A Cautious Man

This story could also go in several other categories. If you're particularly worried about sex from some category that you object to, you can look at the tags at the end of the story. In the tags I have listed the other categories. I can tell you, however, that all of the sex is heterosexual.

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I'm basically an ordinary thirty three year old married Caucasian guy living in Middle America. I have average looks, average intelligence, average social skills, average athletic ability, and average height and weight. I went to an average High School and average college, I got average grades, and I have an average job making average money. Even my name is ordinary -- Bill Wilson.

I have only two real distinguishing personality traits.

My first distinct personality trait is that I am very cautious. I've never been a risk taker, not even in my teenage years when many people are wild. I make every effort to play the odds when it comes to health, investing, establishing interpersonal relationships, whatever. That's why I drink little, gamble even less, and don't smoke at all.

My second distinct personality trait is that I have a real aversion to drawing attention to myself. I don't like the spotlight; I'm a follower, not a leader, and am embarrassed if I garner too much scrutiny or recognition. There have been many times when I participated in group projects where I let the other members of the group take more kudos than I did just because I preferred anonymity.

I also have two distinguishing physical characteristics. My cock is about 30% longer than what I have been told is average, with a 50% larger diameter. Also, if properly stimulated, I can on occasion have three intense, full-discharge, orgasms in one six hour period. Maybe that's not much for fictional stories on sex sites, but is extraordinary for the real world.

The family that I grew up in was also pretty unremarkable -- that is except for my younger sister Tess. Tess has always been a real firecracker, with dramatically above average looks in every way. Actually, in my humble opinion she is about the best looking female I have ever seen live! She is the smartest individual in our family and the most energetic. She also is a great person.

Tess and I have always gotten along well, and had many school activities in common especially since she is only fourteen months younger than I am. We were much closer to each other than any other members of our family and always -- without exception -- supported one another. We were simply simpatico.

Tess and I could talk to each other about anything. We answered each other's questions about members of the opposite sex when we were teenagers, and even in our twenties shared our experiences and questions. We even shared a few fantasies, such as about threesomes and light bondage.

Tess understood my personality quirks and never chided me about how cautious I was, and interceded on my behalf if circumstances were making me the center of attention.

Virtually the entire time that we were growing up, Tess and I almost never went to sleep, or left the house, without giving each other a big hug and kiss on the cheek.

While I never had any trouble in talking with females and making female friends, due to my cautious nature I didn't date a great deal. That changed with an encounter with one of Tess's friends and classmates, Brittany.

In High School Brittany was more cute than beautiful, although her body was in the top 10% for females her age. Her personality was somewhat similar to mine in that she was also cautious, though with no apprehension about being the center of attention. She was always friendly and considerate, and I really liked her.

Brittany temporarily overcame her cautious nature before the Homecoming Dance of my senior year. She had just turned eighteen; I am seven months older than she is.

One Friday night Brittany was over at my family's house for a sleepover with Tess and two more of Tess' friends. As she was walking in the hallway on the second floor, apparently going from the bathroom to Tess' room where the other girls were playing music and chatting, she passed by my open door as I was reading Sports Illustrated.

"Hi, Bill. I'm surprised that you stayed in tonight with four noisy females disturbing your quiet," Brittany said with a big smile.

"Hi, Brittany. Actually," I chuckled, "it's great having four good-looking girls around instead of just one. Noise doesn't bother me and I don't have to worry about homework until Sunday afternoon."

"Yeah, every weekend I put it off until then too," she giggled.

We engaged in small talk for five minutes or so, and then the conversation changed.

"So, Bill, are you going to the Homecoming Dance?"

"Maybe," I replied, "if I can get a date. Are you going?"

"Well, I heard that two guys are planning on asking me..." she said then paused.

"Which ones, do I know them?" I inquired.

"I'm not supposed to say. But, anyway, I'm actually hoping that another guy I know will ask me first."

"Who?" I inquired, actually very curious.

"Well, I'll give you a hint. He is the brother of one of my good friends," she responded. When I apparently had a blank look on my face she continued. "He's a senior." Apparently I was still clueless. "He's in my trigonometry class." I guess I was still not registering anything. "I'm standing in his bedroom doorway right now," she finally said, with a hint of exasperation.

"Oh," was my profound reply; I'm sure that I turned red. When I didn't say anything more, Brittany got a look of between surly and dejected on her face and started to walk away as she said "Well, see you around."

"No wait, Brittany," I shouted after her. "Would you really go with me?"

"You'll have to throw caution to the wind, like I just did, and actually ask me," she said with her arms crossed.

I got up off my bed, walked to within a few feet of her and queried "Brittany, would you please do me the honor of going to Homecoming with me?"

"I'd love to," she replied, uncrossing her arms and smiling.

"Wonderful," I said with an equally big smile. "Can I call you next week about the details?"

"That would be great. Thanks, Bill. Mind if I tell Tess?"

"She'll sense it and beat it out of you anyway," I laughed, "so you might as well."

Brittany laughed, squeezed my hand, and then walked into Tess' room. Although the music was still playing loudly I could hear a few distinctive shrieks about a minute after Brittany walked back into Tess' room. That actually made me happy.

Things were a little awkward at breakfast the next morning, but I acted as naturally as I could toward Brittany and Tess. Despite Tess' normal protectiveness toward me, and help to avoid me becoming the center of attention, she engaged in subtle teasing, always with a big smile. It was clear that she approved of me going out with Brittany.

I made a point of saying goodbye to Brittany when she left, and reminded her that I'd call next week about plans.

To make a long story short, Brittany and I lost our virginities to each other three weekends after the Homecoming Dance. Being the cautious people that we were of course I used a condom. I only had one with me, however, and we both were up for a second round and therefore ended up slightly frustrated. Our first time was good, however -- actually really good for a first time. However, we both knew that it would get better.

It did get better. Brittany and I had sex virtually every weekend for the rest of the school year, and I never brought less than three condoms to each session. We made sure to use at least two of them each time, and often all three of them. We also experimented with oral sex, and found out that she liked sucking cock and I loved eating pussy.

Brittany and I also enjoyed each other's company when not having sex; there was the real possibility of a long term relationship. However, being the cautious people that we were, we dated others while we went to different colleges, but got together during the summers. By then Brittany was on the pill, so no more condoms with each other -- although we promised to use them with others to avoid STDs, and I always did. Without the condoms the sex moved from great to phenomenal.

It took me four and a half years to graduate, and Brittany three and a half, so we got out at the same time. We dated exclusively after we graduated college, and within a year we were married. Tess was the maid of honor, and Brittany's brother a groomsman.

By the time that Brittany and I were thirty we were able to afford a house, even though we had two young kids. By then Tess had gotten married too and had one youngster. To our joy, Tess and her husband Jack moved into a house only a block away from ours.

As part of our cautious approach to life, Brittany and I adopted some unusual procedures. One of the most uncommon was that we employed a portable "panic button." Our cellphones were modified so that by a simple surreptitious press of a single button Brittany could make both a silent 911 call and ring my cellphone with a distinctive tone.

Also, we kept a loaded shotgun at a convenient location in our house; being cautious we would never have a loaded handgun with two little children around given the statistics about the probability of an accidental discharge. However, our shotgun had been professionally modified so that it had a unique safety that only Brittany and I knew about -- one that was completely childproof but didn't require a key.

The neighborhood that Brittany, me, Tess, and Jack live in is a pleasant one. There are many mothers who are around Brittany and Tess' age and most are friendly, and a surprising number are hot. None are as hot as Tess, or even Brittany, both of whom have kept their fantastic figures even after kids; but close. One in particular is almost on the same level of hotness as Tess and Brittany; our next door neighbor, Gail. Gail has the biggest boobs for a slim woman possible -- I don't know how she walks without a back brace.

One Thursday night our kids were upstairs asleep, and I was working on my computer in just a pair of sweatpants and a T-shirt, while Brittany went to her twice monthly neighborhood book club at Tess' house. Usually five or six women showed up, all from the neighborhood. That night there were six, Tess, Brittany, Gail, Jen, Tammy and Bea.

After Brittany had been gone about forty five minutes the distinctive panic tone emanated from my cellphone. At first I didn't recognize it because Brittany had never used it before except in tests. However, after about five seconds I realized what it was, immediately pulled on a pair of slippers, grabbed the shotgun, and tore out the door.

As with almost everything else my courage is just average; however, an average person faced with my situation would be as aggressive as I was. Even though I was almost peeing my pants I was so afraid, that did not stop me from acting diligently and forcefully.

Running as fast as I could in slippers and carrying a shotgun, I got to Tess' house in about two-three minutes after the panic alarm went off. I barged in the side door, ran through the kitchen, and found three miscreants in the living room. One -- with a handgun in his waistband -- appeared to be almost through cuffing Brittany and three other women. When he saw me he drew his gun but I blasted him before he had a chance to shoot. My shotgun has a tight pattern and I'm decent at shooting skeet so I was quite sure that no pellets hit anything but his chest. He instantly went down in a heap.

As I got into the living room I could see Tess stripped of her clothes and one thug with his dick out about to rape her. He stood up as I entered and I blew him away with the other barrel of the shotgun.

The third guy was in the process of trying to rape Gail, our next door neighbor. He had quickly raised his handgun and fired, but it was off target. I charged him and hit him in the face with the barrel of the shotgun, knocking him backward, and causing his gun to go flying off to the side.

I tried to hit the third guy in the head with the stock of the gun, but he moved out of the way, and grabbed the gun barrel with one hand and my short sweat pants with the other. I fell on top of him and we fought furiously. He flipped me over, got on top of me and was starting to land a few very unpleasant blows to my head when I heard a loud bang and he crumpled off me to the left. After I pushed him completely off of me I saw Tess -- naked, with one of the criminals' smoking guns in her hand.

I quickly got up to see if everyone was all right. Despite my agitation, fear, angst, and whatever other emotion I was feeling, I remember thinking "Holy shit, Tess is hot!" but quickly purged my mind of that completely inappropriate thought.

I gently took the gun from Tess' hand, said "Thanks!" Tess was shaking. I turned to Gail, who was now on her feet, and told her "Call 911; the cops aren't here yet so maybe Brittany's panic alarm didn't get through."

Gail -- also naked -- hurried into the kitchen to make the call. If there had ever been any doubt in my mind if her gigantic tits were natural that doubt was dispelled as they freely bounced up and down as she scurried to make the call. I had to figuratively slap myself out of it to keep from staring at her, and to get back to seeing how everyone had fared.

As Gail was calling 911 I picked up a knife on the counter between the living room and kitchen and cut the plastic handcuffs off of Brittany, Jen, Tammy and Bea. Despite the confusion, punctuated by sobs, cries, and general bedlam, I noticed most of the women staring at me at one time or another with strange expressions on their faces.

Once everyone was sure that everyone else was all right and we heard police sirens in the distance Brittany came up to me, hugged me, and whispered in my ear "Your shorts were ripped in front during your fight with that asshole. You should cover up if you don't want to put on a show!" Despite the circumstances, the last comment was made with a chuckle.

I broke contact with Brittany, looked down at my crotch, and found that not only were my dick and balls poking out of a huge tear in the front of my shorts, but my long, girthy dick was at least three-quarters hard.

Embarrassed as hell, I ducked into the kitchen where only Gail could see me. She was still holding onto the phone with the 911 operator, but definitely took notice of my condition. I took my shorts off, and then turned them around and put them back on. I figured that it was better to have my ass providing the show instead of my cock. I then retrieved an afghan from another room and covered Gail with it so that she wouldn't be naked. Tess had put her torn, but still functional, clothes back on by that point.

Three squad cars screeched up to the house, about thirty seconds apart from each other, starting about a minute after I switched my shorts around. It was at least three hours before everyone got through being interviewed, the three hoodlums were carted off to the morgue, and things had settled down completely.

Not surprisingly, the police informed us that all three of the thugs had long criminal histories, including for sexual assaults. One was on parole, and another had skipped bail on a battery charge and was on the lamb. No tears were shed over their demise.

Shortly after the police arrived I had called my parents to go stay at our house in case the kids woke up, and Tess called Jack -- who was on a business trip -- to tell him what had happened. He called back a half hour later and said that he had canceled the rest of his meetings and was getting the first flight back the next morning.

The police collected the weapons and all of the outer clothing of the six women and me; Tess gave the women some of her loose fitting clothes, gave me a pair of Jack's gym shorts and a T-shirt, and with their motley clothes everyone left Tess' house. I was the last one to leave; I waited with Tess until our parents came from my house to hers once Brittany returned to my house.

As we waited for our parents, Tess put her head on my shoulder and quietly sobbed. As I comforted her I felt like a total shit because my dick was still saluting since I was unable to get the image of her standing naked with the smoking gun out of my pea brain. The only reprieve I had from that image was one of Gail's big natural honkers -- and that certainly didn't help deflate my little friend.

As you would expect, the next several days were really hectic. Our town had not experienced much crime in the past, and essentially never a home invasion. The press was all over the place. While some of the women, Gail in particular, seemed to relish the spotlight, this was my worst nightmare. Attention was being drawn to me. Between neighbors and victims coming over to my house to profusely thank me and applaud Brittany and me for our panic button system, and the ever-present press, I was experiencing more angst than I ever had before in my life.

After about a week the furor finally calmed down. Jack, me, and two of the other husbands of the victims had repaired all of the damage to Tess and Jack's house except for three art objects. To garner public goodwill within a few days after the incident Tess' and Jack's home insurance company even gave them the full value of the destroyed art objects without applying the deductible. Tess was more than happy to tell the press about their generosity, and even posed for a photo with the insurance agent handing her a check on page one of the Metro section of the local newspaper.

I never gave an interview to any member of the press, and the only images of me that appeared on TV, the Internet, or newspapers were candid ones taken from a distance. There were many people who were confused about why I didn't want to accept public hero worship, but they didn't have my personality quirk that made the praise almost as difficult for me as the incident itself had.

One thing that I didn't mind, however, was the genuine enhanced friendliness of the victims, Gail, Tammy, Jennifer and Bea. My relationship with Brittany didn't need any strengthening, but she was even more attentive than usual and would do anything to please me sexually. Tess was a problem, though.

I could not purge my brain of the shame that I felt for how I was now looking at Tess. While I still loved her with all my heart as a sister, no matter how I tried to deny it I had developed sexual feelings toward her. What made it even harder was that she was even more physically demonstrative with me than she had been before the event. Whenever we were together she never missed an opportunity to hug me tightly, or gently touch my arm.

Our town's mayor wanted to give me an award at a ceremony, which I flatly refused. He even tried to get Brittany and Tess to persuade me to go along with it, but they knew me very well and made it clear that I would never attend a public event where I was to be honored.

The neighbors also tried to throw a party in my honor. To my surprise Tess did attempt to get me to agree to a party, rather than indulging my personality quirk like she had the rest of our lives. However, I was able to weasel out of the party too, although I got a little uneasy when I finally declined the party that Gail pushed her big boobs into me and with an evil grin said "You'll be sorry!"

About five weeks after the incident Brittany brought up a "Thank you" that I really couldn't refuse.

"Bill, the neighbors have gotten together and want to pay for a long weekend trip for the two of us to a fancy resort in the mountains. There will be no public clamor," Brittany told me when I got home from work one Thursday evening.

I started to say "I don't know..." when she cut me off.