change back into a frenzied, hard and forceful kiss. His excitement was fueling my arousal. Each time he probed my mouth with his tongue, I began grinding my hips and rubbing my body against his. My inner thighs had become soaking wet.

Simon finally stopped and took my hand in his. He led me into the bedroom. I stood next to the bed while he pulled the bedspread, blanket and sheets all the way down to the foot of the bed and laid one pillow at an angle at the corner of the bed. He patted the pillow, signaling me to lie down.

I lied on my back and he joined me, pressing his body against mine. The anticipation was incredible. Simon turned to me and whispered.

"Tell me what you're thinking and feeling right now."

I took a moment to think about it.

"I'm excited or nervous, I can't tell which. I'm wetter than I've ever been in my life."

With that, he slid his hand down between my legs. He smiled, withdrew his hand, and then looked at me, wanting more.