Through the Ages

Jeff was recently out of the Navy. He served 20 years and that was enough. At 5'-11" and a fairly trim solid 205 lbs. He was in decent shape. 39 years old and recently burying his mother and grandmother in the last six months brought a new meaning to his future. These were the only females whom he bonded to through the good and bad times. Sure there were some "women" but nothing serious. He never really had any long lasting girlfriends, his own age. He looked older than he was. It was probably because of his rapidly, premature gray thinning hair. He worked out regularly at the gym. He loved to look at the women. You saw what a woman really looked like, sweating and could tell a lot by how they worked out. You could only hide so much in the gym.

At 5:00 pm one Saturday afternoon he was on the stair machine when he noticed two women enter the gym. The younger looking blond was about 5'-9" wearing loose gray sweats and baggy tee shirt, had a pale hue to her skin, decent chest and her hair up with a clip. Her partner was older, about 5'-4" tanned, brunette who obviously worked-out. She had a decent pair of tits, on the small and firm size. She wore a spandex blue-gray outfit. The bottoms came just below the knee and the top was short showing a firm mid-drift. He pegged them at about 28 and 36 years old. They got on adjoining treadmills and the younger one began talking incessantly about her life, in a rather loud manner. She virtually didn't let the brunette say a word. After eavesdropping on their conversation, they were obviously related, had to be sisters.

As time went on they switched to different machines together and proceeded through a thorough work out. Soon the blond was dragging and left to the locker room. As the brunette began working the arm machines she was having trouble adjusting the seat on one. So Jeff went over and offered a hand. A bold move on his part, he was almost never the one to start anything with women. After some small talk, she introduced herself as Dottie. Jeff hung close and continued the small talk. Dottie was more than willing to carry on talking, because she hadn't been talking for days.

"Since my daughter came two days ago I haven't had anyone that would listen to me" Dottie proclaimed. Jeff stared open mouthed and sputtered " Your Daughter? I thought that you two were sisters, damn Dottie you must have started young... real young, I'm shocked. "

"Oh Jeff, really that is such an old line, but very sweet. Surely you realize that I am a lot older than her. " Dottie said.

"No I figured you about mid 30's and "your daughter" about 25 or so. I'm sorry if I offended you, please forgive me for putting you on the spot. " Jeff said quietly. He got that familiar feeling that he really blew it with this one. How corny he must sound. Just another example of why he never related well to women his own age. Dottie realizing that he was shyly slipping away, felt he was worth pursuing called out the Jeff as he was turning to leave. "You didn't offend me, really, I am deeply complimented... Jeff, would you like to catch a drink after our workout? My daughter is going out tonight with some of her old friends and I am in no hurry to be alone this evening. " Being a manager of a real estate office, she was well experienced in handling people, especially shy people, getting them to open up. She dutifully looked down at the floor appearing somewhat embarrassed, hoping to get a positive response. It worked, Jeff on the spur of the moment snapped a resounding "Yes, Ma'am, I sure would. " Reverting to his military background.

As this concluded the blond "daughter" walked over to Dottie, introductions were made. Kayla was her name. She had been in the sauna and was quite sweaty. She obviously didn't take after her mom, she was a lot heavier and wasn't dressed for the occasion. She wore a black bra under the white tee, not really gear for the gym. She was somewhat sweaty; making the tee shirt was become a little transparent. Dottie was embarassed; it was hard to say if it was because Kayla's 38 Wide chest that dwarfed hers or that her daughter just plain looked dumpy, probably about 25 lbs overweight. After some small talk the three of them agreed that Kayla would drive home alone and Dottie would go with Jeff for a drink and then he would drop her home.

Things went well over at the local watering hole. Jeff found out that Dottie divorced her husband 8 years ago and was successful in business. About 3 years ago Kayla went to live with him in California, Dottie was too strict for her she said. Well then Kayla hooked up with the wrong crowd, got into drugs and who knows what else and was now returning home to get her head on straight. Kayla was only 19, but looked ten years older, she had some hard miles on her. Dottie was quite surprised herself to find out that Jeff was only 39. She pegged him at mid to late 40s. The hair threw her off. Now she was truly charged up, being 10 years his senior and he showing some true interest in her.

As she quickly downed a couple of margaritas, she became bold in her pursuit of Jeff. She began to touch his legs and arms while talking, and was discovering that this guy seemed truly sweet. After about an hour and a half of small talk and a couple of burgers, a lot of the men were leering at her, dressed as she was and she thought that it was time to leave. The evening crowd was arriving for a Saturday night of action. As they were driving home she wanted to take this further and coyly invited Jeff in for a spell in her hot tub. Kayla would be out, probably all night, and she didn't have anything planned. She played the roll of the lonely woman who needed some company. It took a few minutes but she talked Jeff into it.

Arriving home, Dottie ushered Jeff to the deck and the large hot tub. She went to get some more drinks. It was a spacious, nice home with a large deck and private backyard lined with trees and a privacy fence. "Well take your shirt off and get in!!" Dottie commanded, as she entered with a beer for Jeff and a wine cooler for herself. She then set the drinks down and boldly peeled off her spandex top, leaving a white sports bra. Although her tits were small, they really looked packaged nicely. She turned and undid her shoes and socks, giving Jeff an excellent view of her tightly packed ass. Then she stood up turned pulled down her spandex pants, leaving her in a thong. She loved the look on Jeff's face. She totally enjoyed this; she was the spider inviting the fly into her web. It wasn't often that she could get a younger piece, especially one that didn't come on too strong and was such a gentleman. She stepped slowly into the swirling water. "Come on Jeffy, bring the drinks and get in, it will soothe those muscles. " Said Dottie, with a big grin.

Jeff dropped his shirt and grabbed the drinks almost plunging into the water, hoping to hide his growing member, in reaction to the little strip show put on by Dottie. As he handed her the drink she sat down leaned back and took a long pull on it. Her bra was now wet and completely transparent. What gorgeous tits. Jeff wanted this moment to last forever. Dottie had an average looking face but had an outstanding tightly packed body for a woman her age. She drained the wine cooler after two more long drinks.

"Jeffy, be a dear and get me another of these out of the refrigerator. " Commanded Dottie. Being the good soldier, Jeff complied. Upon returning, Jeff's mouth fell agape, noticing that the bra and thong were now on a wet heap on the floor next to the hot tub. She noticed his reaction and innocently said "They got wet and weren't hiding much, hell we are adults, I just got a little more comfortable Jeff, I hope you don't mind?" She was playing him along right into her web of seduction now.

"No Ma'am, this is your house and you can surely do what you want. " Jeff said sheepishly, and looked to the floor, avoiding looking at her beautiful body, still minding his manners. He handed her the drink and followed with his eyes. Her breasts were perfect bite size. The years had been very kind to her. The breasts were very firm, and topped by nipples with small dark areola and firm tips. He thought that they looked like Hershey Candy Kisses. Instantly his prick responded. He knew he was larger than the ordinary guy. Every time he had a prostitute overseas, they all marveled at his thickness. He quickly sat down to hide it. Dottie reached over with her petite size 5 foot and brushed the outside of his gym shorts. Jeff began to blush. Dottie then stuck her foot up the leg hole and tried to stroke it with her toes. Jeff jumped at this and stood up in reaction.

That was Dottie's cue, she put down her drink, pushed off from the seat and stood on her knees in front of Jeff. "Why don't you join me, and take this thing off?" she muttered. And then she reached up and grabbed his shorts and jock and slowly pulled them down. Oh was she surprised! This may have been the thickest cock that she ever saw. It was a little longer than most, but damn this thing was wide. Jeff now did not protest. He knew what was happening. And he was going to enjoy it. After he stepped out of his shorts, they joined Dottie's abandoned clothes in a pile. Dottie placed her lips on the tip of his tool and kissed it, then flicked her tongue on the underside of the head a half dozen times. Jeff moaned deeply. She then inserted about an inch of the head in her mouth and sucked loudly.

Jeff thought that he was going to shoot his load. Sensing this, Dottie withdrew her mouth and stood up. She ordered Jeff to sit now. As he did that, he looked directly into a great looking pair of pussy lips, lightly highlighted by wisps of pubic hair. It was very neatly trimmed. Dottie pushed her pussy into his face. Now it was his turn and he didn't want to disappoint her. He stuck his tongue into the slit, and worked it on the top end. Gently working his teeth and nibbling the outer edges. Dottie was more than pleased. She wasn't sure he had eaten much pussy, but he was obviously experienced. She could stand it for only about a minute.

She withdrew and spun around, lowering herself on the fully erect dick, like she was sitting on a chair. It looked like a flesh colored cucumber. She wanted it in her badly. Her being small, him being big, this would take some time. They worked in unison. After a little patience, she had him in her. "OOOOOOHHHHHHHH!... MMMMMMMMMPPPPPPHHHHH. That is fantastic" she screamed. Her pussy was now contracting furiously. Jeff raised and lowered her in and increasing rhythm, she was light in his hands. Dottie couldn't believe what was happening. She was already cumming. It usually took several minutes at the least. "AAAAAAAHHHHHHHH!!!" That announced her pleasure and obvious orgasm. Jeff gently stopped the thrusting action with Dottie coming to rest in his lap, still hard inside her. He needed a little more action to relieve himself, but he didn't want to hurt her, there was time. Dottie collapsed backward on to his chest, leaned her head back and directed his face down for a sensual kiss.

Just then there was a loud noise from the inside of the house, followed by a door slamming. "Mom, are you here?" Kayla's voice pierced the night. "Damn kid! She wasn't supposed to be home yet. " Whispered Dottie. Dottie quickly dismounted and moved across the tub and sat down. She was quite flushed and somewhat dazed by the intense sex. Jeff was now stupefied. Naked in a hot tub with an approaching teenager. He was too far from the clothes pile to retrieve his shorts. Just wait it out, see what happens.

Kayla lumbered in, still wearing her workout clothes. "There you are. Oh, I hope I'm not interrupting, but my plans got changed, Becca's period came so she didn't want to go clubbing. I just stayed for dinner when I dropped by her house on the way home from the gym and I decided to come home early" Kayla was quickly surveying the scene and figured that her mother was trying to seduce Jeff. Kayla figured her mother was quite the prude and that maybe she would have some fun here. She continued " I see you two are comfortable, I think I'll join you. " Kayla said flatly.

With that she shed her tee shirt. Presenting that black bra, which it turns out was a lacy, seductive looking thing, not the kind you would wear to the gym. Kayla was very proud of her large breasts. She especially took joy in the fact that she was a giant compared to her mother, and she now was a formidable competitor to her. Kayla then reached behind and unclasped the structure, slowly slipping it from her shoulders. Her nipples were starting to protrude and her areolas were three times bigger than Dotties. She threw it on the clothes pile.

"Kayla! What are you doing, you just met Jeff... really, put your clothes back on. " Dottie shrieked. "Excuse me! But you look naked as a newborn, and you only just met him. I am an adult now, besides my legs are hurting from that workout that you put me through" Kayla replied while winking to Jeff. She then leaned forward, with her tits hanging down and looking even larger, and untied her shoes. Her nipples had light pink areolas the size of fifty cent pieces, and complimenting wide her nipples. After slipping out of them she untied the loose gray sweat pants and let gravity pull them down into a pile at her feet. Kayla was not wearing any underwear. She proudly showed off her completely shaved pussy, which was accentuated with a pierced labia gold ring. Kayla, was working her own seductive routing and really thought that she was hot stuff. Jeff saw her as an overgrown little kid with a lot of baby fat to lose. He wasn't particularly attracted to her, besides she was so young. She then stepped into the tub and sat closer to her mom so she could look directly at Jeff.

Dottie was now steamed. Her daughter was showing her up with those youthful gigantic jugs. Thank goodness she already some sex and had an orgasm. But she was looking forward to at least one more, until little miss slut showed. "Well, I am going to shower and clean up. " Announced Dottie as she stood up grabbed her underwear, tossed Jeff's shorts to his end of the tub and raced out of the room. "Jeff I forgot to take my socks off, would you take them off for me?" Kayla said in a playful voice. "Sure but I think that I should be going... Its getting late. " Replied Jeff as he grabbed the foot that was thrust at him. He gently, but firmly pulled one then the other off. Then he grabbed his shorts and was going to slide them on under the water. Seeing this, Kayla stood up and grabbed his shorts, catching Jeff off guard, and threw them across the deck. "Stay and play with me, won't you?" announced Kayla. And with that she stuck her right tit in Jeff's face.

Jeff was no fool. He took the tit in his mouth and started to flick it with his tongue maybe he could finish what he started with her mother. The entire areola was stiffening and the nipples responded in kind. He switched to the left one, same result. Kayla withdrew her chest and knelt down grabbing at his prick. She also was pleasantly surprised. "Do you have a license for this thing? A woman could get hurt on it. " Kayla teased. "Stand up and let me look this thing in the eye" She continued. Jeff rose slowly, feeling quite horny, as he didn't have a release with her mother; he felt very little guilt at playing around now, and he'd been with skankier looking whores.

"The boys on the West Coast said I was the best cocksucker in the county, let me show you" announced Kayla, and with that she worked his head into her pouty thick-lipped mouth. She slowly worked the head back and forth, adding about an eighth of an inch each time. Eventually she was deep-throating him. Jeff thought that she was right, she was a great cocksucker. Then all of a sudden he realized that there was something else dragging on the underside of his unit and heightening his pleasure. It wasn't teeth. Damn, it had to be a stud in her tongue. He was experiencing heights he didn't think were possible. He couldn't hold back. Sensing this Kayla pulled his tool out and roughly stroke it with both her hands and directed the stream toward her face.

What a fire hose. He should have cum with Dottie so he had quite a load built. Cum spewed out in thick wads. First on her hair and forehead. Then on her left eye. Then again on her hair and left ear. Finally one large wad landed just below her right eye. She gently kneaded the shaft milking the remaining large droplets onto her tongue. When the delivery was done, she let go and sat back on the hot tub seat, savoring the moment. She looked a mess, but this is what she wanted. Thick wads of sperm were all over her hair, and face, a face which had a smile from ear to ear. Jeff sat down, trying to hide his now flaccid unit. "What do you think of that? Pretty good huh?" Kayla said as she toyed with wads on her face, directing them to her mouth. She liked the taste and texture of sperm. She made long stringy displays of it with her fingers dabbing at it. Then she would lean her head back and drop them into her mouth.

Again there was some noise coming from the front of the house. The front door slammed. "Dottie, Kayla, where are you" a female voice called out. "Holy Shit! That's my grandma, I gotta get out of here. I can't let her see me this way" whispered Kayla as she jumped up and out of the tub in a youthful motion. Jeff was surprised that the big girl could move that quickly. She grabbed her shoes, pants, tee shirt and bra. She ran into the doorway off the side, where Dottie escaped just minutes ago. Jeff was experiencing another wide swing in emotions, from sexual ecstasy to the fear of being caught literally with his pants down. It was only ten-o clock and he had seen more action than in the last year. Now he was trapped naked in the hot tub, shorts across the room with a complete stranger, who was a senior citizen, approaching. He had just had sex with her daughter and grand daughter. Surely she wouldn't cause a scene call the police, would she?

Jeff was totally unprepared for this. A woman, who appeared in her sixties, dressed in a black dress with a silver pattern, which ended just below the knee. It accentuated her bust-line with a modestly cut vee neck. Her breasts were apparently larger than Kayla's. That's where she got it from, must have skipped a generation thought Jeff. Black modest two-inch heels and black hose. Puffy dyed blond hair attractively arranged. Classic case of "big hair" She wore smartly applied make-up with eyeliner and ruby red lips and gold jewelry.

There were some wrinkles, but they were well placed and gave her character. She was slightly overweight with a paunch in her stomach area, which was to be expected at that age. All in all she was probably the prettiest woman of the three in the family that he met. She heard the hot tub and wandered out to the deck.

"Oh, excuse me but I am looking for the girls, do you know where they are?" she asked looking around the deck, trying to figure out who he was and why he was here. There were wet footprints trailing out of the hot tub into the house, and she couldn't help but notice his shorts across the room. Jeff stumbled along introducing himself and blushing deeply trying to hide his nakedness and sexual conquests of the last few minutes.

"Well son, I was on my way home from an afternoon wedding of one of my dear friend's son and decided to stop by and see the girls, my name is Josephine, but everyone calls me Jo. " He countered with his name, but she just continued " It seems that I'm interrupting something, I'll just step into the house and check in. " She projected an air of classiness that the other two didn't have. As she moved, she began walking somewhat unsteady, Jeff was thinking that she might have had a little too much to drink at this wedding. She turned and followed the wet footprints into the house and disappeared. Jeff was in a quandary, should he get out and run for his shorts, risking getting caught? Or just wait until one of the ladies saved him, somehow. He decided to wait, he was embarrassed enough already. Sure enough less than a minute later Jo walked back out.