Allan and His Mom Pt. 02

The moment seemed ripe and ready for a special question I had been saving up to ask mom, about Will of course.

Mom's Tail's Tales

As we sat on the porch hammock waiting for the power to return, I decided to bring up one sensitive subject: "Mom, was Will the first man in your life?"

"In certain way yes, I knew Will for long time since my older brother and Will became close friends when they were at the Engineering School. He is two years older than your uncle and 10 years my senior. So when they started doing their homework together in our place I was ten years old. Throughout the time they became inseparable friends, Will was from a faraway city and a poor family. Your grandma liked him very much so he used to have lunches with us almost all Sundays and diner several times a week. So I grew up seeing Will as some sort of older brother. I was sixteen when he graduated at college and start working."

"At the time I was a very complicated teenager. I felt my butt was too big, my thighs too thick and my tits too small. On top of it all, I hated my hair that was too curly in my opinion. As you can imagine I was pretty unhappy with my look. Then I started noticing Will's subtle interest in me. In the beginning it sounded like an old friend doing his best to comfort an ugly duckling. Once we were just the two of us talking and I said I didn't feel at ease wearing jeans. He wanted to know why and after some resistance I told him why: I believed my ass was too large and it would look bizarre in tight jeans. He said that I was crazy, that there was nothing wrong with my rear and made a complimentary commend about my body."

"I felt like in heavens and begun to figure that maybe I was wrong. Of course my body never would win a beauty contest, but even so it was much better than what it was in my self-evaluation. Right after I turned eighteen, it became more evident of Will's growing romantic interest in me. He had just bought his first car and one Saturday he stopped by my home looking for my brother (later on he admitted he knew my brother wasn't there. He used it as an excuse to see me). He invited me for a ride and I fondly accepted. We rode throughout the city and at a certain moment he stopped at a promenade with a dominant view of the city. This was one of the favorite places for young people enjoy good times with their sweethearts."

"We talked for a while a when he pulled a pack of cigarettes from his pocket I quickly grabbed it saying he had smoked enough for that day. He begged for the cigarettes saying he would die without one and tried to take it from my hand. Then somehow, all of a sudden, we were exchanging a passionate kiss. The next step was to open my blouse and loosen a tit from the bra. I never have had such a caress and of course I was feeling heavenly. It is hard to believe but until that age I haven't had a boyfriend, all my sexual experiences were my masturbation sessions during the bath or at night in my bed."

"I pleasurably accepted the fondling in my breasts and a bold hand roaming up my thighs. I only decided to stop him when he attempted to insert a finger in my pussy. I was virgin and educated by my mother to only give up my maidenhood to my husband at the honeymoon. He smartly changed the focus of his attentions moving the hand to my ass, even so over the panties."

"From that day on we started dating but in a very strange way. It was clear Will knew that my parents didn't see favorably our relationship. I'm sure the problem wasn't the age difference but the fact that Will was almost mulatto and my parents were very proud of their ancestry. The truth of matter was we hide our relationship from everybody but my brother. In the presence of my parents we act like good friends, Will was, for all purposes, considered some sort of old brother after all. Even my brother, Will's best friend, didn't seem to see our relationship in a positive way. Even so, as a support to his friend and his beloved younger sister, he even gave us the much needed coverage."

"Now, looking to the facts from a distant perspective I'm sure I was never in love with Will. He had shown up at precisely the right moment to support a needy teenager. Time passed and our petting sessions became bolder and every day I turned more eager for his caresses. However, since the beginning, I made clear that I was virgin and had intention to remain so up to marriage so my pussy was some sort of 'forbidden territory'. In the beginning he made some attempts to sneak in my furry triangle but always found my strongest objection. Disregarding this we use every moment to exchange caresses."

"Will was some sort of sales engineer spending most of the time out of the office and used to pick me up at the school almost every day and he drove to a secluded place where we gave expression to our lust. One weekend my parents traveled to a nearby city to attend the twenty-fifth wedding anniversary of some friends. As usual Will and I have had an enthralling petting session and when he drove me back home he ask me if we could stay together a little more. I wasn't sure since there was nobody at home and my parents would be very upset if they found that Will and I were alone at home."

"Anyway I couldn't cope with his pleads. Soon I was sitting on his lap and after opening my blouse and unclasping my bra he played for a long time with my tits. I was in such a state of arousal that I didn't oppose when managed to remove my panties and eventually play with my soaked pussy. Most surely I wouldn't make any attempt to stop him of breaking my sherry but he didn't appear to have such intention. Without a word he forced to kneel in front of the sofa and bend over the seat. He raised my skirt exposing my naked bottom and caressed it for a long time, massaging the globes and sliding the hand down the crack till reaching my back entrance."

"Immediately I understood what his intention was; I had heard from schoolmates about anal sex. Some said it was okay and very much enjoyed it; others said they tried and was extremely painful. As I said I wasn't in condition to refuse anything and I made no objections when, after spiting in his hand, I felt the knob touching my anus. With a resolute thrust forward I felt my sphincters stretching and something invading my then virgin ass."

"It wasn't by any means painful but as much as he shoved his penis in my entrails I was taken by a sensation of discomfort. Something as if I had a hard turd stranded in my rectum and wasn't able to expel it. But as soon as he begun to pump his pecker back and forth in my rectum the discomfort was subtly changing in an intense pleasure. He was extremely excited due to all our previous petting so it didn't take a long time to Will unload his semen in my entrails. Even so it was enough to cause the strongest orgasm I ever had in my life."

"For almost a whole year we had several sessions of anal sex, each time to my growing satisfaction. Of course we introduced several other options but for me the "piece de resistance" was always to feel his semen being spurted in my entrails."

"After this period Will got a job with a government contractor to work in the construction of a mega-dam in the western region, several thousand miles from where we lived. At this time he began to send me letters. At the beginning he wrote about the loneliness and the boring life in a place faraway form everything. After that his letters became more and more sexual with detailed descriptions of the things he would like to make with me next time he was in town and to avoid problems I rented a post office box. I was very excited with each letter reading them hundreds of times."

"He used to come to town every sixty days for meetings at the company headquarters. And every time he was in town we used to do some of the things he described in the letters. In the beginning the letter arrived at an average of two per week but as time was passing they became scarcer. At my side I was getting tired of that situation: I used to live in perpetual state of arousal and with little gratification: after experience a man's tool inside my body the masturbatory sessions weren't enough to satiate my sexual compulsion."

"Eventually, my brother came to me and said he had something to tell: Will was seriously dating a secretary at the dam and had plans to marry her. Certainly for any woman the news would be a disaster or a tragedy but I received the notice with relief. It may sound odd but I never perceived the relationship with Will as a stage of something that would grow to another level. In other words I never saw us married or in permanent relationship."

"It was also at about the same time when I had an opportunity to get my sweet revenge against a cousin. This woman, some years older than my mother, was the 'family pain-in-the-ass', the kind of person that spends her life finding a way to nag people. She was the one that nicknamed Mom 'Rumpy' a malevolent reference to Mom's slightly larger than normal posterior. Talking about her a little, it is ironical what the passing times can do to a person: she was once a tall very seductive woman but after a difficult pregnancy, before turning thirty years, she looked a wreck."

"The poor woman probably had added around fifty pounds in less than seven years. Needless to say her husband left her to marry with another woman. This was a time when she was pregnant with her first son and doing very badly: After one interrupted pregnancy her physician had told her to stay in bed after the sixth month. Even so she was doing poorly and one weekend my Mother asked me to stop by her house and drop a gift off which she had bought for her niece. That particular day she was doing particularly bad and asked me to stay a little with her, while her husband went out for some shopping. I sat on her bed and we talked for sometime but soon she fell asleep as result of the medication she was taking."

"I sat back in the living room reading while waiting for her husband to come back. The guy arrived and invited me to stay for a coffee. We went both to the kitchen to brew the coffee and sat back in the living room. Under the excuse of not disturb his wife's rest he closed the bedroom door. We sat face to face and sip the coffee eat some cookies. It was when I noticed his stealth stares at my body. I had my legs crossed and certainly he was having an eye-catching view of my thigh partially covered by the stocking. Too bad that now days those sexy glimpses are gone with women's preference for pantyhose. It was when he started complaining about the problems they were facing."

"According to him my cousin was obsessed with the idea of having a child and after she lost the first one, she got pregnant again shortly after, against her physician advice and without completing the hormones therapy he had prescribed. When we finish I went to the kitchen to wash the cups, he stay leaned in the door threshold looking fixedly on me. I finished the chore and picked-up my purse to go, but at the door he asked when he could see me again."

"I will be back soon." Was my answer pretending innocence.

"No, I want to see you alone, far from here!"

"I believe your wife wouldn't like it very much if she came to know..."

"If neither of us tells, she never would know. What do you think?"

"I don't know. This was so sudden." Picking up on my responsiveness to his suggestions, he hugged me by the waist and we kissed. I reciprocated by opening my mouth and French kissing him. His next step was to raise my skirt and try to touch my pussy."

"You can do that; I'm virgin." Was my answer breaking the kiss. The disappointment was visible in face and before he had recovered from the surprise I added. "If you want, we can do from behind." He virtually dragged me to a second room he used as a home office. He leaned me over a desk, raised my skirt, lowered the panties and without foreplay he inserted his prick in my anal aperture. While he was pumping in my rectum I began to think about the irony. Here I was there, just few steps away, serving with my rump the husband of a person that once pejoratively called me 'Rumpy'. After finishing our crazy sodomy session I hurried back to home."

Loose Ends and a Tight Ass

While she had told her story I was playing quietly with my hands over her body. She was wearing another dress shirt that was some sort of Mom's "summer uniform", she always had several of them with slight variations on the basic structure: all front buttoned, sleeveless and knee high. I started unbuttoning from the top and soon she was sitting there with her breasts exposed since she wasn't wearing bra.

I lean over her chest and took one nipple in my mouth. Mom had fallen silent and the only sounds around were the raindrops falling on the roof. Without Mom's opposition to my actions I followed unbuttoning until the dress front was fully opened. A hand was swiftly slid underneath her panties and when I touched her cunt it was drowned in Mom's juices showing how excited she was just by remembering the story.

In spite of the darkness we were outside home and there was only a three feet high wooden fence separating the house from the street, besides which the small bushes weren't enough to hide us from an occasional passerby. In any case, it was a rainy night in a deserted area so the chances of someone seeing us were minimal. Once again Mom didn't objected when I removed her panties leaving her practically naked. My next movement was to open the fly and free my hard prick. I took hold one of Mom's hands and placed it over my pecker. She grabbed it gently squeezing the shaft. It was the first time Mom touched my penis.

"You never kissed it; why?"

"I don't know... would you like that?" Without waiting for my answer she leaned back her torso; I felt her lips gently touching the glands and she gave a little peck on the tip. She then began to gently poke my glands with the tip of her tongue. She did it for an endless time, I was beginning to believe that, such as my Dutch young friend, she wasn't enthusiastic about having a man's flesh pole inside her mouth. It was when she placed the lips in the tip of the knob and forcing the head down gradually opened them inserting my pole in her mouth. I would say she had half of my seven inches in her mouth when she eventually stopped.

Soon afterward she raised and lowered her head, shoving the pole as deep as she could take and withdrawing till she had only the knob inside her mouth. Conversely from my initial belief my mother had thoroughly mastered the art of oral sex! Combining her expertise with my high degree of excitement it didn't take too much time to me to feel that was in the verge of another powerful ejaculation. Feeling it Mom aimed the glands to the mouth of her roof so avoiding me to spill my jism in her throat and making her retch. Eagerly she drank my sap to the last spurt not wasting even a drop. When she had finished with her job Mom still remained for some time playing and sucking my flaccid maleness. When she raised the torso I kissed her in the mouth. I still could smell in her breath the unmistakable odor of sperm.

We decided that was better to bed since the lights weren't on and they believed the Electricity Company only would fix it after the storm was over. Naked in the bed Mom cuddle me and begun to rub her pussy against my thigh. It was when I realized how selfish I had been. Once satisfied I didn't take care in pleasing Mom!

"Why don't you help him in get hard again?" I whispered. Mom was ready and eager to have my semi-flaccid inside her mouth again. It wasn't necessary a great effort from Mom to turn my tool rock hard again. She slithered over my body and holding my dick with one hand directed it to her pussy and lowered the body, inserting my dick with a sole stroke of her body. I decided to reward all the oral pleasure I received from Mom so it was a long fuck, Mom moaned crazily with our groins grinding each other till I couldn't control my libido anymore and filled her womb with my hot cream. During that extended session she had orgasmed several times and then, both spent, we slept in each other's arms.

"Mom, what is the story of those photos?" I asked when we were at the beach one day, some days later. "After your father and I came to an agreement about the future of our relationship, I started dating other men. When Will was back in town, as usual he paid a visit to my parents. We had dinner together and I noticed Will's renewed interest in me. Of course he was smart enough to conceal it from my family, showing his feelings just to me, but only when my parents or my brother weren't paying attention. The flirting was increasing and in a certain moment I felt his barefoot lightly rubbing my leg underneath the table.

Problem was my brother had volunteered to take Will back to the hotel. When we were leaving he gave me the usual kiss in the cheek and whispered: "Call me at the hotel!" After getting back home and I called him. We talked for a long time and we set an encounter for the next day at the hotel. Well, we spent the whole afternoon having sex, this time not only oral and anal such as in the old times, but also vaginally as well. From that moment on we use to see each other about once a month when he was in town for meetings at his company headquarters.

He always liked photography and once he proposed to take some naked pictures. In the beginning I refused; I was afraid that during the development process someone would make copies, but he assured that he would do everything at the company's lab. The photographer was his friend and would give him access to the lab. When we started I only agreed to take photos not showing my face but after some time I stop being so cautious about that."

"How long did it last, I mean the photo sessions?"

"Around two years."

"Do you still meet him?"

"No, it ended up at the same time as we stop with the photo sessions."

"And why?"

"It just ended like many other relationships. On my side it was okay to meet him once a month, he was an excellent lover. The problems began when he came with odd ideas about some other kinds of photos and I didn't like them..."

"What do you mean by odd ideas?"

"First he suggested we may include another woman in the photo sessions, he was obsessed with lesbian stuff. After that he said that a friend of his and the girlfriend would like to meet us for sex sessions including photos. In the beginning I believed that it was just some sort of man's dream but his insistence was growing every time we met. I'm not against anything in sex; it is a matter of like or not. If you like it is okay, but in this case he was forcing a situation on me and besides would be very risky for me to involve others."

"After all I was a woman, married and living in the city. The last thing I want was a sex scandal, one thing is cheating your husband and the other one is being involved in this kind of kinky stuff. Eventually I decided to voice clearly my opposition; he was a little pissed but never mentioned it again. But it seemed that he was trying to make all his sexual fantasies true with me. In another occasion he ordered a bottle of wine and we drank it all. You know, I'm not used to drink so I was a little tipsy. In a moment he decided to take a picture of the bottle inserted... you know... there... in my pussy. I rejected it, we had a strong argument that ended up with me dressing up and running away."

"It was when I came to conclusion that our relationship was coming to a dangerous part of the tricky path. But there was an issue: the negatives. I insisted only to see him once again if he gave me the negatives. After some reluctance he did it. We met for a couple of times and finally the relation ended. At the time he had divorced from his wife and was deeply in love with another woman."