Şub 04

A Little Insurance

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“Yes, Bobby, I am sure.” The statement came from me in a hushed whisper that I had not intended to let slip so soon. His proximity to me assured he heard my confession although he continued watching me look over his house warming gifts.

In a time when we were both going through those troubling years of puberty, he was my sexual idol. Thoughts of sex with him consumed me; however, our families were well known in the community. I was not able to act on my desires then. Sadly, after high school we went separate ways and lost contact.

Years later, our paths crossed at a professional convention we attended. Our initial greeting was that of old friends reconnecting. We talked about life since school, our college years, and where we lived. We exchanged telephone numbers, addresses, and email accounts. We saw one another a couple more times at the convention although we did not have time to see each other more privately. His work group and mine had specific goals for the convention and he worked for a competitor.

We obeyed our promise to keep in touch. Through many telephone calls, email messages, and written letters, we poured out our histories after high school to each other. What we discovered was the sexual curiosity we both held for the other since our pubescent years of sexual discovery remained intact.

As luck would have it, we both planned trips to our old home town with overlapping dates. We planned to enjoy a few days together. Fate was not on my side as my vacation date approached. My boss, in name only, decided he needed me to cover operations while he conducted an “exploratory mission” in Nevada for a couple weeks.

“You will have to find someone else, ass hole! I fuckin’ quit!” I cleared my space, turned in my badges and keys, walked through the front door, and inhaled a breath of free air. I was more surprised by my action than anyone else in the office. It came out later that his “exploratory mission” was to the Bunny Ranch outside Las Vegas on his company credit card. “No, sorry, I won’t come back to fill the vacancy he left.”


“Yeah, I quit my job. My boss decided he needed to make a trip and leave me hanging. I am moving back home, going to buy a small house and changing my life style. I want to work at something I enjoy and not worry about pleasing some corporate ass hole. I’ll be there just as we planned.”

Our conversation ended on a happy note. My friend promised to help me get settled and was happy I took such a big risk.

Let me introduce myself and tell you a little about me. My name is Wilbur and I hate hearing the name; I go by Wil. I am single, in my late 40’s, and getting more rotund than I like. I am just over six feet tall and weigh just shy of 200 pounds.

Since college and my master’s degree, I have worked in the insurance industry. I never sold insurance; I was a watch dog making sure applications for insurance coverage met state insurance rules and laws.

I’ve had a couple relationships over the years but never married. Each relationship lacked something I couldn’t put a finger on. Maybe my change in life style will cause a new relationship.

My friend goes by Bobby and always has. At about my height, Bobby is more fit than I though beginning to show a little excess baggage, too. Bobby works in the insurance industry that I just left. Bobby spent years selling insurance before starting a climb the corporate ladder. Today, Bobby is a regional director overseeing multibillions of in force property insurance in the Northeast Corridor.

Before I forget, Bobby is not a female nickname. Bobby is Robert and he, like I, had relationships in the past but never married either. As I approach my move and spending a few days with Bobby, I wonder if we will complete the cycle of life to become sexually connected.


I bought a small house near my old neighborhood. It is a two-story two bedroom one and a half bath with a semifinished basement. It is older construction from the 1930s and has charm that modern construction lacks. My move in date came just as my planned vacation date came. With keys in hand, a car full of personal things, and a moving van parked on the street; I entered my new home.

Bobby was due home on his vacation in six days. I wanted to have everything comfortable when he did arrive, yet also knew there would still be boxes to unpack. Fortunately, I hired a paint crew days ago to paint the interior so walls, ceiling, and floors were clean and fresh.

A couple old friends came by and helped me move in. Beer and pizza still go a long way in this town and we got the heavy moving done in just a few hours. When calm after the storm settled, we talked into the night over more pizza and beer.

I filled the next couple days grocery shopping, getting window treatments up, and unpacking remaining boxes. “How the fuck does a single guy collect all this stuff,” I complained to myself. I made a couple boxes of donations to shelters, set aside some things for a yard sale, and the biggest güvenilir bahis boxes were full of junk to toss.

I didn’t have to deliver my donations as the local shelters pick up. One pick up was underway when some crazy idiot started banging at my door demanding I open up. The shelter workers showed their nervousness and my surprise didn’t help.

When I realized the voice was Bobby’s, I shouted back, “Fuck you! I’m busy, turn the nob if you want to come in!” I did drop what I was doing, went to the door where Bobby waited with his arms full of house warming gifts. Even before he could put his load down, I grabbed him in a warm embrace. “You’re a couple days early!”

“I had to get here before you got too settled. You need my artistic flare to make this place work.” Bobby took in the scene before him, “I’m surprised, you have this place looking good. I like your color palette. Are you developing your own flare now?”

The crew picking up donations left shortly after Bobby arrived and alone in the house, I embraced Bobby again. “Surprised that ole Wil has some flare, huh? Well, my style mentor helped me years ago and now he is back for more mentoring.”

“Well, Wil! Are you going to give me the grand tour? I like how you laid out the living room and dining room.” Bobby smiled broadly as we walked into the kitchen seeing it fully functional and ready to cook a special dinner.

“First, Bobby, let me introduce you to the refrigerator. Inside you’ll find wine and beer, a tray of cheese and cold cuts, and ingredients for a fine dinner that you will eat with me tonight.” I handed Bobby a beer making sure our hands touched as he took it from me. I know he sensed it as our fingers lingered longer than necessary. I took one for myself.

“Wil, I’m glad you moved back here and even more glad that we are no longer business competitors. What are you going to do for income?” There was concern in his voice and I felt charged up hearing it.

“I have many investments and built a very large nest egg. I am using interest as income now and won’t touch the principle for at least 25 years. The house is paid, mortgage free. I’m in good financial shape. I’ll do some freelancing just to stay active in the market.”

“I guess I was worried for you, Wil, but not any longer. Lets have the rest of the tour.”

I took a moment to look Bobby hard and directly in the eye, “Bobby, worry for me, I appreciate it and appreciate you for it. Follow me.”

We went to the basement to view the area of the house needing the most work. “This is my blank slate, not really sure what to do here.”

Bobby looked around taking mental pictures and notes, “This area is perfect for a man cave. I could go nuts fixing this up for you. We’ll talk about that more. What’s upstairs?”

I took the lead again showing Bobby the spare bedroom and full bath. Then I lead him into my master bedroom. It was the cleanest and most moved into room.

Bobby scanned this room noting furniture placement. There was a sunny nook where I placed a small reading table and a very comfortable antique man’s parlor chair. On the wall opposite the chair was a picture of Bobby and I from years back.

Bobby took notice of the picture. “Wil, you kept this old pic of us at the lake.”

“Yeah, it is something to remind me of our growing up years. I am fond of remembering that day, it was the last day we spent together before heading off to college and starting our adult lives.” There was more emotion in what I said than I meant for Bobby to hear; Bobby heard it clearly.

Stepping to my side, he struck the pose in the picture. I followed suit and for a brief moment, we were there again. “Could we ever be like that again, Wil?”

This time, I captured his emotion, put my arm on his shoulder, and took a risk. “We could if we wanted.”

“I guess you aren’t planning any over night guests since you have only one bed.” Bobby and I both picked up on the suggestive meaning of his statement.

“If it is the right guest, only one bed is necessary.” I held my gaze on Bobby.


We both felt the tension as we backed out of the master bedroom. Back on the main floor, we started some sorting. “These big boxes are full of trash to take to the dump. I planned on doing that this weekend. I’ve accumulated so much junk over the years, I needed this move to help me get rid of it.”

“Hey, Bobby, I haven’t looked at anything you brought in with you. What all is there?” I stopped picking through boxes and moved to the few things Bobby brought. Much of what he brought was memories from our youth. I latched onto a picture frame laying face down and turning it over, it was a copy of the picture in my bedroom.

Bobby watched me turn the picture over. I felt tears well in my eyes. With my voice cracking, I simple said again, “If it is the right guest, only one bed is necessary.”

“Are you sure, Wil?” My head bobbed up and down in an affirmative. “Yes, Bobby, I am sure.”

I knew, we knew, our türkçe bahis lives headed in a new direction. This new dimension of our lives quickly began overtaking us. I had no experiences of sex with a man though I knew I wanted the experience. Bobby told he thought about it as well but had never acted on it. Now we were both about to embark on a new experience.


I opened and examined the other house warming gifts although none were as important to me as the framed picture and the lusty thoughts that filled my mind. Bobby and I admitted in veiled words what we wanted. “Bobby, have you told your family you made it home a few days early?”

“Wil, no. No, I didn’t tell anyone. I came to see you first.”

I could not contain myself as I stepped toward him with the broadest smile my face ever felt. I took Bobby into an embrace meant for lovers and kissed his lips with passion. I’ve embraced many women this way, kissed them with passion, and enjoyed a night of hot sex. However, nothing prepared me for sparks igniting a burning flame. I hoped Bobby felt it.

Bobby returned the embrace and opened his mouth to mine and we began a tongue dual. My hands squeezed and massaged Bobby’s back as I let them slide lower until I squeezed and massaged Bobby’s butt. When I drew him tightly into me, I felt his cock rising to the occasion.

“Bobby,” I asked in a hushed voice, “what took us so long?” The taste of this appetizer made me want to enjoy the full meal. I did not stop rubbing Bobby’s butt or holding him close to me feeling his cock against my groin.

Bobby seemed to be somewhere else, a place that I hoped he could share. “Wil, I have never felt this charged. I knew coming home early to surprise you was a good thing. Thank you for proving me right.” Bobby brought his lips to mine and we kissed, hot, long, and wet.

“If it is the right guest, Bobby, one bed is enough.”


“Will,” Bobby spoke as he broke from our embrace, a happy smile on his lips, “if we don’t get back to this sorting and clean up, it won’t get done.” I nodded as I glanced at Bobby’s crotch. His cock was proudly pushing against the material of his pants wanting freedom; I was the same way.

We drank a couple beers and snacked on cheese and cold cuts while finishing sorting. There were heaps of trash piled on the porch for loading and hauling to the dump tomorrow. As afternoon waned into early evening, I invited Bobby to bring in his suit cases and stash them in my room. We showered, not together, and met in the kitchen where I began preparing our dinner.

We gravitated to each other as we worked together on the meal. At one point, Bobby reached around me for some seasonings, leaning close to me as he reached, I turned my head in time to give him a little kiss. We dissolved into another five minutes of kissing and hugging that stirred our cocks.

“God damn it, Wil! I am right on the edge of raping your ass! Fuck!”

“It would not be rape, Bobby.” I cupped the bulge in Bobby’s pants and it felt strangely good, long and thick. “I could take the edge off while the meat cooks.” It was my first directly sexual innuendo and I hoped Bobby was okay with it.

“No, Wil, I want the edge on. I feel like a horny prom date, I can’t wait and I don’t want to rush it.” Bobby sighed as I rubbed my palm along the bulge in his pants. I squeezed gently and felt his cock jerk from the sensation.

My cock strained for release and I felt my pulse pounding in my cock. I still hadn’t taken my palm from Bobby’s pants when I felt his hand massaging my bulge. “A very horny prom date indeed. I promise you this, Bobby, I surrender.”

We grilled steaks, baked potatoes, tossed a green salad, and drank wine with dinner. Buying beer and pizza doesn’t really count as dinner for guests who helped me move in and settle. Bobby was my first real dinner guest and I knew we would have a few more dinners before he had to begin his visit with his family. I hoped that also meant nights in my bedroom with little sleep.


There weren’t many dished to clean after dinner and we made quick work of the clean up. With our wine glasses recharged, we settled in the living room with music playing and lights dimmed. Side by side we sat talking about everything we could remember of our growing up years. We joked, teased, refilled our wine glasses, and were completely comfortable.

We touched, kissed, and acted like dates ready for the main event and not know who should make the first move. We were both virgins to gay sex although we were well down the road after an afternoon and evening of innuendos.

As if by mutual consent or mutual acknowledgement, we fell into a lovers kiss, hands exploring the other’s body. Buttons began opening and shirts falling to the floor. Skin to skin, it felt wonderful to embrace.

Within minutes, it was pant buckles and zippers slipping open, pants took their places with our shirts. Under shorts didn’t stand a chance of restraining or retaining our güvenilir bahis siteleri cocks. We stripped them off and were naked.

We were not speaking now, only our bodies and some hidden power propelled us. We took a big gulp of wine and went to floor kissing and groping. At one point we got into a 69 position. My hand stroked Bobby’s cock, his hand stroking mine. In a moment of true mental connection, we both began kissing and sucking cock. Bobby tasted wonderful and his clear oozing liquid added a unique aroma and flavor that I quickly became addicted to.

I was on the brink of cumming when Bobby began to squirm and moan loudly. His moans vibrated through my cock and my moans vibrated through his body. What Tesla and Edison knew about electricity was nothing compared to the charge of current flowing between us.

When it happened, it happened at the same time. Bobby ejected his first blast of cum and three more in rapid succession. My mouth became his dumping ground and I savored each taste. I did not swallow.

Bobby locked his lips around my cumming cock as his mouth tasted me. I have had blow jobs and had really fantastic cums from them; however, I had never felt as much cum leave my cock or felt the strong connection I felt with Bobby.

We did not stop sucking and finally had to swallow. It was a lovely feeling swallowing all of Bobby’s cum offering. He was still hard and throbbing in my mouth. His edge was not off and neither was mine. I was ready to offer Bobby my virgin ass hole.

I never considered whether I was a top or a bottom although I knew tonight I would take Bobby in me and feel him fucking me. When I found my voice again, I heard myself sighing almost begging, “Fuck me, Bobby.”

I had no clue what to expect other than I knew I wanted to feel him inside me. Bobby, shifted position as did I. How should I present myself, I pondered. Does Bobby want me in missionary, doggy, on my stomach? We spooned.

His cock wedged in the crack of my ass and felt warm, exciting. He slowly sawed against me creating good friction getting more demanding as he stroked. I did what I could to open more for him raising a leg and wrapping it over his thigh.

We adjusted more letting his cock make repeated contact with my ass hole. With each move, Bobby pressed into my ass. I was very relaxed from my first cum and excited to feel Bobby’s cock knocking at my back door.

On his next push, I pushed back and in an instant I impaled myself. I shuddered and moaned as the invasion continued. Bobby’s cock felt hot as it filled me and I pushed against each of his pushes. Bobby had one arm around my chest holding me. His breath on my neck made me swoon and his cock in my ass made me cry with pleasure.

“Wil,” Bobby whispered, “am I still the right guest to lay in your bed?”

The tone of his whisper was emotion filled and contagious. With equal emotion, I replied, “Tonight and any night you want. I felt little kisses on the back of neck sending signals I never experienced before. My anal muscles squeezed hard against Bobby’s cock and he gave me a cum reward.

I was more satisfied now than I have ever been after a sexual encounter. I felt Bobby’s cock in my ass, his cum coated my bowels, and still he was hard. His cum was like lube for my ass. Slowly, I rolled making Bobby roll with me. When I was flat on my stomach with Bobby on top of me, I told Bobby I wanted more.

“Will, are you happy I got here a couple early,” Bobby asked in a lusty voice as he began working his cock in my ass.

A smile spread across my face as I turned my head to glimpse Bobby face. I saw passion on his face and hoped he saw it on my face. “You are welcome to cum early and often. Kiss me Bobby, fuck me.”

Bobby already had two big orgasms making me believe this fuck would last a while. Bobby set a slow pace initially. He pushed deep into me and held himself deep for a few seconds before he withdrew slowly. Holding himself just barely in me, he began pushing in anew until I felt his whole being possessing me through his cock.

In time, Bobby picked up the pace sliding in me faster and harder. Something was going on in my ass. I felt pressure building in me like I had to grunt out the invader. When it hit me, I had no idea of such a thing as a prostate orgasm, but I was having one.

I heard someone yelling, “Don’t stop! Oh fuck, don’t stop. Oh, Bobby fuck! Fuck me.” It was me yelling like a girl. My cock shot off a load as my ass muscles contracted against the first and only cock ever to fuck my ass. Bobby blew another cum deep into me as we came together.

“Oh, Will, that takes the edge off,” Bobby sighed. I felt him relax on top of me with his cock finally giving up its hardness.

“Bobby,” I sighed with a meaning I had never spoken before, “I feel wonderful. Sex will never the same if it isn’t with you.” Bobby’s shrinking cock twitched in me when I said that and he pushed into me gently.

“It can be with me as long as you want, Wil. I have never been this satisfied after sex before.”

I felt Bobby’s cum oz from my ass when his cock slipped out and wedged along my butt crack. It was a post-orgasmic sensation I had never known and it felt sexy. I wondered if Bobby would let me fuck him.

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