College Grad Seeks A Sex Mentor 02

Big Tits

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.


Ally, Part 2

Ally was back late the next afternoon, as planned, to continue the “lessons.”

I poured her a drink and we talked a bit, me first wanting to make sure that she didn’t have any regrets or that she didn’t feel like I had somehow taken advantage of her. Last thing I needed was her dad at my door with a shotgun and my name all over the news. She assured me that all was fine and she was anxious to continue.

So, we talked a little about sex before we got to business. She wanted to know about blowjobs.

“Well,” I said, “first thing is, there’s blowjobs, and then there’s going down on a guy, or giving head. There’s a difference. A proper ‘blowjob’ implies that it was done to completion. The girl makes the guy come with her mouth. If it’s oral sex as foreplay to regular sex, then you don’t call it a blowjob. At last I don’t. Make sense?”

“Yep, I get it,” she said with understanding. “So really then, I’ve given head, but have never given a blowjob, since no guy has ever come in my mouth. Is that what you’re saying?”

“That’s right,” I confirmed. “Now, have you tried to go all the way and couldn’t get the guy to come, or you always stopped intentionally as a warm up to sex?”

“Mostly I stopped so we could have sex, but I haven’t been able to get my boyfriend to come when I tried.”

“OK. Think about it this way. Nature intended us to procreate by having a penis come inside a vagina. The mouth was never part of the deal, so really it’s unnatural. So to make a guy come, you have to make it feel like he’s fucking a vagina. You have to stimulate the whole penis, just like when a dick is having sex, the whole thing goes in and out, not just the head. So if you can’t take the whole thing in your mouth and throat, then you have to use your hands too.”

I continued: “But, whether you are going for the orgasm or just using oral as foreplay, some basic rules apply. For one, guys love to watch, so try to be in a position where he can see your face and see his dick going into your mouth. And when possible, lots of eye contact. We love eye contact during oral.”

She jumped in, “That works both ways. When you looked at me yesterday when you were eating my pussy, it was crazy hot. And putting your fingers in my mouth with my juice all over them, that was so damn sexy. I never thought about tasting my own pussy.”

“I’m glad you liked it,” I said. “Your pussy is delicious.”

I continued. “If you are going for the orgasm, you don’t have to go right for the kill. Take your time, explore. Lick around the head, run your tongue and your lips along the front, sides and back of the shaft. Go low and lick his balls and take them into your mouth. Gently though, that’s a sensitive area.”

“Any questions, or should we just go back to my bedroom and work on it as we go?”

She smiled, and said, “I thought you’d never ask!”

We walked back hand in hand, her saying, “I can’t wait to get your dick in my mouth.”

I stopped her and said, “That’s good, dirty talk is always a turn on. No need to go crazy with it, but don’t be shy. Nothing worse than quiet sex.”

We got to my room and I sat on the edge of the bed, pulling her over to me and kissing her, then gently pushing her to her knees. She unbuttoned my shorts while I stripped my shirt off, then she moved to start taking off her top.

“Leave your clothes on for now,” I said. “A fully clothed woman giving head to a naked guy is a real turn on. Guys love submissiveness in women, sexually, at least some of the time, and being on your knees fully clothed is a super turn on.”

Ally was an eager and willing student. Once she had an idea of what guys liked, she was a natural. She licked the length of my cock, swirled her tongue around the head, ran her pursed lips up and down, played with the rim, licked and sucked my balls, all while watching me watch Ümraniye Escort her. She dipped her finger into my precum and sucked it into her mouth, commenting again how salty it was and how much she liked it.

I offered instruction only occasionally, such as every few minutes, take the whole cock into her mouth as deep as she could and use her hand in unison, making sure to keep everything well lubricated. She only took my dick in her mouth to the entrance of her throat, and I figured I’d save deep throating lessons for another day.

“Tell me what you’re thinking,” I said.

“Your cock is so big and tastes so good. I love sucking you. I love your precum. I want your cum so bad.”

“Very good,” I commended her.

After about 15 minutes of playing, I told her she should now focus on making me come by putting as much of my cock into her mouth as she could, using her hand, and making it as tight as possible to simulate a vagina. I instructed that she could look away on occasion, but as soon as I announced that I was going to come, she should lock eyes with me again. Making eye contact while you are coming into a girl’s mouth is the height of all sexual submission, in my opinion.

It felt so good, and it wasn’t long until I announced, “Ally, don’t stop, I’m going to come soon. It will be alot of cum. You’ll feel me harden and grow slightly about five seconds before the cum starts to flow. You might not like the taste so be prepared. Try not to gag or spit, but it’s OK if you do.”

She was looking at me as I spoke to her, and it was so wonderful, and I told her, “Keep going, just like that baby, you suck my cock so good.”

She took my dick out of her mouth long enough to look at me and say, “I want your cum so bad, please come in my mouth.”

That was all it took. I pushed her mouth back onto my dick and roared to an orgasm that shook the walls. I held her head steady but not so forcefully that she couldn’t pull away if she wanted to, and I made sure not to go too deep, minimizing the risk that she’d gag and choke. But she didn’t flinch. We looked at each other while she took my cum into her mouth and I watched her swallow as it flowed. It was an incredible sight and feeling.

She held me in her mouth until she was sure I was done and started getting soft. My cock fell from her mouth, but she grabbed it and milked another drop out like I had showed her with the precum the day before. A natural cum slut.

I offered her my hand to help her up, and she plopped on the bed next to me. I looked at her and quizzed, “Well, what do you think?”

She replied, “I’m asking you the same, what did YOU think?”

I laughed and said, “Well let’s see, I got a great blowjob from a beautiful young lady, came in her mouth, and she’s sitting on my bed next to me, so I guess all in all its A plus, 100%, grand slam home run!!”

She smiled and said, “Oh good, I’m so glad. I wasn’t sure if I was doing it right.”

“Well, you have a great coach,” I joked. “How was the taste?”

“Different than the pre-cum, sweeter.”

“That’s interesting,” I said. “I’ve always heard that a man’s diet affects his cum taste, and I had a feeling that we’d be doing this today, so this morning I had fruit for breakfast, then a light lunch and a glass of pineapple juice.”

“Yes!” she exclaimed. “Pineapple! That’s what I tasted. That’s so funny.”

“I’ll get a case of it then,” I joked.

I leaned toward her and said, “Gimme a taste” and I kissed her deeply.

The kissing continued, and she started to squirm. I started to feel her body with my hands, and one hand snaked between her legs and grabbed her pussy.

She was ready for more, and asked, “Can guys do it more than once in a day?”

“Do what?” I kidded.

“You know, get hard and come. You just came, so will you be able to do it again today?”

Time for another lesson.

“Ally, at my age, it usually takes about 20-30 minutes for me to be able to get hard again. In my case, a lot depends on the time of day, my diet and overall health, stress level etc. But on average I’m about 20-30 minutes. Guys your age should probably take less than that but it’s different for everyone.”

“Got it,” she said. “So then, what are we supposed to do for the next 20 minutes?”

I said, “Well first, tell me what else you have questions about. I need to know what you need to know.”

“Well, basically everything. The only position I’ve ever had sex in was what we did last night, although the legs on your shoulders thing was new. My friends talk about doggy style, and obviously I know what it is, I’ve just never done it. So really I want to learn all the positions and stuff. I’m not moving until the fall, so we have all summer.”

This would be one summer to remember for sure.

I sat back on my bed in a sitting position against my pillows, feet straight out, and told her, “Stand up and slowly take your clothes off. You don’t need to dance around like a stripper. That’s for the movies. Guys are very visual, İstanbul Escort remember that, so watching you undress is a great turn on.”

She did as instructed, slowly peeling off her top, her young, perfect braless tits bouncing into view, and pulled off her jeans. Her tiny thong was last.

“Come over here and sit by my feet, facing me,” I ordered.

She assumed the position I directed, and I told her, “Open your legs. Touch yourself. Don’t come, just play with yourself the way you described to me yesterday.”

She did exactly as instructed, first diddling her clit a little, then inserting a finger into herself, wiggling it around and then moving it in and out.

“Two fingers,” I said, and she complied, her eyes fluttering as she penetrated herself. She was moving faster and faster now, and I could sense a build-up, but I didn’t want her to come.

“Slow down. Take your fingers out and taste yourself.”

She stuck her fingers in her mouth and let out an audible “mmmm.”

“More,” I commanded, and she resumed finger fucking herself.

“I want a taste,” I said, and her fingers found their way to my mouth.

“Again, but this time rub your pussy juice on your nipples.”

“Oh God,” she said, and I could tell she was as turned on as she’s ever been. No doubt this was the first time she had masturbated in front of anyone.

Meanwhile, my cock was starting to stir, slowly growing as I watched this fox masturbate for me.

I wanted to taste her some more, so I said, “Come up here and sit your pussy right on my mouth. Sit down and grind on me as hard as you want to, don’t worry, you will not suffocate me, I like to be smothered. I don’t know if all guys do but I do. Sometimes guys like to be in total control, and other times they like to have the woman be in charge. So for right now, you are in charge, so have your way with me.”

A little grin crossed her face, and she had no questions. She stood up on the bed and walked herself up toward my head, then squatted down and planted that fresh pussy right on my mouth. I grabbed her thighs and pulled her down hard, and she took over from there, rubbing herself up and down, my unshaven face scratching her sensitive shaved pussy lips and causing all sorts of sounds to escape her mouth.

Her muscular thighs were on either side of my head, clamping me in a vice-like grip while her pussy absolutely dominated my head, mouth and face. God I love this like nothing else, and she was taking to it like a fish to water. I could barely hear her muffled cries and orgasmic vulgarities since my ears were clamped shut by her thighs. I had my hands on her ass and was holding her down on me, and I thought I’d died and gone to heaven.

After 10 or 15 minutes of this, she finally eased up and relaxed her body. I pushed her off slightly so I could look at her. She had given me exactly what I wanted and needed, and she knew it from the wet, exhausted look on my red face.

I said, “Ally, my cock is hard for you again, slide down and put it inside your pussy and ride me.”

She reached back and felt my dick, hard as steel once again in her hand. I guess she took to being “in charge” very well, because she ignored my instruction and instead spun around, planted her pussy back on my face, and leaned forward to take my cock in her mouth in a 69.

OK, I thought, I guess we’re not done with the foreplay. I went back and her pussy with a vengeance, spreading her ass cheeks with my hands and opening her up. I buried my face into this young pussy and wedged my nose in her ass. She was sucking me at the same time, while she moaned and squealed with delight at the things I was doing to her. I strained my neck to get closer to her asshole, and flicked my tongue against her little rosebud, and she inhaled my cock deeply when I did that.

I needed to fuck her now, so I took control.

Swinging her legs to the side, I said, “Now, get up and ride me.”

Ally swung her body around and laid on top of me.

She said, “I’ve never done it this way.”

“I know,” I said, “but believe me, it’s easy and will come naturally. Just reach underneath us and put the tip of my dick at the opening of your pussy, then slide back on it. You can go slow, or take it all in one thrust. You’ll love it, trust me.”

She did as I told her, and she slowly sank back on my dick. It felt like a velvet glove sliding onto my cock.

She groaned as I bottomed out, and leaned down to kiss me, whispering in my ear, “Oh my God, it feels so good.”

I grabbed her luscious ass cheeks and squeezed them, then started coaxing her to work her pussy up and down.

She said, “My pussy is a little sore from yesterday but it’s feeling better already.”

“Take your time,” I said. “I’m in no rush.”

She did, thrusting slowly, maneuvering herself to get different angles every minute or so. I kissed, sucked, licked and nibbled on her nipples, and she had several orgasms as we changed angles, depths and speeds. At one point I reached Anadolu Yakası Escort beyond her ass cheeks and tickled her asshole with my finger, which triggered yet another orgasm. This girl was having more orgasms than anyone I could remember. Ah to be young again, I thought.

Finally I grabbed her hands and pushed her up into a sitting position, one of my favorites. She grimaced when she got to a fully upright position.

I asked, “You ok?”

“For sure,” she said. “You’re just so deep like this. Give me a sec to adjust.”

So she sat there for a minute, just kind of wiggling her hips to get comfortable, and we started to talk again.

She said, “You like touching me back there, don’t you? My ass I mean. You’ve licked me there and put your finger there. Is that normal for guys or is that kind of hit or miss?”

I laughed and said, “Probably hit or miss. I suspect most guys are OK fingering a girl’s ass, but licking and anal sex is probably 50-50 I’d guess. To each his own. Do you like it?”

“Oh yeah it feels great. I just need to know if all guys are into it.”

“No, probably not all guys. But if you aren’t, no one should pressure you. I’ve had women tell me her ass is off limits, and I respect that, and you should feel free to say the same to me or anyone.”

“Well,” she said, “I don’t know what I’m into until I try it. So far so good. So, you can do whatever you want to me.”

Music to my ears.

I asked, “How many times have you come?”

“Oh God at least four or five. I can come a lot, there have been times when I lay in bed in the morning and come 10 times in like an hour. Maybe I’m just a horny slut?”

“Maybe,” I agreed. “Nothing wrong with that. Just like with everything else that we love – everything in moderation.”

She had adjusted to the depth as we talked, and was slowly rocking and grinding while sitting up straight on me. What a sight to behold. I squeezed her tits and used my thumbs to toy with her nipples a bit.

I showed her the baseball catcher squat position, and that was it for both of us. Putting my hands under her ass to support her while she bounced up and down, we hit a rhythm that sent us both over the edge.

“I’m going to come baby,” I said. “Keep going.”

She kept her pace and said, “Yes, do it. I want to feel it.”

On a down stroke I grabbed her and held her down tight and came inside her once again. She was sweaty and out of breath and was as sexy as anyone I’d ever seen.

Ally collapsed on top of me and we laid there for a few minutes. The next thing you know I woke up and it was midnight.

I nudged her and said “Ally, you better get home.”

“It’s fine”, she said. “I told mom I was staying at Daphne’s tonight. Tomorrow is Memorial Day so I don’t work. We can sleep in.”

I woke I up about 5:30, the usual for me. Ally was naked in bed next to me, breathing quietly. I started lightly running my fingertips over her stomach, chest and tits, her nipples getting hard as she squirmed and started to wake up. My fingers went to her pussy, which got wet under my touch. I think she was only half awake when I mounted her and began a slow, steady rhythm. She was wide awake and clawing gently at my back as I steadily thrusted into her and came inside her. No words were spoken, it was a gentle loving fuck that sent her back to sleep.

I went out to the kitchen and had my coffee and went through my normal routine. At her age I knew she’d sleep late, so I let her. Around 10:00 I heard some noise, so I went back to the bedroom to find her awake.

“Coffee dear?” I asked with a laugh.

“Sure! Cream and sugar please. Regular cream I mean,” she joked.

We shared a coffee in bed and chatted a bit, she said she slept like a rock from all the orgasms.

She asked, “So Professor, what was the teachable moment this morning? Or were we just fucking for the heck of it?”

“Well,” I was searching for an answer. “That’s your teachable moment right there. Sometimes sex is done just for the heck of it, without words or bells and whistles. Just two people enjoying each other.”

“Nice try,” she chided. “I’m just having fun with you. I told you, do whatever you want to me. I was just surprised it was so early.”

“So that is a good lesson then. Guys love sex in the morning, our testosterone levels are highest when we wake up.”

“Good to know. So, now what?” she asked.

“How about a shower?”

“YES!!”  She practically jumped out of the bed. “Give me a couple minutes in the bathroom then come on in when you hear the shower running. Do you have an extra toothbrush?”

“Yep,” I answered, “In the cabinet are a couple, see you soon.”

I went out to the guest bath to brush my own teeth and to give her a bit of privacy, then went into the bathroom after hearing the shower run for a minute. In the bathroom I found a soapy 22 year old wet dream come true, I slipped my shorts off and joined her under the spray, and she greeted me with a kiss and a soapy hand for my already half hard dick.

She stroked my shaft and balls and said, “Do you have more cum for me?”

“Baby, I have all the cum you want,” I promised her.

We took a few minutes to wash our hair, and wash each other’s bodies thoroughly, then she dropped to her knees in front of me.

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