A Surprise Affair

The story does not contain sexual activity involving people under 18 years old.

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Since my husband, John, died about 8 months ago, the 2 most important people in my life were my son, Ross, and my BFF, Penny, whom I knew for almost 23 years, since our college years. The sudden death of John caught us unexpectedly; he seemed healthy and never complained about pains or difficulties in performing tasks. He even exercised routinely. We didn't ask for an autopsy, so the reason for the death was not verified. Financially, we were lucky John made sure his life insurance was generous, and with my salary as a CPA it was more than enough to afford us comfortable living.

Ross was now 19 and was a sophomore at UCLA. I was very proud of him. He was 6'2", 190 pounds, very manly with light brown hair. It was interesting that he was great on the football field, yet very shy outside the field. On multiple occasions I attempted to talk to him about his feelings, but he managed to avoid discussing those. I often wondered if he would have been able to pour his heart to his father if he was still alive...

Since starting college, he once briefly told me he went out with a blonde girl named Wendy, but after that one time mentioning her, I have never seen or heard about her again. I remember talking about it with Penny. She chuckled, "Jenny, let me find out."

Here is the place to tell you about Penny. Like me, she was now 42 years old. At 5'4", 130 pounds, brown wavy hair, cute face, and a curvy body, she attracted attention wherever she went. I guess the way she dressed had something to do with it too: Her bosom was always prominent, and ample cleavage was the norm. Her dresses and skirts were on the short side as well, displaying her shapely legs. Each time we went to public places, men would ogle her voluptuous, partly exposed figure, and on multiple occasions, tried to date her. During the many years I've known her, Penny dated many guys, but each one for very short time. Her explanation was that her choice of men was awful, thus she preferred to use and then dump them. She claimed she only loved me. I smiled and thanked her for the compliment but was surprised she didn't use her attraction to better handle, if not her emotional needs, at least her physical ones. She winked and said, "One day, when we both are in the mood, I'll tell you more." I didn't push.

...

On the 1 year memorial of my husband, Ross had an exam and could not attend. After visiting the grave, Penny accompanied me home. I was crying my heart out, feeling the void after John's passing and remembering the good times we've had together. Penny attempted to console me, but I continued weeping nonstop. Then she went to our bar, pulled 2 bottles of alcohol and a jar of ice cream, and said, "Honey, let's have a feast and get drunk and forget all our troubles." In the following 40 minutes, we recalled happy moments with John and us two growing up. In college they used to call us Jenny-Penny, cause we were inseparable.

After about an hour, both of us got really drunk. We danced in the living room, listening to Oldies music. Penny hugged my tummy from behind and led me on the floor. Once I wobbled, and her palms grabbed my tits. I giggled, "Honey, that feels good. Nobody touched my boobs in exactly a year."

Penny kneaded my tits lightly and chuckled, "Darling, I always admired your breasts. Remember we went to buy underwear together? You said you were jealous of my larger boobs, and I answered yours were perkier and sexier. I really meant it."

"But why, every man would rather touch yours than mine?"

Penny's fingers massaged my mammaries as she whispered in my ear, "Silly girl, I fell in love with you years ago. I love not only your tits, but your hands, legs, tummy, and everything else." Next, she stopped dancing, gently turned me around, and mumbled, "In college, I didn't tell you about my love because I was scared you didn't think it was appropriate and would leave me. Later, you married John, so my only option was to be your BFF. Now I love you more than ever before..."

She stared into my eyes lovingly. I gazed at her, and for a moment, neither of us moved. Then she cupped my cheeks and kissed my lips tenderly. At that moment I loved her too. Was it because I was overcome by losing John? Was it the alcohol? Or was it my true feelings? I was too confused to think. I returned her kiss, and soon we were hugging and French kissing.

The next thing I realized, I was being guided to my bedroom by Penny. She slowly undressed me, unclasping one button at a time. My eyes were hypnotized by her fingers as my blouse was pulled off my shoulders. Not long after, my skirt landed on the rug as well. I was standing before my BFF in my underwear, not sure what to do. Penny unfastened my bra straps, and lightly rubbed my exposed C-cup breasts. Her warm delicate touch was pleasant and erotic. I moaned and hugged her neck. She gazed lovingly into my eyes and murmured, "Love, I waited too long for this moment. I want you so much..."

I whispered, "Penny, I also love you."

She knelt before me, lowered my low cut panties, and stared at my landing strip, "Your cunt is perfect. Just like I imagined it to be."

She buried her face down there, sniffed it, and I felt her tongue licking my moist folds. I spread my legs, letting her into me, feeling immense pleasure. Her tiny tongue swirled rapidly, now and then penetrating the hole, making me hornier by the moment. I pulled her face deeper into me, and within seconds came with a whimper. She continued munching on my labia for a couple of minutes and then slowed down. She stood up, and I saw her face stained with my juices. I kissed her lips. Penny was somewhat shorter than me, with brown wavy hair, pretty face, and D-cup tits that, despite her age, stood firmly high on her chest.

She undressed. When she finished, I bent onto her large boobs and gingerly sucked on her dark nipple. She groaned and muttered, "Jenny, let's get on the bed. It will be more comfortable."

She lay me on my back and mounted on my body. Penny kissed me passionately as her hands tweaked my nipples, increasing my arousal again. Next, her pelvis started grinding against mine. My wetness grew fast, but it wasn't fair; I orgasmed already while Penny hadn't. I turned her upside down, and changed direction 180 degrees until I was on top in a 69 position. I parted my thighs over her face and savored her musky-floral odor. Subsequently, I lapped and milked her nectar before licking her labia circularly, ensuring her love button remained untouched. Her groans were music to my ears and increased my horniness further. I inserted 2 fingers into her tight pussy and massaged the anterior wall. Shortly after, her tummy tensed, and she began shivering wildly. I continued kneading her G spot, and then I let my tongue rough her clitoris. Her body jolted in the air as her hands squeezed my tits, and she screamed, "Oh my god, it's so much better than I thought..."

Hearing Penny screaming and feeling my boobs being savagely manhandled, my own orgasm was not far behind, and I came violently, squirting onto her face without the possibility of stopping the constant stream. Gradually, I regained my strength and rolled onto her side. We stayed like that for a few minutes, and then I raised my upper body and looked at my lover. She opened her eyes and grinned at me.

I mumbled, "Sorry I squirted, but you aroused me too much..."

She smiled, "No need to feel guilty. I enjoyed everything. I wasn't ready for the sudden flow, but when I recovered, I tasted it, and it wasn't bad at all. Honey, I said it before, and I'll say it again. I love you dearly."

I chuckled, "I wonder how I would have behaved had I known about your love earlier. Would I have gotten frightened? Gotten cold feet? Cave in?... I do not know the answer, but I am happy we at last know how we really feel about each other."

Penny hugged me and whispered, "I love to touch your beautiful body and kiss you. I'd love to sleep the night with you too..."

I laughed, "We can try it, but not on weekends when Ross is around."

That was the beginning of our intimate relationship. For the next 6 months, after work hours, we ate, showered, went out, had sex, and slept in the same bed every night. Our relationship flourished even though neither of us felt we were lesbians. Circumstances led us into the current situation, and whether somebody would call it being bisexual, we didn't care.

...

In time, both Penny and I started eating healthier and exercising together. Our bodies looked more toned, and we were more cheerful. One weekend, Ross arrived home and watched me smiling broadly. He commented, "Mom, it's nice to see you recovered from Dad's death. These days you look gorgeous. Truly a MILF!"

I chuckled, "Thank you, son. By the way, how is YOUR love life lately? The way YOU look now, no girl can resist you. Why don't you bring your current girlfriend, so I can meet her?"

He blushed, "I went out with a classmate until a month ago, but we separated."

I hugged him, "I am sorry to hear it. But I am sure you'll find a new one soon. It reminds me; Penny will be here in 15 minutes, and she is dying to meet you after months she hadn't seen your face."

Penny entered the front door as her usual lately: Without knocking and underdressed. She had on a summer blouse without a bra underneath, and her giant melons swayed noticeably as she strolled toward us. The miniskirt was too short as well. Ross gave her one look, and his face turned ruby red.

Penny ignored his facial expression, moved toward him, hugged his broad chest tightly, and blurted, "Hey, handsome, we missed you around here. The man of the house was MIA for too long. You've become a real stud there in college. What do they feed you? Spinach?"

Poor Ross tried to free himself from her body, and the moment he succeeded, the reason was clear: There was a big bulge in his pants. I smiled and said to Penny, "Girl, leave him be. Don't you see what your big boobs do to him?"

Penny lowered her gaze to his groin and giggled, "Honey, that is the best compliment you can give to an oldie like me. I also find you extremely attractive."

His face reddened further, and he just stood there, not knowing what to do.

I attempted to save him and said, "Ross, please put water in the kettle so I can prepare the drinks."

As he moved to the kitchen, I told Penny to stop harassing him. He was too shy to confront her overt sense of humor. She smiled innocently at me and mumbled, "I just wish to be in his good graces, because I need a favor from him. The fence in my yard was damaged by stray animals in the neighborhood. I called several landscapers, but they said it was too small a job and not worth their time."

"Penny, I have no doubt he will be happy to help you."

The rest of the afternoon went without a hitch, and Penny behaved perfectly. Before she left, she asked Ross if he could come to her house on Sunday morning to fix the fence. He grinned and promised to be there at 9 am the next day.

The following morning, Ross drove to Penny's, and I went to the health club. I returned around noon, and Ross wasn't home. I showered and later began working in the kitchen on the following week's meals. Ross arrived home sweaty and declared he was going to shower. I continued peeling the potatoes and preparing the meat when he came out. He wore his shorts without a top. I stared at him, feeling proud of my creation. My son was really a hunk! Penny wasn't exaggerating when she called him a stud. His muscular, hairy chest reminded me of his late father, and tears started running down my face.

He saw my face and came closer, "What is it, Mom?"

"Oh, nothing. I just watched you and remembered your Dad... Your body looks very much like his..."

He put his arms gently around my waist and murmured, "Mommy, I love you, and I'll always be here for you."

I smiled through my tears, "My knight and shining armor."

After lunch, we chatted about his classes and future plans and watched TV together. He was still having on only his shorts. I could smell his manly, fresh odor. I thought to myself, 'My man is growing up so fast. Pretty soon he'll leave the nest.'

Later in the evening, he kissed my forehead and disappeared into his room. I read a book and then went to sleep. Around midnight, I had a bizarre dream: I was lying in bed, having my usual skimpy nightie on and reading, while I noticed Ross standing in the corner, ogling my body and sporting an erection. I woke up and tiptoed to the bathroom to wash my face and have a sip of water.

I passed by Ross's room and heard rhythmic squeaking of his bed. There was only one way to explain it. The only question was who was he thinking of while jacking off... I just smiled to myself and returned to bed.

Early the next morning, he drove back to the campus. Penny joined me an hour later. She seemed to be cheerful as usual. She French kissed me and said my son did such a great job, that she was tempted to use him again to fix a broken shelf in her kitchen and clean the garage. Of course, she planned to pay him. I laughed and said that if Ross had enough time for himself too, money was not needed. The subject was forgotten, and later, Penny and I drove to the nearest park and strolled hand in hand.

...

Time passed fast. Penny and I spent much of our time together on weekdays, but on weekends, I gradually saw her less and less. Lately, Ross also spent more time away from the house, declaring he made new friends that he liked. However, he insisted he'd be there for me whenever I needed or wanted him around. I wished to spend more time with him, but I was reluctant to burden him as he seemed to enjoy his time outdoors and always returned in good spirits.

Then the summer vacation started. It became uncomfortable: With Ross around, my intimate relationship with Penny suffered a downturn. I thought we could still be together at her home, but she claimed to have started several voluntary charitable activities, and we met at her home only twice a week. I attempted to busy myself too, but my physical needs, which were fulfilled on a daily basis before, and now were reduced to twice a week, bothered me. Noticing my son walking nonchalantly in the house with only shorts, sporting a woodie each morning, did not help. I got spoiled and needed more!

About a month into Ross's summer vacation, he went on a week trip to the northeast states with a couple of friends. My encounters with Penny resumed almost like before. On the 3rd day in bed together, Penny glanced at me for a long moment and blurted, "Jenny, I have to tell you something, but promise me you listen to the end, and be gentle judging me."

"Stop that. you are scaring me. What is it?"

"... for a month now, your son and I have been having sexual relationship..."

"Whaat?..."

"Remember the first time he came to fix the fence? It was a hot day. I was tanning while having on my black bikini. Ross worked on the fence and started sweating. I offered him lemonade from the pitcher I had before me. He drank it while ogling my tits. Having a young guy staring unabashedly at my bosom was too tempting. I asked him to spread suntan lotion on my back. He did a great job. In order to rub it evenly, I unclasped the back straps. When he finished, I turned on my back and joked if he was interested in doing the same to my front. You should have seen him. He had a huge tent in his shorts and didn't know how to answer. I told him to come closer. When he did, I told him that if he smeared the lotion nicely on my front, I'd take care of his 'big problem'. He began doing my shoulders and hesitantly moved to my upper chest. I gently caressed the front of his shorts to encourage him and jiggled my chest, which inevitably loosened my top, and it fell on my lap. He gasped and almost came right there. I said, 'Ross, your issue is more urgent than my suntan lotion. Let me help you first, and then you'll finish massaging the lotion on my body and fix the fence.' To cut the story short, I gave him a blow job with a happy ending. After he finished the fence, I was so grateful, that I let him fuck me. Since that time, every weekend, he was coming to my house and cumming in me. There are 2 reasons I tell you about it now. The first one is obvious: I feel guilty fucking your son, especially since I have intimate relationship with his mother too. But the second one is even more important. In case you haven't noticed, your son is in love with you. Yes, he loves to use my body for sexual gratification, but his ultimate dream is to have you. Twice, as he climaxed, his eyes were shut, and he mumbled, 'Oh Mommy, your body is so sexy... I love to fuck my MILF...' After the second time, I confronted him about it. He attempted to deny it, but I could see he was lying. I told him it was OK. I knew our relationship was purely physical, and I did not expect him to love me. I never felt that I was being used by him. We both enjoyed our sessions. After an hour, he admitted he saw you more than just a fantastic mother. He confessed that on multiple occasions he sniffed your underwear, and masturbated while fantasizing about you. Jenny dear, as I said, I am so sorry I did things behind your back, but I really love YOU!"

Penny's confession took my breath away. I was stunned and had no idea how to behave. Penny kissed me gently and blurted, "Ross will be back in 3 days. What do you want me to do?"

"I have no clue. I didn't have time to digest the news. I am still shocked by the revelation."

"Jenny, during the next 3 days, we have to come up with a plan. You'll be the ultimate decision maker, but let me give you the options: 1. You choose never to talk to me again and order me to stop seeing Ross. 2. You decide to continue everything as is. 3. I continue with you OR Ross and leave the other one. There is a 4th option, but it's feasible only if you are REALLY into it..."

"You betrayed me for not telling me about what happened after the first time. You are my BFF, and nobody else comes close. I do not wish to leave you, though I may never forget your transgression. My son is no longer a minor, and he can have relationship with whoever HE chooses, so I cannot prevent him from seeing you. In summary, neither option is desirable. What is the 4th one you mentioned?"

"... how much do you love Ross?"

"What a silly question! I am willing to die for him."

"That was not what I meant. Do you find him only a terrific son, or you see him as a mature young attractive man?"

"Both."

"To say it bluntly, the 4th option is Ross and you having intimate relationship with or without me..."

"Penny, you are nuts! You expect me to let my son insert his dick into the same hole he came out of?!..."

"Honey, I love you, and as I said: YOU DECIDE. But if you see him as the new man of the house, and a reincarnation of your late husband, Why not? We both have physical needs. We tried to enjoy together, and I loved every minute of it. However, neither of us is really a 'pure lesbian', so rather than overthinking about the sigma of incest, if a young, attractive guy finds you highly desirable, I think you should at least consider it..."

"Penny, I am tired. Please go home and leave me alone."

She tried to kiss me, but I turned my back on her. At the door, she said, "Jenny, you may hate me now, and it's understandable, but I love you with all my heart, seriously. I'll call you in am." I didn't bother reacting and heard the door closing behind her.

I grabbed a bottle of Chardonnay and a large plastic container of chocolate ice cream and began eating it with a spoon. My mind was spinning: Was I too focused on my own happiness? How did their affair happen under my nose without me noticing it? Each option had obvious and unforeseen risks.