My Daughter's Boyfriend Caught Me

Thanks to JOP for the ideas.

The story does not contain sexual involvement of a person under 18.

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Sally and I got married 22 years ago. She was my sweetheart for more than a year before our wedding. She possessed everything a man can ask for in a woman: Pretty face, gorgeous body, gentle demeanor, uncanny wisdom, fun to be with, and most importantly, great chemistry with me. If you are curious about our sexual compatibility, it was as good as it gets, or at least this was the way I interpreted it.

Our daughter, Nora, was born 2 years later. As a child, she was average looking and an average student. Everything about her started changing as a junior in high school. She remained quite short and rather skinny, but her face slowly changed and reminded me of her mother when I first met her. She became more serious about her studies, and in most subjects her score was an A.

Nora got accepted to UCLA, and currently she is a sophomore. Sally and I couldn't be prouder. About a year ago, she began going out with Ryan, who was a year older and also studying at UCLA. She was majoring in the arts, and Ryan in engineering. They've met at a party and clicked rapidly. We first met Ryan about 4 months ago. He was dressed nicely, behaved politely, and made a good impression on Sally and me. Two months later, Nora asked us to let Ryan move in with her at our house. The house was not far from the campus, and the couple seemed happy together, so we agreed.

In the mornings, each one had a different schedule. Mine was the easiest: As a freelance CPA, I could arrange my itinerary as I pleased. Sally worked as a receptionist in a dentist's office, and left home at 6:45 am every weekday. Nora and Ryan left the house together on 3 days, but the other 2, each of them left at a different time. Most evenings, the 4 of us ate dinner around 7, unless somebody was out. Nora and Ryan's bedroom was upstairs with their own bathroom, while Sally and I slept downstairs. The arrangement worked well for everybody for the first 2 months.

...

One morning, after both Nora and Sally left the house, I was in the kitchen, drinking my coffee and watching the news, when I noticed Ryan walking downstairs from his bedroom. I've seen him coming down before, but this time it was different. He wore only shorts, and a huge bulge was seen in the front of his pants. If it were a small tent, I wouldn't notice it, but it was massive and pushed his shorts like a gigantic utility pole lying down. It was so unexpected that I could not take my eyes from it.

Ryan smiled, "Sorry, Jim, I need to go to the bathroom, but decided to have a cup of orange juice first."

I didn't answer, and my eyes kept following his humongous member. He drank his juice nonchalantly, watched me ogle his erection, and slowly moved to the bathroom. I continued staring at the news on my computer, but the sight of his enormous bulge never left my eyes. When Ryan exited, his shorts looked normal again.

He grinned at me, "I'll put a shirt on and go visit a friend of mine. Our professor is sick and our first hour will be at noon." Fifteen minutes later, he was gone.

As much as I tried, the unusual vision of Ryan's giant bump refused to disappear from my mind. It caused a strange feeling; a combination of surprise, fear, excitement, and even arousal. I wasn't sure why the arousal, because until that moment, I was strictly heterosexual. I was happily married, enjoyed sex with Sally, and never thought about another man's body before. Well, assuming that I'll ignore the one time Tim and I got drunk in college and masturbated each other to completion.

I attempted to concentrate on other subjects: Mr. Robin's tax return, the Lakers win over the Timberwolves, the shelf I promised to fix before the weekend. However, nothing helped. The massive tent never left my brain. I was becoming horny... WTF!

I chose to look at some porn and jack off to calm down. I started with a threesome of 2 guys and a girl. The men capitalized on her mouth and cunt, respectively, and together managed to make her cum multiple times in a row. Then one of them climaxed in her pussy. When he disengaged from her vagina, his dick was still leaking. The other guy changed into a 69 with the woman, and after a couple of minutes, stopped eating her. He grabbed the other guy's cock, inserted it into his mouth, and hungrily sucked him. Shortly after, both men reached a happy ending. It was so hot, that my pecker jolted, ready to erupt too.

When the clip ended, I moved to watch another one. This time I selected a gay porn. I removed my pants and briefs, began masturbating, and watched a smaller man adoring another guy with a long tool. He caressed, rubbed, and then licked the tip as the bigger man smiled at him and encouraged him to take it into his mouth. Soon after, the shorter guy opened a big mouth and took in about half the organ. He started bobbing it, gradually taking more of it inside his oral cavity. The scene was erotic as hell, and I felt I was about to ejaculate.

All of a sudden, from the corner of my eye, I saw a small movement. I turned my head to look at it, and my blood froze in my veins: Ryan was standing behind me, gazing at the screen and obviously aware of what I was doing. I tried to stop the video, but couldn't move.

Seconds later, Ryan moved closer to me and said, "Jim, that's OK. Don't be bashful. Watching porn is normal. Here, I'll do the same." And as he was talking, he removed his pants and underwear to reveal his organ. It was at half mast and looked like 7" or more already.

As the action on the screen continued, he began masturbating before my eyes. His eyes were directed at the movie while mine were focused on his member that continued growing and stiffening before me.

I was sitting on my couch, and Ryan was standing by my side. He closed the distance between us and blurted, "Jimmy, earlier I noticed your fixation with my erection. And now you find it more interesting than the video. You can touch it if you wish."

With my eyes still mesmerized by his magnificent monster, I mumbled, "I am not gay..."

His hand caressed my hair, "I know. But you are curious, and there is nothing wrong with it."

I hesitated for a moment, debating whether to do it and satisfy my cravings or pretend I wasn't interested. Being extremely aroused tilted the decision toward the first choice. I touched his thick, veiny shaft with 2 trembling fingers. It was slightly hairy, soft outside with the foreskin folded back, and the middle part was rock hard. The purplish head was spongy with a small slit. I barely touched the helmet, and a drop of precum oozed from the hole. I rubbed it onto the head, and another drop appeared on top.

The whole scenario was unbelievable: For the first time in my life, I watched gay porn while masturbating and playing with my daughter's boyfriend's cock... The mere thought of it increased my arousal further. My lips felt dry, and I licked them.

Then I heard Ryan mutter, "Go ahead, Jimmy. I know you want to. Lick it and get it over with."

I lifted my face and glanced at Ryan's eyes. There was no sign of snickering. I hesitated. Yes, I wanted to taste the drop, to feel his beast with my tongue and lips, but was reluctant to cross the line.

Next, I felt Ryan's hand gently nudging my head onto his erect pole, which by now seemed to be more than 8" long and VERY thick. And then my lips met his warm flesh. I sniffed it, feeling its soapy, yet slightly musty odor. I tasted the drop with my tongue. It was a mild, minimally salty, not bad... I kissed the tip, hearing Ryan groan. He pushed it mildly onto my lips, and they parted. I remembered Sally always loved to give me head, telling me she liked my pacifier in her mouth and hungrily drank my juices. My erect penis ached, wishing to spew its contents as my lips opened wide to accommodate Ryan's rod. It filled my mouth to the rim, and I struggled to breathe, but Ryan was patient and didn't move, allowing my cavity to gradually dilate and be more comfortable with it inside. As my respiration improved, I slowly allowed more of it to penetrate my mouth. It was huge, but softish on the outside, and my abundant saliva facilitated its sliding in. When about 3" of its base was left out of my mouth, I felt like I was about to choke. I stopped there for a moment and then started bobbing gingerly, using the same technique Sally blew me. The beginning wasn't easy: I was never trained to have such a large foreign body in my mouth before, but gradually I started liking the feeling. I accelerated the rhythm somewhat, and my hand caressed gently his heavy sack. He murmured, "Jimmy, you are terrific."

Probably because I was very horny too, his words sounded like a wonderful compliment. I intensified my bobbing and began jacking off myself. As I was closing in on my eruption, Ryan tensed, his hand held my head in place, and a stream of massive proportions started flooding my mouth. Instinctively, I swallowed as fast as I could, but after about 20 seconds, I felt some of his slimy spunk dripping from the sides of my mouth. My orgasm took place as his juices dwindled to a trickle. It was a powerful one.

Ryan's organ was shrinking in my mouth, and he pulled out. I gazed into his eyes to see his reaction. His eyes were warm, and he said, "You were awesome!" His finger traced a couple of his goo drops off my face, and he stuck them into my mouth, saying, "I think it was the best BJ I ever received. Thank you. I need to dress up and leave now. Of course, nobody will know about what happened here. Next Tuesday, my first class starts at 11 am, so if you are in the mood for a repeat, let me know. Take care."

I sat there, still stunned by what had just taken place: I was an older, heterosexual, happily married man who sucked a much younger, hung guy's cock and swallowed his stuff without blinking an eye... And the worst of all: While I felt somewhat guilty, I had no remorse, and didn't suffer a bit! Would I ever do it again? Probably not, but the overall experience was positive.

...

Most of the day, I was home. I worked on the accounts of several clients, but my head was somewhere else. The day's event kept repeating over and over, and I could only hope I did not screw up my customers' numbers.

Later in the evening, when both Sally and Nora were home, Ryan behaved like nothing had happened. His demeanor and jokes were as usual, and neither lady suspected anything. I was quiet, and Sally asked if I felt OK. I forced a smile, "Everything is all right except for a mild headache."

After the dinner, all 4 of us sat to watch a movie on Netflix. Sally cuddled up to me while Nora and Ryan sat on the other sofa, hugging. It was one of Tom Cruise's Mission Impossible movies, and we all enjoyed his amazing stunts. When the movie ended, Sally told me, "Honey, I am tired. Do you mind if we go straight to sleep?" I smiled, "No problem," thinking that since I came earlier, it was a good idea...

...

In the days that followed, being alone at home most of the day allowed me ample time to think about everything. The first day was the hardest: I was torn with guilt and shame, and my work suffered. The second day was easier, and recalling that the wild experience was physically pleasurable, I opened my computer to watch some porn. I started with vanilla sex between a man and a woman, and then moved to lesbian action. Both subjects were somewhat arousing, but not enough to make me climax. I tried to watch a clip of a threesome, but in this one, the 2 men only interacted with the woman, and again, my arousal state wasn't high enough to reach an orgasm. In desperation, I opened a gay video. It started with a farmer accepting a new young employee. On the first day, the farmer showed the young guy how to do everything. As expected, the untrained youth ended up with muscle cramps and could not move from bed the next day. The farmer made the new employee remove his clothes and started massaging his legs, shoulders, back, and ass. Close up shots revealed the young guy developing an erection and slowly spreading his thighs. The farmer noticed this reaction and ordered the guy to turn over. The guy blushed but did as told. The farmer smirked, "I see you like to be touched by a real man, aren't you?" The guy admitted that the rough massage made him horny. The farmer said, "I will continue, but you should do something for me too." "ANYTHING," said the young guy. The farmer unzipped his fly, exposing a long, steely hard, uncircumcised cock. "Suck it first!" The young guy was shocked, but eventually took the raging organ into his mouth and milked it. As the sucking noises were heard, my own penis engorged, and I was close to coming. The farmer rubbed the guy's pectorals, kneading his small breasts, and did the front of his legs. Then he commanded the junior to turn over again and stay on all 4. When the guy obeyed, the farmer climbed behind him and blurted, "It's time to learn how farm animals have sex." Subsequently, the farmer spat on his palm and fingers, lubed the guy's anus, and gingerly invaded him with his tool. Watching that scene, I became so horny, that I hardly touched my dick and immediately ejaculated.

I closed my computer, lay in bed, and acknowledged to myself that gay porn became my favorite go-to sex scene. Then I remembered Ryan's meat. It was marvelous: Both its appearance and... taste. I missed it already. And despite cumming only an hour earlier, my prick began rising again!...

The same evening, before going to sleep, Sally hinted she was in the mood. She sucked me expertly, as always, but my organ reached its maximum size only after I imagined Ryan's cock down my throat. I pounded my wife for a long time, thinking about Ryan's pecker getting hold of me. When we finished, Sally kissed me and mumbled, "I see you love my new perfume. You fucked me like a young stud..." I whispered, "Honey, what can I say: You are very sexy."

...

On Tuesday morning, I got cold feet. I stayed in my room until 9 am. Then I showed up with pajamas in the kitchen. Ryan wore shorts, ate a sandwich, and drank orange juice. He didn't bother looking at me and blurted, "I am done here. I go upstairs. I'll be leaving for school in an hour and a half."

I ate cereal, debating what to do. I was scared to admit I wanted Ryan's cock. I craved it, yet frightened of the consequences. It lasted for half an hour before I gave in to my needs. I knocked on his door. "Jimmy, come in. It's open."

As I opened the door, I saw Ryan smiling broadly at me, "I knew that sooner or later you'd get the courage to show up." He was naked in bed with his right hand slowly rubbing his massive tool. He pointed to his huge erection and said, "Here Jimmy, kneel on the carpet and have your favorite pacifier."

His words, and the way he said them, were demeaning, but one look at his rigid tower was enough to melt my heart. I stayed by the bed on my knees and gently massaged his amazing thing between my palms. Soon, I bent my head, parted my lips, and engulfed the crown, milking it lightly. This simple action aroused me, and my penis pressed against my zipper. Gradually, more of his mammoth member penetrated inside. Learning from my prior experience, I was able to take all but 1.5" into my oral cavity before gagging. Ryan moaned loudly, blurting, "You are excellent. So much better than your daughter!" For some reason, likely because I was very horny already, his talk filled me with pride, and soon I accelerated my ministrations. I was sucking him fast and furious while playing with my own member. I timed it right, and we both orgasmed simultaneously. After successfully swallowing ALL his delicious goo, I licked the stains from his deflating rod and stared at Ryan with a happy grin.

His fingers combed my hair, and he muttered, "You like blowing my big dick, that's good, because I like the way you do it. If you wish, we can put it on our schedules. Tuesday mornings are best for me because my classes start at 11 am or even later. Would you like it?"

I lowered my head, and whispered, "I'd love it."

He added, "One comment: Occasionally, on Tuesdays, Nora wakes up earlier than usual and has the urge to be thoroughly fucked. I won't know if it will happen until that day."

Ryan dressed up, with his bulge slowly decreasing. He gave me another smile and left. That day and the next few days, I felt better; both physically and mentally. I accepted my new fate: Being happily married to a good wife, having a nice daughter, and once a week, enjoying giving oral to her boyfriend. Surprisingly, Ryan and I learned rapidly to behave as usual in the presence of our mates.

...

The following Tuesday, the mere thought of having Ryan's beast down my throat made me horny, and even without touching my organ, it was directed straight up. I was so aroused, that I was salivating. Five minutes after the girls left the house, I was in Ryan's room, wearing only shorts. I saw him naked, lying supine with a smile on his face, "Your daughter needed a good fucking this morning, and I complied. I don't feel like going to the bathroom. Will you be nice and clean the mess before I let you use it as a sucking tool?"

My hesitation lasted a few seconds. It was amazing to think what being horny could do to a man's brain: I licked and lapped his resting prick as well as his hairy sack. The taste was different than before: Nora's juices coated Ryan's shaft, and I savored them... The thought of swallowing my daughter's secretions was both scary and, for unknown reasons... exciting too.

I milked Ryan's cock dutifully for about 15 minutes before he dumped his load deep in my mouth. After we were done, he was very cheerful, saying, "I love the idea of having vaginal sex with the daughter, and subsequently having her father cleaning the residue and finishing me orally." My face got flushed, and I did not say anything.

Before leaving, Ryan said, "Jimmy, you are a great cocksucker, and we both love the feeling. But seeing you like to watch gay porn, it occurred to me you might consider anal sex as well. I am not pushing, of course, and having sexual intercourse with Nora is fine. However, if you become curious about it, don't be shy and notify me." He didn't wait for my answer and was out the door seconds later.

I remained with my mouth open. For 2 weeks, gay porn became my go-to for jacking off. Taking Ryan's gigantic member in my mouth was doable, and I controlled everything. On the other hand, letting this enormous dick near my puckered hole was asking for trouble. There was no doubt he would rip my sphincter, and I'd end up needing urgent surgery to fix it.

For 2 days I was thinking about the issue. Then I googled the question: What is the largest girth penis that can enter any anal sphincter? On Reddit, multiple readers offered advice. The summary was clear: Theoretically, every sphincter can enlarge adequately with the right preparation. People have suggested starting with small dildoes or butt plugs, and gradually moving to larger tools. Everybody emphasized the need for patience and plenty of lubrication to reach the right width. The length was usually less important, at least until 12". The articles were encouraging. I had until the upcoming Tuesday to make up my mind.

...

On Monday, I met Rachel Krugman, a client I have served for 3 years. She looked different this time: The first time we met, she appeared timid and was dressed conservatively. I attempted to make her feel more comfortable and made some jokes as well as complimented her. The second time, she was more smiley, and our work on her taxes was more pleasant. We even talked about our private lives. This time, Rachel wore a short beige dress with ample cleavage, which emphasized her voluptuous body.

I smiled at her and said, "Rachel, you look stunning. However, I have to warn you that as a normal man, my eyes may wander from calculating your taxes to your perfect figure."

She grinned, "This was my intention. Anyway, let's finish with the necessary work first."

It took me half an hour to work on her taxes, and she was happy to find out that, assuming my calculations were right, she'd be getting back thousands of dollars from the IRS. She smiled broadly and gave me a seductive look, "Jim, when I first saw you, I was intimidated by you. Your decisions could cost me my life savings, but you were gentle and understanding. Next time, I noticed how handsome and smart you were, and I got attracted to you. Today, in addition to working as a CPA, I wanted to tell you that if at any time you wish to see me for a more pleasurable reason, I'll be open to it." She handed me her phone number, winked at me, and left.

I attached her phone number to her file, but knew I'd never do it. I loved Sally too much to cheat on her with another woman.