First The Son Then The Mother

I'm Bill, a 52-year-old guy whose wife died from cancer a few years back and I haven't matched up with another female since. I live in a great condo in the Adirondack Mountains of New York State.

My phone rang one Saturday morning and it was a woman living with her son in a unit a few doors down from mine. After going thru the normal pleasantries she asked if I would do her a huge favor. Her 18-year-old son, Jim, was in his senior year in high school and if he didn't do something to get his math grades up the teacher told her he would flunk and have to repeat the year. The kid had been held back once before in one of the earlier grades and if this kept up he would be drawing Social Security before he got out of high school. She knew I was in engineering and figured I must know something about the subject and was hoping she could persuade me to tutor the lad. I agreed to give I a try.

Jim came over that afternoon and was kind of embarrassed to be needing the help. He was a tall lanky kid who really need to get some meat on his bones. I did my best to put him at ease and after spending some time on the basics realized he was going to need some help on the fundamentals if we were going to make any progress at all. Three nights a week for the next month were spent going over the part of the math book with which he was having trouble and it looked as if we were making some progress. He came over one night beaming and threw a paper in my face showing he had received an eighty six on that day's test. He was as proud as he could be and deservedly so; it was the first passing grade he had ever received in the subject.

I decided that night I would give him a break from all of the cramming I was forcing him to do and we just sat there shooting the breeze. We hit about every subject I thought a fellow his age would be interested in from sports to music and then on to some of the pop stars on TV and movies. Somehow the subject got around to sex and I found he had never been on a date and couldn't help but ask in amazement that here he was eighteen and had never had a piece of ass. He blushed and admitted that was true. He sheepishly mumbled that he might like a guy better than a gal. Oh boy, a young virgin and my cock was getting hard just thinking of his sweet young mouth and ass.

"Jim, do you jack off a lot?" I asked.

"About every other day. Is that a lot?"

"Nah, not really. Have you ever jacked another guy off?"

"No, but I watched some guys do it to each other in a car one afternoon."

"Jim, I have some porn DVD's showing some guys in action. Would you care to see them."

"Oh yes. I'd love to. I only have read a few magazines on it and the pics weren't that good," he replied.

We were sitting on the sofa in my living room and I started the discs and his eyes were soon glued to the set. I tried to act as disinterested as I could but I was keeping an eye on him to see if he was getting aroused watching the action. He was soon drooling over what he was seeing. All I could hear was his heavy breathing and a lot of oohs and ahs as the guys on the screen hit various positions. The bulge in his pants was starting to show and he was leaning so far forward towards the TV I thought he would fall face down on the floor. Maybe it was time to introduce him to some local cock ...mine.

I unzipped and took out my half hard cock and his eyes really opened up. My cock is a solid eight inches but not quite as thick as those on the disc or the ones shown all over the Internet. Without saying a word I reached over behind his head and pulled him down to where his face was only a few inches away from the head of it.

"Jim, you looked as if you were really interested in the guy on the disc doing this to his partner. How about trying it out on me?"

"Gee, I never did anything like that before."

"No problem I'll guide you through it."

I kept up the pressure on the back of his head and he soon had his lips brushing the head of my cock. More pressure and his mouth opened and he took me in about an inch or so.

"That's great Jim. Keep going," as I kept up the pressure. "Jim, why don't you kneel on the floor between my legs and it will make it easier for you?"

He slid down without losing anything he had gained on my cock.

"Jim, go down on me as far as you can and it will really make me feel good."

He soon had about four inches in and I told him to start bobbing the way he had seen the guy do on the disc. That was all he had to hear and he was bobbing as if he had been doing it all of his life. I was raising my ass off the sofa and holding my cock up to meet him and was soon fucking his face.

It didn't take long before I had the warm feeling start deep inside of me and was faced with the question of would I come in his mouth or let it fly outside for the first time for the kid. He could hear me breathing harder and must have realized I was close and he started to go much faster. That answered it ... he was going to get the full load in his virgin mouth.

I unloaded a huge stream and he gulped it down as if he was thirsty for it. By the time I finished giving him the load I was soft but he kept his mouth around it.

"Lick all of it from me Jim. I hate to see you waste a drop."

"Bill, I really enjoyed doing that to you. Does that make me gay?"

"Jim, what's 'gay'. It's just a word. If it turns out you would much rather have sex with a guy than a gal then we can discuss the terminology. Until then just leave it that you like to please me. OK?"

"OK" he answered but he still had his mouth just barely touching the head of my now completely soft cock.

"Jim, there's some more action on the disc I want you see. That guy who was sucking his partner off is now taking his cock up his ass. I'll be wanting to do that with you as well some time."

He sat up and all he could say was, "Wow, that looks as if it might hurt."

"You can rest assured when I do it to you I'll be very tender and lubricate both of us up. You'll be fine when we do it."

****

We went on with the math lessons for the next several weeks with Jim giving me a blow job about every other time we were together. The guy was getting very good at it.

During one visit I suggested:

"Hey Jim, why don't you strip down and jack yourself off while watching the pic on the TV. I'll bet you will shoot your wad quickly."

"Nah, I don't think so." He replied.

"Jim, I just phrased that as a suggestion. Now I am telling you. Drop your pants and get busy jerking your cock off." I said with a totally different tone in my voice.

"OK Bill, if that's what you want me to do." He responded with a soft sheepish small voice.

His cock was rock hard when he let all four inches of it out. That was his problem ... he was embarrassed at the small size of his dick.

"Now start jacking tiger. I want to see the juices fly from you."

He leaned back against the front of the sofa and grabbed his cock between his thumb and first two fingers and was beating himself so hard I thought he might damage himself. He was looking down at his cock and every now and then would look up at the action on the TV and that would have him beat even faster.

"Bill, I'm going to shoot soon."

I threw a small towel down to him and sure enough he was shooting a solid stream at least seven or eight inches in the air. What he missed on the length of his cock he made up for on the size and power of his orgasm.

"Whew, that felt great. I think I was over-aroused from doing that to you and then watching the guys on the disc in action."

"No matter, as long as you feel good. Now look what has happened" and I pointed to my hard cock. I had gotten aroused just watching him jack off.

"Jim leave your pants there on the floor and come with me. It's about time we tried another way for you to please me." As I led him back to my bedroom.

"Lay on your side on the bed and I'm going to lie behind you with my cock between your legs. I am going to act as if I'm fucking your ass without it going in you at all. My cock will just be between the cheeks of your rear and up against the lips of your ass and then down to your balls and I'll move the same as I would with it in you."

It must have excited him for he almost leaped on the bed and had the tight little cheeks of his ass staring at me. I lay behind him and positioned my cock to slip between his legs and started the motion.

"Jim, that feels nice. I can feel you throwing yourself back at me. You must like it too."

"It does feel warm and tender." He answered.

I rolled him over on his stomach and rolled right with him so I was on top of him and driving my cock harder between his legs. I was pumping fast and furious when I heard him say, "Bill, would you like to put it inside of my ass the way the guy did on the flick?"

"Oh yes big boy. Are you ready for that?" I asked.

"I'd like to try it and please you. Will you try and not hurt me too much?"

"Jim I'll use plenty of lube on my cock and your ass and we'll go slow and easy. I think the secret is for you to relax and not get your ass all tensed up. I did this to another fellow some time back and he got to love it once he learned to relax."

I got a jar of Vaseline from the bathroom and smeared a huge gob of all over my cock and when I got back to the bed took another gob of it on my fingers and slid one up his ass. He moaned a bit but moved his ass around as if I was already in him and he was reacting to me fucking him. I replaced my one finger with two and slipped them in slow and deep and moved them in and out in a normal fucking motion and then let them slip out and put three fingers together teepee fashion and did the same again. This time he was moaning as if he was in some pain.

"Jim, how is that feeling. I want to loosen you up a little before I slide my cock in you?"

"It started to hurt a little but the pain went away when you moved your hand."

"Great, lie on your side and I'll go in that way."

He rolled over and I had him throw his ass back to me. The lips of his puckered red asshole were now inches away from the purple head of my cock. I leaned forward and soon had an inch in him. He gasped and I could feel him throwing himself back at me.

"Are you OK Jim?" I asked.

"God it hurts a lot. Please don't go in any further."

"OK Jim. I'll stop right where I am for a little while. If you relax more it won't hurt so much."

I reached down and put a hand on his hips and pulled him back to me as I kept up the pressure. I soon had five inches buried and pressed forward even more. My cock sort of has an upward turn to it when it is hard and I was getting the feeling the head of it was massaging his prostate and that what was giving him some extra pleasure.

"Oh Bill, please no further."

I stayed right where I was but started a slow but steady thrusting in and out and could hear him moaning with a combination of pleasure and pain continued to feel him pushing his sweet little ass back at me.

"Oh God Bill, I am going to shoot a load without ever touching myself. It hurts terribly but you really have got me hot." He purred.

"Jim, the walls of your ass are gripping my cock tighter than even your hand could. It feels unbelievable."

"Wow, here it comes." He yelped and I could feel him throwing his ass back at me harder than before and saw his hand drop to his crotch to help himself along.

I then held his hips even tighter and pulled him back to me harder as I drove my eight inches in to the base as he screamed bloody murder. I was fucking him as hard as I had ever fucked any woman and it didn't take long before I was filling his ass with stream after stream of my white-hot juices.

We lay there for a few minutes without moving before I gave another few thrusts with my softening cock.

"Oh God, Bill. That hurt really bad but I was glad we did it for you."

"Glad you enjoyed it Jim for I sure did. Why don't you change the sheets on the bed while I put some coffee on? We can then shower and get cleaned up"

****

Our math lessons went on for another few weeks as we were approaching the end of the school year. He came knocking on my door one night and was all out of breath as I answered it.

"Bill, look," as he handed me his math final exam paper ... an eighty- three.

"Great Jim. You made it. You are going to graduate after all."

"Bill, I couldn't have done it without your teaching. You were wonderful. I don't know what I can ever do to pay you back"

"Well Jim, I haven't had a good piece of ass in some time now. How about hopping onto my bed and letting me open your ass up a little?"

"Oh yes. If that's what will make you happy." As he slid past me and went back to my bedroom.

"Jim, strip down and get up on your hands and knees. I'm going to have you up on your hands and knees 'doggie style'."

I grabbed the usual jar of Vaseline and smeared a gob on my cock and a ton on his ass and got up on the bed behind him. This was going to be pure fucking ... no foreplay.

My cock was positioned right in line with the tight little opening and I pressed the head of it against him. He instantly pushed back at me and I slipped all the way into the hilt. He gasped a little but kept up his rearward pressure. I had a hand on each of his hips pulling him back to me and then I started some plain old hard fucking. I did the usual of ramming my cock in and pulling it out almost all the way before driving it back in to the hilt again. It didn't take long before I was filling his anal canal with gobs of my white-hot come.

"Oh Bill, I can feel you shooting up inside of me ... don't stop."

"I won't Jim boy" as I kept unloading stream after stream up his tender young ass.

We showered afterwards and sat around talking sports and my cock got hard all over again. "Jim. I am not going to fuck your ass again but you can do your thing with your mouth on me this time."

He dropped to his knees in front of me and almost took my entire cock in his mouth before pulling back to take a breath.

"Oh yes Jim. Do it that way and I'll be exploding in a minute."

Sure enough he kept up the deep throat routine and I filled his mouth with come in a very short time.

"Well Jim Boy. I guess we are finished. I was glad to be of help to you with your math and equally glad you were able to give my long neglected cock some relief. We'll have to get together from time to time. What do you say?"

"Oh yes Bill. Anytime you want."

Jim was able to get a job in the nearby McDonalds for the summer as he had applied and had been accepted in the State College a hundred miles downstate. I wasn't going to see much of him anymore since we didn't have any reason to get together.

****

A week after the boy graduated his Mom came knocking on my door again and when I opened it there she was holding out a bottle of Scotch to me.

"Jim heard you say this was your drink and I wanted to thank you somehow for all you did for him." (Little did she know all I did for Jim)

"Oh hell, you didn't have to do that." I said as I took the bottle from her and ushered her into my place.

"By the way my name is Sally and I am tickled to death Jim was able to graduate. He never would have made it without your help. He and his classmates are away on a long celebration weekend. They sure worked hard enough for it."

Sally is to be kind, fat. She is pretty enough but she has to tip the scales in the one-seventies. Again, pretty, but fat.

"I was glad to be of service." (Great word for opening up her son's ass with my cock.) "How about me cracking this beautiful jug open and joining me in a little taste?"

"Wonderful. Scotch is my favorite as well. Just make it neat on a few cubes."

"One neat scotch coming up Sally."

We sat around talking for an hour or so but before she left I had invited her to dinner the next night.

The restaurant was a half-hour drive from our condos but well worth it. It is a cozy log cabin type of structure with terrific food. Dinner went great and we laughed and joked during the entire meal. She turned out to be a fun person to be with. I learned her husband had been killed in a car accident some years earlier and she had a pretty decent job as a financial consultant.

We walked out of the restaurant hand-in-hand as if we were a couple in love. Our car was parked near the back of the parking area and when we got to it just sat there for another while still laughing and joking about a myriad of things. There came a time when there was complete silence in the car and she turned to me and asked,

"Bill, do you think it possible you would ever consider having sex with someone who looks like me? I know you are a good looking hunk and I am a fatso but I'm really not a slob."

Her question had me stammering and stuttering for the next minute or so. "Sally, why do you put yourself down so?"

"Well, it's true. I can see myself in the mirror and can see I am fatter than hell. I have been on a diet and exercise program for the last two months and have lost fifteen pounds so far but I still have a long-long way to go to get down to my target weight. I let myself go after my husband died and never got back in shape."

I finally reached over and held her hand. Her response wasn't like anything I would have expected or was prepared for. She slid a hand up behind my head and pulled us together hard and let her tongue begin searching out mine. I slid a hand down to her chest and let my fingers cup a breast. That had her squirming and groaning as I let my fingers massage it through the top of her dress concentrating on what I could feel was a rock hard nipple. The kissing got really hot and heavy and I finally took her hand and dropped it on my lap. She knew exactly what to do. Her fingers were soon busy lightly massaging my cock through my pants. Whew, the woman is fast.

I slid my own hand down to my crotch and undid my zipper letting my cock spring out to her hand. That was all it took. She started jerking it while her tongue was still busy in my mouth. I wanted a lot more than a hand job from her and put a hand behind her head and pulled her down to my lap. She didn't need any more encouragement than that and soon had her mouth wrapped around my rock hard cock and had it buried a solid five inches or so. Holy shit, I was soon touching the very back of her throat with it without any effort on my part. Talk about deep throat ... she wrote the book. It didn't take much of that before I was filling her hot little mouth with my juices. She licked me dry before sitting back up and letting her head fall back against the head- rest of the car seat.

"Wow, Sally, that was terrific but now it's my turn. How about going back to my place so we'll have more room?"

"Mmmm, sounds good to me," she answered softly.

By the time we got back to my place my cock was starting to react to what it knew was just ahead ... a warm wet pussy.

We weren't in my place more than a couple of minutes before she was stripping her clothes off on her way to my bed. I was right behind her and my cock was like a flagpole pointing the way. Her breasts weren't large by any stretch of the imagination but they had beautiful nipples. I lay beside her with my mouth on hers and my fingers gently uncovering her clit. She was moaning as she squirmed under my touch. It wasn't long before she was tossing her head from side to side with her hair flailing out behind her head and she was throwing her hips high in the air.

She soon had her hands clamped on to the back of my head pulling it deeper into the folds of her pussy lips. I could not only feel her arousal begin but I could hear her breathing and moaning getting faster and louder. She let out a low sort of howl as her orgasm overtook her and she was crushing her pussy against my face as she was exploding. I thought she might enjoy a little more so I raised up from her crotch and positioned my cock in front of her pussy and slid it in. She was soaked and I went to the hilt in one easy motion. If she was moaning before the sounds she was now making were unbelievable. She was gasping and moaning and throwing her pussy high to meet my thrusts