So Sophomoric Ch. 01

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Mother helps son adjust to being a bisexual cuckold.
5.5k words
4.3
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Part 1 of the 2 part series

Updated 06/07/2023
Created 08/21/2015
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A lot of things changed for me during my sophomore year of college. Like most of my peers, it was a time of sexual exploration, but unlike most of my peers, I was exploring bisexuality, cuckolding and incest. At times humiliating and at times heavenly, as my college years drew to a close at graduation, I realized I hadn't psychologically processed the earth shaking, mind blowing experiences that had changed my life forever.

As soon as I graduated and entered the workforce, I sought out a therapist to help me understand the events that transpired, and what it all means for my identity as a man, my masculinity. Of course, Mom came with me from the very beginning. We needed couples' counseling in a million different ways, many of them unique to the mother-son relationship that was the foundation of our physical love.

Luckily, we were recommended a really great and totally understanding therapist. Lisa has been totally accepting and even encouraging of our continuing romantic and sexual relationship. It was Lisa that suggested I continue to call Mom 'Mom' instead of 'Sandra', her first name. Lisa said it was important that we always keep the mother-son relationship primary. She also recommended that I write about the events that transpired, and post the story in a public place on the internet. She said she wants me to think through things and remember what happened in a public space, and she wants the feedback I receive, whether good or bad, to be incorporated into our counseling sessions. So, here goes... Please feel free to comment as much as you like.

During the summer after my freshman year of college, I lived at home and was kind of sad about my first relationship ending with my first break up earlier that spring. The first weekend I was home I saw first hand how sexy my Mom was dressing these days. Mom went out for drinks with her girlfriends dressed to kill in spandex blue jeans that show off a woman's pantie lines and curves. Dad took her out to nice restaurants and she would wear short skirts with him. Despite this though, Mom and Dad seemed to be arguing more, and I figured that had something to do with why Mom had started dressing so seductively. Either Mom was getting laid somewhere else, or she had begun dressing sexy for Dad in a last ditch effort to salvage a loving relationship with him. They had always been on the verge of divorce because of him cheating on her, but something made me think that a divorce might be coming sooner rather than later.

I knew Dad liked her change of dress at home, and I wondered if he could tell that I did too. Last Christmas he had bought a short-short red nighty for me to give her and wrapped it himself so that I didn't know what it was. It was really embarrassing for both of us when she unwrapped it under the tree Christmas morning and thanked me with a tight hug. I hadn't seen her wear it much after she tried it on for us that day, but now it had become her favorite thing to wear around the house, often without panties, I noticed. This blew my mind, and after catching her bent over a few times, I think I subconsciously became infatuated with hairy cunts and big asses.

I didn't do it on purpose, but it just started happening one night after going to bed... my feverish 20 yr old mind would dream of fucking and making love to Mom. The way she was showing off her assets around the house, I could easily see that she had very large nipples on her perky little tits. She was so sexy, short, curvy and cute. She looked amazing and what drove me crazy was that she routinely wore only a t-shirt and panties around the house, giving me non-stop eye candy, a view of the hairy cleft in the space between her thighs, that juicy spot where here ass cheeks collide with and celebrate the thick split lips of the Mommy pussy I could only imagine.

One day as we were all getting ready to go for a swim in the pool, I accidentally walked into Mom and Dad's room to find Mom laying back on the bed with her legs spread eagle, hard nipples pointing straight up, and a beautiful, dark and thick bush surrounding a slightly parted pussy, the fingers of one small hand working a swollen clit. She practically screamed, and I only had a second to memorize the beautiful vision. That was a turning point though, the day I consciously realized that my own mother was so completely and beautifully fuckable that I would do anything, absolutely anything, to return to my origin, Mom's dark, angelic and hairy pussy. A strange thing for a 20 yr old to think, but I prided myself on being a free thinker. Mom's thick ass was world class, and I was only being honest to want to let her know somehow that I appreciated it and was glad to see it everyday, as well as her beautiful face of course, and pointy perk-tits.

This was completely out of character for me, but I mention it to emphasize how completely possessed by her erotic body I was - I was literally out of my mind. So, after having briefly caught her rubbing her beautifully hairy, spread eagle pussy, later that day when we got into the pool, and while Dad was getting another beer, I swam up to her and cupped one of her a little titties and fat ass cheeks in each hand... and bit her neck from behind. She giggled, and quickly screamed and swam away. When she turned back to face me, her face was blushing bright red and she looked very unhappy with me. We were panting, in shock, out of breath, but I just laughed it off and said "Sorry." She laughed a bit too, but raised an eyebrow at me, we both flushed red, and things got back to normal.

***

I give you all of this information only for background, but now the real story starts to begin. My sophomore year of college, I met the love of my life. I hadn't met many Asian girls and thought they were beautiful. Wei was the most beautiful. We met in the laundry room of our dorm. It turned out that we were hallway neighbors. We quickly became friends, and after some hesitation on her part, we became inseparable lovers. She had the same 5'4, curvy body that Mom had, and the same hairy space between her thighs, below her cunt. She was a virgin; I was her first. It was true love.

Fatefully, I also met Simon that same year in the same dorm. He was playing a guitar in the smoking area by himself. I sat down next to him and started smoking. I started up a conversation with him. Although I didn't recognize it at the time, he is a very handsome man, slightly taller than me, stronger muscles, but not a jock. He was definitely an Alpha male... the kind of artist or musician that has no problem getting beautiful women into bed with him. I even found myself wanting to endear myself to him or impress him in some ways. We quickly became best friends. When I wasn't with Wei, I was with Simon, and vice versa.

Simon was very charismatic and usually had one or more incredibly sexy girls in his life. For my part, just being alone in private with the woman I loved, being with Wei felt so perfect and beautiful. I felt truly blessed to be with her and could never imagine cheating on her. Simon on the other hand seemed to begin a new relationship long before the previous one formally ended. He was a heart breaker. Being his roommate, I knew beyond a shadow of a doubt that he was also an amazing love maker. Judging by the screams of pleasure that frequently came from a woman in Simon's bedroom, I understood why they were so devastated to see him go. He was an amazing fuck.

On the spur of the moment, after our finals were over, we went on a road trip to Branson, MO of all places. We took turns looking at porn while the other drove, and soon we were both sporting massive hardons. I've always liked to show off my free thinking side. Simon was driving my car on our way back, and I was looking at the porn. I thought to myself, "Wouldn't it be funny to jerk off really fast while he's driving?" I might have no other choice if I don't stop looking at these beautiful Vietnamese women's hairy bushes.

We had smoked a bowl a few miles back at a rest area and heard some trucker getting a blow job in a restroom stall. Maybe thats what had unconsciously pushed me into sexual overdrive when we got back in the car. When we heard it, we both looked at each other to confirm what we were hearing. The look on Simon's face told me that we were both hearing it. He was still silently laughing with me as we listened to someone's face getting fucked and gagged hard and went ahead into the stall next door to smoke some weed. Smoking with Simon somehow always seemed to be better than with other friends. We seemed to connect and really understand each other. We were into the same things. From the looks of the interior walls, this was a known cock sucking spot, and the continuing lust in the stall next door was just heating up. It was almost romantic, some how.

After he was done smoking, Simon unzipped his pants and whipped it out for a piss. I tried not to look, but heard him depositing a thick stream of piss into the urinal next to me. For a brief instant, I wondered if that meant he had a big dick, the fact that his piss stream was so loud; automatically my eyes darted down to watch him pee for a split second. I had always kind of assumed he did have a big dick since the girls got so hot with him, which is a weird thing for a straight guy to think about their best friend, I guess. Even though he caught my quick glance and started laughing AT me instead of WITH me, I obtained the information needed to satisfy my curiosity. He was hung.

With everything going on, I was having stage fright and couldn't pee, so when Simon left, I got in the squatting position, hoping that peeing like a girl would unbottle the unbearable pressure. As luck would have it, the stall didn't lock at all, and I could still hear the guys next door going at it, brutally and obscenely. A shiver went up my spine as I thought about the potential danger of lingering here very long - I might just get a cock unleashed in my face. I pushed, and an almost orgasmic blast of streaming piss shot into the commode. It felt like my relief was a balloon that had been emptied, and oddly my dick immediately got hard when I finished. The sounds of a man's orgasm as he pumped cum into a faggots mouth and throat filled my ears, and I got fucking hard.

Back in the car, after a few miles, I went ahead and told Simon I was going to jerk off, so don't look. He was shocked at first and said No, but stared at my dick when I pulled it out. He slowly started laughing. I was hard, but I guess he thought I was small. I didn't care, I just wanted to bust a nut, and thats exactly what I did in about 5 minutes flat.

After I clean myself up, I notice the car swerving a few times and see that Simon decided he needed some relief too. With a cigarette in one hand, and his dick in the other, the steering wheel wasn't getting enough priority. I told him "Pull the fuck over dude, you're going to get us killed!"

He said, "No way, 2 more hours of driving and we're even, then I can go to sleep until we're back at the university. If you don't like my hand on my dick, you can just suck it for me instead, cuz you've already got yourself off. Don't be a hypocritical pussy, get your lips on my dick, Joey."

I was fucking shocked frozen. I didn't think that our dynamic was like this at all, but his tone had gotten more and more disrespectful. I felt my dick involuntarily surge as I listened to his words and slowly gazed down into his lap, where the most magnificent cock I could have ever imagined was right there before my eyes in all of its impatient, masculine glory. I became entranced. I think Simon recognized my inevitable submission, and became kinder towards me, like the friends that we were. He told me no one would know, that it was only fair, that it was safer... even that, hell, I might kind of like it. I shook my head violently at the thought and he laughed more, calming me and getting me used to the idea. He told me since I had a steady girlfriend and he didn't, it was obvious I'm not gay, and neither was he. He told me he just needed to get off really, really bad and asked for this one favor as a friend.

Still mesmerized, his words began to make sense to me. The reluctance was bleeding out of me as he spoke. He looked into my eyes; his poetry worked its way into my heart. My dick was getting hard again; we stared into each other's eyes... The vehicle swerved again as he stayed, lost in my eyes, staring into my soul for too long. I knew what to do. I went down on him.

This first time, I was in shock. I blacked out a little bit. I don't remember enough to describe what occurred then, but this is what I do remember: His dick head was big, twice the size of mine. He was rock hard, several inches longer than me. His dick actually curved downwards. Its a rare shape, but I immediately loved it. The head barely fit between my lips, but it had more room as it pushed into my mouth towards my throat. Simon pushed my head down and the head popped into my throat, inches of thick dick slipping deeply into my face and neck, stretching my very existence open for an Alpha male's pleasure. I blacked out.

I woke up choking, gasping for air as Simon pushed me away from him. The cum that hadn't shot directly down my throat and into my stomach, sloshed out of my mouth as I raised up to a sitting position, feeling very used and degraded, still not in full control of my body. Then I noticed a wet spot in my pants and realized I'd even cum while I was comatose. I was amazed. I felt truly embarrassed as I looked over at Simon, looking him in the eyes for the first time as his personal cock sucker. He made everything feel OK somehow. Like I said, he was charismatic. I felt safe and knew that I would do it for him again whenever he asked.

Then I remember Wei How could I have not even thought of her once throughout the whole ordeal. It was Vietnamese pussy that had made me so horny that I decided to jerk off to it in front of Simon, thus virtually sealing my fate. I love Wei more than anything, and couldn't bear the thought of her knowing what had just happened. I grew frightened and looked at Simon pleadingly, "Please, whatever else happens, please don't let Wei know what I just did. I don't know how she would react, and I want to stay her boyfriend. I love her and would never do anything to hurt her or lose her, but I do want to suck you off again, if you want it... anytime, I'll suck your dick again anytime, dude." My face burned a bright red. The look in Simon's eyes became one of possession over me instead of friendship towards me, but still, I trusted him. You could almost say I was falling in love with him.

That night Wei came to bed with me like usual, and was really horny, but I was worn out and disappointed her. As Simon came to rely more and more on my mouth as his cock-home, I was less and less able to perform with Wei.. Since my dick continued to explode on its on when Simon fucked my face, I just didn't have enough sexual energy to please Wei the way I used to.

It was a dangerous game I was playing with the two of them. We started hanging out as a group of three more and more often, and that called on me to suck Simon off in closer and closer proximity to Wei We all really loved each other's company though, and looking back, those months and the years that have followed have been the best times of my life. I owe everything to this trio of friendship and my Mom.

I could tell Wei and Simon were deeply attracted to each other. We were honestly such good friends though, that I think they tried to ignore the attraction. I did notice quite often though that Wei would be more flirtatious with him after another failed attempt by my practically impotent little dick to perform. I wanted her to get fucked by a real man even then, I just didn't know how to articulate the desire. I felt she deserved to have her itch in life scratched by someone she liked and that could get hard, she needed that masculine satisfaction. The pit of my stomach began to butterfly as I watched their interactions become more and more intimate, if not overtly romantic. I mentioned none of these thoughts to either of them, but did encourage the flirtation any way I could without being obvious.

After a couple of blissful months as a mostly Platonic threesome, I got a disturbing call from Mom. Her and Dad were getting a divorce, and "Could you come home this weekend? I really need a shoulder to cry on."

This would be a big step for our trio, leaving Simon and Wei alone together for a weekend, as I knew they would hang out just as much without me. I wondered if anything might happen between them, if their intimacy without me might blossom into a stronger love or desire for each other, altering the dynamic forever - having been sucking him off and unable to satisfy Wei for months, I knew it was a perfect combination for the two of them over a weekend alone. But without hesitation I told Mom "I'll be on my way as soon as classes are over. I love you."

I told Wei I loved her and that I would be gone for at least a three day weekend, maybe longer if Mom needed me. She understood. I told her that "Simon could take good care of you if you need a man for anything while I'm gone," and a nearly fainting shiver running through my body at the innuendo. She smiled and said, "Yes..."

***

Immediately after I rang the door bell, Mom was opening the front door. She must have been watching for me. When that most beautiful of all forms, a man's mother stood directly in front of me through the threshold, I know I blushed big time. She was wearing the skimpy red nightie I had bought for her years ago at Dad's behest, and I could tell from the back lighting of the room that she was pantiless. I admired the width of space between her curvy thighs, showing off the cleft that draws one into an abyss of dark pink pleasure, hairy Mommy pussy, every son's delight...

We embraced. She kissed up and down my neck and cheeks which was really weird, but felt amazing, almost as amazing as her rock hard, eagerly elongated nipples. I bit the shit out of them later that month, but if you had told me that then, I would never have believed you. We headed to the living room where Mom offered me the water pipe. I was soon high as fuck. So was Mom. We decided to kind of cuddle on the couch as I comforted her and listened to everything that had happened. I knew Dad was to blame for it all, and was glad to see him go. Mom deserved better, Mom deserved me.

Nothing much more happened on that visit. We became comfortable around each other half naked, and hugged, cuddled and kissed a lot, but we slept in our own beds, and nothing got out of hand. I figured the powerful weed we had smoked the whole time caused the heightened state of sexuality and intimacy between us. After all, I could literally smell her arousal while watching a movie with lots of sex scenes.

***

I never found out what Wei and Simon did while I was gone. They both acted kind of secretive or evasive about it. I figured they just got drunk and didn't remember much. But, as fate would have it, on my birthday Wei had planned a surprise visit to my room after classes when she knew I would be either studying or taking my routine nap. As I was to later discover, she wore only a bath robe, literally, when she came to my room. I would also realize then that Wei and Simon must have become intimate, must have fucked, while I was gone, for reasons that will become clear as I continue.

Simon didn't care that it was my birthday one bit, but he surprised me with a visit that afternoon as well - he needed his cock pleasured and sucked and knew that I was just the guy to do it for him. I hadn't been able to say no to him one single time since our FWB relationship began months ago. But I was still madly in love with Wei and felt ashamed of myself for not being able to satisfy her anymore. Whats worse, I had actually imagined Simon taking her from me somehow. Of course, that was just in the most paranoid and jealously deranged corner of my mind, but it had occurred to me as a possibility if things continued like this.

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