Journal Entry: The Night I Gave Rick My Virginity Monday, June 1, 2026 – 7:30 PM
I don’t even know where to begin. My body is sore, my mind is spinning, and I think i can still feel him inside me hours later. I need to write this all down while it’s still burning in my memory.
My name is Adam. I’m 21, white, 5’3”, 120 lbs, short brown hair, brown eyes. I have always been the small/short boy and never got attention from girls. That said, once i started going to chat rooms i realized that I did get attention from men. For years I’ve fantasized about being taken by a man. Someone who would make me feel sexy, protected, cute, desired, and completely owned.
I talked to many men over the years, but nothing ever felt right until Rick.
At first, Rick was just a nice person to chat with. He was 52, 6’2”, 240 lbs with a some belly, very hairy body, short brown hair with gray at the temples, clean-shaven, and striking blue eyes. He worked as a medical lab technician, had been divorced a few years, and had two daughters in college close to my age. He lived alone. When i first started talking with him, i wasn’t really drawn to him, but we kept talking. He started off as a mentor — asking about my life, encouraging me, giving advice. Over time he slowly became more flirty. He told me how much he loved small, smooth, petite boys like me. He began gently pushing me out of my comfort zone. What started as friendly conversations turned into hours on the phone, then very explicit phone sex. He knew I was a complete virgin. He kept telling me that he would love to be my first if i ever felt i was ready, how he would love to have me and help me explore.
By the third month I was completely hooked. He had gone from “maybe i like him, but he is too old” to the man I desperately wanted to give myself to.
We finally agreed to meet in a public place first — a chain restaurant near his house — just in case either of us felt off. He lived about a 2.5 hrs drive from my apartment, but since he lived alone it would nice to just alone with him and not be rushed, and be discrete.
i actually followed through this time, took the 2.5 hr drive and met him. I walked into meeting place around 8pm, heart pounding. I spotted him in a booth. He stood up — towering over me. We hugged. He felt so big and warm. “Hey Adam,” he said with a warm smile, “I’m really glad you actually came, baby.”
We ordered drinks — I had a couple of fruity vodka mixes, he had margaritas. We kept everything innocent at first. After an hour, the alcohol helped, and I felt comfortable. He suggested going back to his house. “No pressure at all,” he assured me again. “You can leave whenever you want.” Just wanted to be where we could talk more freely.
I said yes.
His house was beautiful — spacious, on a big private lot with no close neighbors. The living room had thick beige carpet, warm lighting, and a huge L-shaped sectional couch. We sat close and kept drinking, sharing 3 bottles of wine. As we talked more, drank more, and got tipsier, the talk turned sexual.
He leaned in with a mischievous smile. “You know those white thigh-highs and garter belt we talked about…?”
I gave him a wide-eyed “OMG” look.
“I did lay them out on the bathroom counter… just in case things went well tonight,” he said. “One of my goals is to see you wearing them before the night is over.”
I was drunk and flirty, and spoke with a false confidence, I giggled and replied, “Well… it’s my goal to get in them for you.”
Things heated up on the couch. He pulled me closer. His big, hairy hands roamed all over my small body exploring me — squeezing my thighs, rubbing my chest, teasing my nipples - and finding more and more skin as time went by. I got bold and started rubbing his thick bulge through his jeans. We were both breathing heavier. He started to remove my cloths, first my shirt, then my shorts. His hands started to find their way inside the waistband of my underwear, i told him how i shaved everything earlier that day to prepare, he asked “..everything?” And i confirmed “i spent 2 hours in the tub today with a mirror, everything from neck to knees.. everything “
“You feel so good, baby,” he murmured. “So small and soft… you are exactly what I’ve dreamed about you.”
He eventually prompted me, as he was pushing to go beyond just rubbing on each other, “Remember what you always told me you wanted for your first time? On your knees?”
My heart raced, having memories of all the time we had sex chat or phone sex, and always telling him how i wanted to suck my first time from my knees. I slid down from the couch onto the soft carpet of the floor, and crawled between his legs. He unzipped and unbuttoned his pants and pulled them down at the same time with his boxers, revealing his thick cock. Seeing a real man’s dick up close for the first time made me nervous. It was heavy, veiny, already half-hard. I hesitated, took a deep breath, and decided to commit, I then leaned in and gently kissed his head. Looking up at him I kissed it again, licked it, then opened my lips and took him into my mouth. Once I started, I got lost in it. I sucked him slowly and lovingly while he groaned and stroked my hair, calling me his good boy.
After a while he asked me if wanted to keep sucking him, or if i wanted to try other things, being flirty i look up at him, pulled my lips off his hard dick, and asked him innocently “.. what other things?”. He looked down at me with a big grin, he then helped me up off the floor. My heart was pounding so hard as he led me down the hallway to the master bedroom. I didn’t say a word, but inside I was thinking, This is really happening. I’m about to lose my virginity.
In his bedroom he had the lights on bright. There was a king-sized bed with towels laid out, on the night stand was a jar of coconut oil. He clearly prepared and was hoping we would end in his bedroom, He told me to go freshen up in the bathroom with some clear intent. I slowly walked into the bathroom, and told him “.. I’ll be back..” as i closed the door.
The master bathroom had twin sinks and large white tiles. Right between the sinks, neatly laid out were the pair of white thigh-high stockings and matching garter belt. As i looked at them i thought to myself “oh my god, he actually did it…”. I stared at them, mentally preparing myself. I’m really going to do this. I’m going to dress up, turn him on and give him everything.
I took off my underwear and started dressing. I was clumsy at first — I didn’t know how the garter worked. I figured it out, then rolled the soft stockings up my smooth legs and clipping the straps. When I looked in the mirror I felt exposed, vulnerable, and incredibly sexy.
I slowly opened the door and walked back into the bedroom looking to Rick.
Rick’s eyes lit up. “Mmmmm… I am the luckiest man in the whole world tonight.”. He looked me up and down, i could feel his eyes completely taking me in, specially since i was now revealing my smooth private area to this older man for the first time.
He had me lay on my stomach. He warmed coconut oil in his hands. The sweet, tropical smell filled the room. “I love coconut oil,” he said softly while rubbing it all over my ass. “It feels warm… and it makes everything feel more natural.” He worked a finger into me, then two, scissoring gently. “You’re opening up so nice, baby. Such a good boy for Daddy.”
He rubbed his own cock slowly to stay hard while fingering me. “I love the smell of coconut oil. the only downside of coconut oil is that it can break condoms… but since we aren’t using any you won’t need to worry about that. Skin to skin is going to feel so much warmer and intimate.”
He rolled me then onto my back. I was frozen with nerves and fear as I looked up at this big hairy man between my legs. He rubbed his cock against my hole. I flinched and bucked the first two times as a nervous reaction. “Easy, baby… breathe for me,” he coaxed. “That’s it… you’re doing so good. Those little whimpers are so cute.”
I settled into position and stayed still, he pla es his head to my hole and started to push, i felt the pressure grow and grow until.. POP…his thick head opened me and slipped inside me. I gasped sharply. He kept pushing until all 7 inches were buried deep. The stretch was intense — burning, full, overwhelming. I whimpered and panted while he held still, talking me through it. “Look at me, baby. Feel that? I’m all the way inside you now. You’re doing so well… such a tight, perfect boy.”
He stayed deep inside me for a long time, letting me adjust, rubbing my stocking-covered legs and holding my hand.
Then he started fucking me. Then… the leaned over and kissed me deep, his tongue in my mouth
The kissing was a huge moment. He didn’t ask — he just leaned down and kissed me deeply while he was inside me. I was shocked at first, but I melted instantly. I kissed him back hard. It made everything ten times more intimate.
When he finally came, he thrust deep and unloaded inside me. I felt every pulse. He stayed buried while I processed everything in shock.
When he pulled out, a rush of cum leaked from me. He smiled. “That’s why I put the towels down, baby. Look at you… you’re gaping just a little. So cute. You were so tight, and now you can’t quite close all the way, and you are a little red, baby you look like you been fucked”.
After the first round I went to the bathroom to clean up. I was a mess — cum leaking, oil everywhere. I looked at myself in the mirror and started crying quietly. It was not from shame or pain, i was just a intense emotional release. When I came out I felt like running away for a second. Rick pulled me into his arms, kissed me, and reassured me. “You were perfect, baby. I’m so proud of you. You’re not a virgin anymore. You gave me something very special tonight.” His words helped me feel cherished instead of overwhelmed. While cuddling, he admitted, “I know you said you didn’t want to kiss… but I figured you didn’t know what you were missing. With my dick inside you, I could do what I wanted. I wanted you to feel the full man-on-boy love.” I’m so glad he did it. It changed everything.
The second round maybe a hour later, and was much rougher. He turned all the lights on bright again. This time i wanted to be on my elbows and knees, head down, ass up. He was happy help. “Fuck, look at that view,” he groaned. “Your ass looks so good framed by that lingerie.” He gripped my hips and ass cheeks hard and fucked me deep and rough, talking very dirty: “Take Daddy’s cock, you little slut… look at you taking it so well. Such a pretty boy pussy.” He grabbed his phone and took a couple pictures to show me how I looked, it was wild seeing the pictures, seeing myself in a pic with his hairy belly at my ass with his dick buried inside me.
He fucked me hard for over ten minutes, then pulled out and came across my ass and crack. He pushed some of his cum back into my open hole with his cock while I moaned “Oh my god…” Then he gathered the rest in his left hand and wiped it on my lips and left cheek. I passed out before he even came back from cleaning up.
The third round was in the middle of the night. The room was dark. I woke up to him fondling me all over while I was half-asleep. It felt surreal — I didn’t know if I was dreaming. Then I felt the coconut oil on my hole again. He put me on my knees, head down, and pushed inside me.
“I couldn’t sleep with a boy like you in my bed,” he growled, “not when I could be feeling your sexy little body…” He thrust in deep, “...or fucking you.”
He fucked me raw in the dark — grunting, possessive, putting real effort into cumming. He filled me one last time, then went to clean up. I passed out again, left messy on the towel.
In the morning I woke up still wearing the ruined lingerie, dried cum on my thighs, ass, stomach, and part of my face cheek. I felt thoroughly used and claimed. Rick was already up and let me rest, he told me good morning and gave me a kiss before inwent to the bathroom to clean myself up. When i came out, showered clean and dressed, Rick asked if I wanted more with a slight chuckle, I was too sore, worn out, and i think he knew it. We kissed deeply one last time before I left, i felt like I really belonged to him.
The entire drive home every bump reminded me I had been fucked three times. The soreness a constant reminder it was all real.
When I got home I was exhausted, sore, and emotionally raw. I just needed to vent, so I opened my computer and started typing everything — trying to save every feeling, every sensation, every moment of the night I stopped being a virgin and became Rick’s prize.
I don’t know what happens next. But I know I’ll never forget it.
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