The Chronicles of Monica

In order to lay an adequate foundation for Monica's story, it is necessary to detail the part that someone named Gwen played in this scenario. I contacted Gwen through a singles' dating site. After the initial contact, we scheduled a date and I went to meet her. We had a pleasant evening together dining and talking and later returned to her home for the balance of the evening.

We sat and enjoyed a movie, but she complained about her shoulders being sore from work, so I invited her over to massage her back and shoulders. At first, she was on the floor, but later raised up to sit between my legs on the couch. As I continued my ministrations on her back, she became more receptive to my touch and I became more daring in my moves as she moaned her approval. I am certain that she felt my growing cock on her backside. Ultimately, she released her bra and I continued. As we needed more space, she suggested that we relocate to her bedroom where we be more comfortable. We both disrobed and I continued her massage. As could be expected, she lay on her back and I proceeded to fuck her in her bed. I must confess that she had the tightest pussy I had ever entered up to that time including my first wife's virgin pussy years ago.

The point of all these details was her comment that I was exceptionally good at the massage that I administered to her back and shoulders. It got me to thinking that if I could be that good not knowing what I was doing, how much more effective could I be with instructions. The next day, I contacted a local massage therapy school to inquire and found myself enrolled as a nighttime student in an upcoming session beginning in a few weeks.

After the episode with Gwen, I started school and became reacquainted with Monica. On the first day of class at massage therapy school, when I entered the school office, I found Monica sitting on the reception desk and to my surprise also engaged in the same study, albeit, she was in the class ahead of me and finishing up her studies making up some classes she has missed because of sickness.

I had originally known her during her innocent years as a high school student where my own children had attended. After graduation and moving out on her own, she rebelled against the rules at home and ventured out into the world to find her own way in the restaurant and hospitality fields. During this phase as I am led to understand, she exhibited a rather rebellious and free-spirited nature, was conditioned to staying up until the wee hours of the morning and was inclined to experiment in the realm of sexual relationships. I think it goes without saying that she desired to experience unknown things she had only heard about but not seen in action or in person. I think she even embarked on a journey into swinging and a degree of promiscuity as once she commented on the size of a man's cock we encountered while shopping. Apparently, he was huge. I do not know whether she knew that from her own personal experience with him, or whether she had merely seen in naked at a party. She never elaborated.

After she settled down somewhat, had a child out of wedlock and married a couple of times, we stumbled across one another years later; we came together in a relationship which at one point I thought might move forward as I was acquainted with her whole family from years earlier. Nevertheless, the relationship ultimately failed but that is another story. We had begun our relationship on the heels of yet another of my failed relationships. As things deteriorated in that relationship, I sought counseling to determine who might be crazy, her or me. Nevertheless, Monica was with me to comfort and help me recover from some surgery and we spent about a year together. During that time to allow me to experience things I had never experienced, she suggested that we pursue some avenues of adventure to expand my own sexual history which at that point was pretty bland and unexciting.

Among other things that I determined during my relationship with Monica was that we were both co-dependent upon one another, that is dependent upon the other for our own individual happiness. That fact determined our respective responses to one another's actions during our time together and led to some arguments and discussions. Some of her history and future actions made me extremely jealous.

One night, however, while we were out dining, she convinced me to head downtown as she wanted to show me something. Once we parked in the entertainment district, we walked down the sidewalk and to my surprise, we ended up in front of a tattoo parlor. Upon entering the establishment and looking around, negotiations were concluded, and we headed to the back of the establishment were Monica climbed on a table, spread her legs, and the artist commenced piercing her labial lip with a jewelry ring. I watched as he pierced her skin. She stifled a groan as he quickly completed his task with precision.

In a later period of self-discovery and sexploration, we took a cruise wherein she hoped to set me up with one or more female passengers on the cruise. While in Key West we missed Fantasy Fest because of timing, but we visited the clothing optional bar on Duval Street, called Adam and Eve, I think, and she had the opportunity of showing off her newly acquired piercing in the bar to visiting patrons.

We met a couple there who also seemed to be into sexual and relational experimentation as well, but when they suggested we accompany them to their house I balked as they were totally unknown to us, we would have to be too far away from the ship, and there was no guarantee that they would bring us back to the ship in time before it set sail. Additionally, I had no idea what might be in store for us if we succumbed to the offer and temptation. Monica being bisexual was quite turned on by the woman, but the woman seemed to be fearful of interacting with me and there was no guarantee that there would be a place for me in this equation. It seemed as if I would only be a spectator to whatever might do down. It angered Monica that I did not feel compelled to participate in what might have been planned for us. It later prompted some additional discussion, yea argument, regarding swinging protocol and involvement.

While the cruise did not generate any additional partners as we both hoped, other things were tried like a nude hot tub experience and coed skinny dipping at a school related party. That party ended up with two drunk naked guys swinging their dicks and having a brawl. During my experience in the swimming pool before the fight, a beautiful young lady whom I held in my arms reached down to cup my cock, but apparently I was not big enough or hard enough to satisfy her curiosity so she got out of the pool and returned to her lounge chair and nothing further developed although I had hoped it would.

After venturing into the realm of public nudity, upon our return from the cruise, I arranged for us to have an overnight stay at a nude resort nearby. After we arrived, the park manager, an older gentleman, took us on a tour of the facility in his golf cart clothed in only a towel. After retreating to our room, we headed to the pool sans wardrobe and towels. We jumped into the pool and enjoyed ourselves. Sexual activity is basically forbidden in public at most family-oriented nudist resorts that are not swinger adult-oriented facilities, but we managed to discreetly fool around a little bit in the pool. Monica stroked my cock, and I fingered her pussy. After retiring from the pool, we returned to our cabin and fucked our brains out because of the excitement level we achieved. While we were in the pool, another young couple arrived to preview the resort. I watched from afar as they disrobed next to their car, placed their clothes on the seat and joined the manager on the golf cart as she escorted them around the park. I was quite amused as the man exhibited a healthy hard-on sticking straight up in the air as they drove by. His wife was a real pretty woman and, I got a real nice closeup look at her pussy as she squatted down near the edge of the pool.

Monica was into anal sex, so I had my first entry into the hidden chamber. Even after that experience, anal sex never did much for me either to deliver or receive.

On the matter of swinging and other partners, during our time together, Monica used my newly acquired laptop for school to access some internet sites and contacted several individuals. One couple consisted of a man and woman who lived in the next state and who were both bisexual and who invited us to join them. He encouraged me to try sucking his cock as he offered to suck mine. While I turned down his offer, nevertheless, he put me in touch with another swinging group elsewhere in the state who were more receptive to my visits later as a single male partner after the relationship with Monica hit the skids.

If there was one characteristic or quality about Monica that I appreciated the most during our time together, it was her affinity for cleanliness or hygiene. I do not like smelling or tasting shit amid a sexual encounter. With even the remotest chance of partaking in any form of sex, she would immediately take a shower so that every one of her openings were pristine clean. From time to time as she showered, I would rush to the kitchen and grab up some eating utensils and prepare a place setting on the bed with a pillow between the utensils. When she emerged from her shower, I would coax her into lying down so that her ass was on the pillow and I prepared to eat her pussy. She loved having me eat her pussy and I delighted in eating her. Her pussy was one of the best I ever tasted. She had many orgasms this way. I absolutely loved her pussy. I am not certain any other woman could compare with it in my eyes. Monica was into going commando and rarely wore panties. From a health standpoint, this lessened the likelihood of a yeast infection which can occur with too little ventilation in the vaginal sanctuary and with fabrics other than cotton.

Since Monica and I were both in massage therapy school together, it was only logical that occasionally we would get together with other students to both socialize and practice our new found skills. We would often practice on each other and it would typically devolve into a sensual massage ending in sex. Brenda was a friend who was also studying to become a massage therapist. She came to the house one day to visit after work and before the evening was over, we applied our blossoming skills to one another.

I was first to crawl up on the massage table. Even with Monica's sexual history, I was reluctant to interact sexually with one of Monica's long-time friends, so I settled for retaining my underwear. Both girls worked on me and made me feel extraordinarily nice. Unfortunately, with my uncertainty about how to act toward Brenda in Monica's presence, there was nothing sexual about the massage I received.

However, when it came time for Brenda's massage, she stripped down completely and lay on the massage table on her front. Monica and I set about to massage her. As we continued, the massage took a decidedly sensual turn. Following Monica's lead, our hands began to explore every part of Brenda's amazing body. Brenda had been quite big girl at one point and had successfully managed to drop a sizeable amount of weight so much so that she could be described as petite. In addition to the weight loss, she had also had her breasts augmented and they proudly stood up on her chest.

Again, following Monica's lead, I began to massage her butt and casually slipped my hand and fingers down between her legs. The longer she remained in position, the wetter she got.

After completing her back side, she flipped over and unashamedly gave us a show of her front torso. While Monica worked on her neck and shoulders, I proceeded to work on everything else. I got to wrap my hands and fingers around those marvelous tits and concentrate on her magnificent nipples as she began to moan.

I worked my way down to her legs and spent much time on her mound using the heel of my hand to apply a sensual pressure to her sex. She moaned even more and spread her legs to provide me with greater access. I concentrated on her labia with occasional passes over her clit. She got wetter by the minute and her groans and moans intensified.

Brenda was married so I was not quite sure how she felt about certain things and what I could do but, I settled for a finger fuck. I would really have liked to have moved her down the table and fuck her but did not want to chance irrevocable damage to my relationship with Monica in overstepping unseen boundaries, nor cause conflict between Monica and Brenda.

On another occasion, Monica made contact with some woman on an internet swinging site. She invited the woman to the house for a massage. The woman was quite attractive, but as they wound their way down the hall, I was not invited to watch or participate. I did manage, however, to get a glimpse of the woman naked through the crack in the door as she dressed to return home. I repeat again, that Monica swung both ways, so I am certain that there was a degree of love making behind the closed doors during the massage.

One weekend while in a particularly adventurous mood, since Monica's sister and her family were out of town, we went down to their house, slipped through the gate, stripped down and went skinny dipping in their pool. Since I had never fucked in a swimming pool before, I bent Monica over the hand rail and proceeded to fuck her brains out in the night air. After we concluded our activities, we slipped back out the gate, unnoticed by the neighbors, and headed home.