Taking My First Cherry - Finally

Author's note: These are the tales of my journey from an unhappily married man to a very sexually active single/divorced man. These stories are based on true events and relationships, although the quotes may not be verbatim. All events are generally stated as best as I can recall, with some embellishment or artistic license as needed, especially considering I am writing this 20 years after the events of the first story. But the substance of each story is true.
I wrote these stories in chronological order but didn't title them very well. If you want to read them in order you have to start with "Middle Aged Male Sex Chronicles 01" and follow them by date of publication.
Everyone was over 18 and everything was consensual. Names and places have been changed or "hidden" to protect identities and privacy.
You may see references to other people or events in my stories, seemingly out of context. I've written all my stories as a chronological account of my life after divorce, but each story stands on it's own unless noted as a new part or chapter.
Bryn
If you read the "College Grad" series, you might recall that Ally, my sex student, had a couple friends from home that I had known as long as I had known Ally, and at a picnic one year soon after I started fucking Ally, her friend Bryn gave me some knowing looks, even biting her lip as she looked at me. I had a feeling Ally had told her what we had been up to.
While Ally was MY slut, Bryn was a legit slut, and she looked the part. Her young tits always spilling out, tight, ripped jeans or shorts that showed the outline of her vagina. She was unofficially the town slut.
Or so I thought.
I was out a a local bar one Friday night, watching a game with a friend. He could only stay for a bit, but I hung back, no other plans.
Bryn was waitressing, trying to make some extra money while she pursued a masters degree in mathematics. She was really smart, personable, just enjoyable to be around. She was Ally's age, I guess about 23 or 24. I was 55, so more than twice her age.
Bryn waved to me several times as she would walk by me at the bar, stopping once to say hello. Around 9:30 I saw her come out of the back dressed in regular clothes, her shift over for the night.
She plopped on the empty stool next to me and said, "Buy your girlfriend's friend a drink?"
I laughed and responded, "Not sure what you mean, I don't have a girlfriend."
"It's OK," she said. "Ally told me, but I'm the only one she told. Your secret is safe with me."
"Do you realize how dead I would be if this got out, and got back to her dad. Deader than dead." I warned. "So please, don't tell a soul OK?"
"What's it worth to you?" she asked.
Was this little bitch blackmailing me? I was getting pissed, and worried.
"Let me ask you, what's it worth to YOU?"
"Well played," she laughed. "Seriously though, I was wondering, would you be willing to, you know, help me the same way you helped her?"
I was shocked. Of anyone who I would have guess needed a sex education, it wouldn't have been Bryn.
"No offense Bryn, but from what I understand, you've had your fair share of boyfriends over the years. I've seen lots of pictures on social media of you with plenty of guys, so I guess I'm a little confused."
"Yeah I know," she said. "Everyone thinks I'm a slut. I dress slutty and I'm always with guys. Truth is, I'm more of a tease than a slut. I've kissed a ton of of guys, and had my tits played with and pussy fingered alot, and given a few handjobs, but that's it. I'd always get scared to go further than that."
"But you wouldn't be scared with me?? I'm 30 years older than you."
"I guess that's the point. Guys my age are so anxious to just stick it in you, you know? Ally said you really take your time and there's no stress or pressure."
"So, are you saying, your a virgin?"
"Yep, go figure. A 23 year old virgin, made it through college with my cherry. As a math nerd, I'd say - what are the odds of that?"
This was interesting. I had never slept with a virgin. My first time was with a local slut way back in the day.
And now, an opportunity to deflower a 23 year old, in my mid-50's. I''d already played with fire with Ally, and I didn't even know Bryn's family, so there was little reason to reject this beauty. Still, I gave her one more chance to change her mind.
I replied, "Almost as long as the odds of a 55 year old being asked to take the cherry of a 23 year old virgin. Shouldn't you just save yourself for marriage at this point, or at least someone you love?"
Bryn rolled her eyes.
"Seriously?" she said. "What is this, 1950? How many people do you know that are virgins when they get married? Plus, I want to know what I'm doing. I don't want to meet a guy with experience and I'm clueless. And it's not like I have a boyfriend at the moment and am gonna fuck around on him like Ally the Ho!"
I laughed, "Ouch!" I said. "Low blow!"
"So what do you think?" she followed up. "Are you afraid I'll gaziantep escort be too much for you?"
She stood as she said this and ran her hand down her body.
This was funny because Bryn was little more than a pixie, standing I'd guess no more than five feet tall. She couldn't have weighed more than 110 pounds, probably less. She had to give up all of her sports in high school because she was just too small.
I stood as well, a good foot plus taller than her, and looked her in the eyes, a serious look on my face, and said, "If we do this, we're goin' all the way. I won't be teased. I'm not into having my time wasted. And we'll do it my way. You got that?"
I saw her shiver a bit, maybe more of a tremble, and she looked up at me and said very quietly, "I understand."
She asked for my number, then texted me her address.
"I work a day shift tomorrow. Can you be there at 8 tomorrow night?" she asked.
"Sure thing, see you then."
I threw money on the bar and turned to leave. She grabbed my arm and turned me back to her, pulling me down and getting up on her tippy toes, barely reaching me to give me a peck on the cheek.
"Thank you," she whispered.
"Thank me tomorrow," I said, and I left her.
************************************************** **********************
Bryn's patents had moved to Arizona upon her college graduation, so she was living on her own in a small townhouse they were renting for her. Very cute and quaint in a little suburb near our town.
I tapped on the door and heard Bryn yell for me to come in. She was in the kitchen in a tight pair of jean shorts and a crop top that barely covered her tits, but nothing else. Her flat stomach and tiny waist were on full display. She was just so damn little. She handed me a glass.
"Ally said you like bourbon," she said as she handed me a glass full.
"I do, thanks," I answered, and grabbed a seat.
I took a sip and looked at her.
"What else did she tell you?"
I could tell she was nervous, and why wouldn't she be. It was all fun and flirty in the bar the night before, but here I was in her kitchen, alone with her, having been invited over to take her virginity. But she was a very confident person so she was carrying the nerves well.
"Honestly? She said you are an amazing kisser, you have a magic tongue and a huge cock and know how to use it, and you come like a fire hose. Oh, and she said I'll be walking funny for a week."
"Oh?" I said, surprised. "So you told her that this was happening?"
"I didn't have to, it was her idea!"
I guess that explains the random text from Ally earlier that day saying - thinking of you, hope you have a great day!
Bryn continued, "She said she wishes she was here so she could watch."
Oh she'd do more than watch, I thought to myself.
Bryn walked over to me and leaned down to kiss me, opening her mouth and offering me her young tongue. We kissed for a good minute, and I could feel her squirming and hear her moaning as our kiss progressed. She sat down on my lap, giving my hand more access to her tiny body.
"I outweigh you by more than 100 pounds I'll bet." I said to her.
"I'm 4'10", 105," she said. "You?"
"Six two, 230." I answered.
She leaned down and licked my ear with her tongue, and whispered, "Take me. Dominate me. Own me."
I stood up, easily holding her with one arm and carried her to her bedroom. I set her down on her feet and stood next to her bed, then reached out to undo the tight top that covered her breasts. It fell to the floor, her perky young tits and tiny pink nipples standing firm.
I sat on the bed and fondled her tits, and asked, "How many boys have played with these titties?"
"About 20," she answered.
I leaned forward and licked a nipple, then ran my unshaven face on them, scratching her lightly and causing her to squirm.
"How many have done that?"
"None, just you. Oh God that feels so good."
I stood. "Undress me," I ordered.
Bryn complied, pulling my shirt off over my head and running her hand through the light hair on my chest. I put my hand on her shoulder and gently pushed down, signaling to her that I wanted her to drop to her knees. She complied with this as well, and found herself face to face with my crotch.
I had no belt on, so it was easy enough for her to unsnap my shorts and lower the zipper, and then pull my shorts down and off, leaving*her face to face with a large bulge in my underwear, and she ran her fingers over the form of my cock through my briefs. I heard her gasp as my cock grew to its full length and the head of my cock began peeking out of the top of the waistband.
"Do it," I said.
Bryn pulled the waistband over my cock and lowered my underwear down and off, never taking her eyes*off of the area between my legs in the process.* She reached with her left hand and grabbed my cock around mid shaft, unable to get her whole tiny hand around it.
"Holy shit," she said as she slowly pumped it.
"How many dicks have you had in your hand?" I asked.
"About ten," she replied.*
"Have you sucked any of them?"
"Two."*
"Did any of these guys come?"
"Not the two that I sucked. I made four guys come with my hand."
"Tell me about that."
"With two of the guys, we were in a car, making out, they played with my tits, one fingered me. I pulled out his cock and he shot his load in about 5 seconds. The other guy took about ten seconds.* Two other guys were at parties in college. Same type of thing. They fingered me and wanted to fuck me. I said no, but I'd give*them a hand job. They came quick too, one in my hand and one all over himself."
Was it a lot of cum, any of them?"
"Not really, one guy was clearly more than the other three, but I wouldn't say it was like a crazy amount. About what I expected."
"How big was the biggest dick you've had in your hand?"
"I didn't measure any of them, one guy said he was seven inches. Yours is bigger I think, definitely thicker. I'm starting to get scared."
"Are you wet?"
"I'm sure I am. If you touched me I'd come in a second."
"Suck me, use your tongue, your lips, and take as much as you can into your mouth."
Bryn did as instructed, licking the crown of my cock, running her tongue up and down the length of my shaft, kissing the head, sucking and licking my balls. For having almost no experience, she was doing great. When she finally opened her mouth to take me in, I was afraid she'd break her jaw. Her mouth was so little, like the rest of her. She did her best though, looking up at me for approval as she struggled to take even the first quarter of my dick into her little mouth.*
I ran my fingers against her cheek and she sucked me, and said, "You want me to own you huh? Oh I will. I'm gonna own your mouth, your throat, your pussy and your ass before it's all over."
I heard her groan with excitement and probably a little fear too, and I grabbed the back of her head and lightly pushed her head forward and more of my cock into her mouth. Only a quarter of the way in and I was already against the entrance of her throat, her lips and jaws stretched wide, her eyes wide to match. I considered some violent deep throat training as I had done to some others, but decided that*Bryn needed a different approach. Oh she'd get her training, but it would be a bit different than in the past with others.
I was anxious to take this girl's cherry, so after a minute or so I said, "I'm going to fuck you now. Stand up," I ordered.
As she did, I unbuttoned and unzipped her jean shorts, then picked her up easily and tossed her onto the bed, grabbing her shorts and pulling them off as she flew through the air. She landed on her back with a bounce, her head hitting the pillow and her legs*automatically opening. She was breathing heavily, almost panting, a combination of nervousness, fear and horniness.
I moved between her legs and got my face down to inspect her pussy.* Like Ally's before, it was flawless. At 23, she was shaved clean, no pimples, wrinkles or stray hair, just a perfect wet pussy, swollen and ripe and ready to be taken.
I took a long lick, starting*at the bottom of her opening and ending at her clit, and when I hit her clit, she grabbed my head and shouted, "Oh God, I'm coming!"
I sucked on her clit and prolonged her orgasm, and she held on tight while she fought through it.
As she came down, I released her clit and continued with some light licking. When she was fully down, I slowly stroked the outside of her cunt with my index finger.*
"How many people have licked your pussy?" I asked.
Her answer surprised me.
"Two," she said.
I had assumed that no one had gotten that far given her prior admissions about her limited experience with boys. She had said a couple guys fingered her but when they wanted to fuck she said no. So I pressed her.
"Tell me about that. Who?"
"Ally," she said. "And my college graduate advisor, Julia."
Stunned!* I knew Ally was horny but I had no idea she'd ever gotten with a girl. I suppose I'd never asked.
"Is Julia a lesbian?"
"Yes."
"I know Ally's not. Are you?"
"God no, I love guys. Me and Ally was when we got high one summer years ago, we licked each other just to see what it was like. And Julia kind of took advantage of me senior year as we were studying for my final. She got me tipsy and convinced me to sit on her face."
"Did you come either time?"
"No, this was the first time that anyone else has made me come. I can do it myself, but no one else has ever given me an orgasm."
Slowly I inserted my middle finger into her. She was tight. A 105 pound*virgin is probably going to be, and she was. I added my index finger, and sure enough I could feel the ring of her hymen as my fingers reached the second knuckle. I moved them in and out slowly, carefully so as to avoid breaking it with my fingers and ruin the moment. I teased her clit with my tongue again as I thrust my digits in and out of her. She was running her fingers through my hair, and I could feel her moving her hips faster and faster as we went.
"I'm going to come again," she announced, and I kept my pace. Faster and faster she went and finally pulled my face into her again as she released with a loud groan.
My face was drenched, my light goatee serving as a sponge for her delicious juices.* A "flavor saver " we used to call it.*
I looked up at Bryn, her eyes closed and head back on the*pillow. She sensed me looking at her and raised her head to look at me, watching as I rose up and positioned myself between her legs. My cock had to be as hard and big as it had ever been, or maybe it's because*it was poised over the smallest pussy I've ever seen that made it look that way.
I understood in that moment why women are nervous as they are about to get fucked for the first time. I was nervous for her.*
Holding my cock in my hand, I worked the tip up and down her slit a few times, alternating between watching and looking at her. Slowly I put the head inside her.
"It's going to hurt," I said.
"I know, but just for a few seconds. I've talked to friends and read all about this, I'm ready. Please fuck me, I'm ready any time, do it."
I was up against her cherry, but rather than push*through from that position, I pulled back til the head was just*outside of her, then thrust back in with some force, breaking through her hymen and burying about three quarters into her.
Bryn screamed like the devil, probably half from her hymen breaking, and the other half*just from the pain of something*so much bigger entering her*vaginal canal. I've had grown women, mothers, yell out when I thrust into them like this, so for Bryn it must have felt like aliens invading.
I held still for a second, allowing a few moments to pass for the pain to calm down, then moved out and back in, a little bit more each time. I looked down and could see some blood on my cock - not much*but clearly present - and it drove me on. Knowing I had deflowered this young tight pixie made me wild.*
Bryn dug her nails into my back and. looked at*me and said, "Oh my God, it hurts so bad and so good. Please just fuck me and don't stop until you come. I'm on the pill, fuck me and come inside of me."
By now I was all the way inside*of her. I sat back on my knees and watched as I plowed in and out of her. I could see my cockhead form a small bump around her belly button as my cock reached its full depth inside of her. I hooked her knees behind my elbows and leaned forward, her tiny body being swallowed by my much*larger form. Anyone watching from the doorway might not even see her, she was that small under me.
*
"Who owns this little pussy now?" I said. "Tell me, who owns your pussy?"
"You do, you own my pussy, it's yours now. Fuck me whenever you want, however you want. All day and night." She was babbling*almost incoherently as I brutalized*her.
Being as tight as she was, there was no way I could hold out much longer.
"I'm coming," I said, and she dug her nails*deeper into my skin as I pumped my load into her. Cum was being squeezed out around my cock as fast as I was pumping it in, there was just no place for all of it to go.
When I was spent, I sat back and was barely able to reach my shorts on the floor. Grabbing my phone out of pocket, I started a video as I slowly pulled my cock out of her. It took some effort because she was so tight, but eventually my dick fell out, a river of cum and blood flowing out behind it, down into the crack of her ass and soaking the bed cover.
"Let me see," she asked, and I showed her the video.
"Oh my God, that is so fucking hot. How the hell did you fit that thing inside of me?"
"Well, God made you to be able to push a baby out of there, and my dick is smaller than a baby."
"Not by much," she laughed.
We laid in silence for a few minutes, her basking in the glow of losing her virginity, and me the same.
"Any regrets?" I asked.
"None whatsoever. Only that I didn't get to properly suck your dick earlier," she answered.
"Well," I said, "unless you're kicking me out, there's plenty of time for that and more if you want."
"Oh, I want," she said. "Can you stay the night?"
"Yes," I replied. I had packed a bag just in case. Years of experience.
Wait here, let me run into the bathroom quick."
Bryn excused herself to go to the bathroom and jump in the shower.
"OMG!" I heard her yell from the bathroom. "How much cum did you put up in me?"
she asked. "It's still coming out!"
I chuckled as I ran to my car for my overnight bag.
Bryn opened the door to the bathroom and called me in with a crooked finger, having me step into her very small shower while she squeezed in with me, and very lovingly rinsed the blood and residual cum from my cock.
We left the bathroom and stripped the blanket off the bed, putting on a fresh one and then climbed into the bed.
Bryn got down between my legs and said, "I want to make you come with my mouth. Do whatever you have to do. Own my mouth like you own my pussy."