College Grad Seeks A Sex Mentor 03

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 3
I didn't see Ally at all the week following the Memorial Day picnic, but I did have fun with Jennifer and Susan: Jennifer solo on Tuesday, and the two of them together on Friday. Our three way relationship had been going strong for about nine months to this point (see "Soccer Moms' stories).
I fucked Jennifer twice that Tuesday, the second time from behind on my bed, her face in my pillow.
When we were done, she opened her hand and showed me an earring in her palm.
With a grin, she said, "This was under your pillow. I'd assume it belongs to Susan, but it doesn't look like the normal expensive stuff she usually wears."
I didn't know what to say, but obviously couldn't give away the Ally thing to anyone, so I just said, "Yeah, must be. Or maybe it belongs to my daughter, she watches movies in here sometimes."
"Be careful," was all she said. I had a feeling that her sixth sense was working overtime and that she had figured it out.
No big deal, I was obviously free to play around, I think she was just worried about how it could end if me and Ally were ever found out.
Ally was at the beach the following weekend, and we arranged for her to come on Sunday evening after she got home. My instructions were for her to get a light sunburn wearing a bikini, since I have a little fetish for tan/burn lines.
Sunday afternoon she sent me a picture of herself, naked from behind, her glorious body marked by some wonderful burn lines on her ass and across her back from her bikini top. The middle section of her ass was nice and white, in contrast to the bottom of her ass cheeks and thighs which were noticeably red, though not severely.
She messaged the pic with, "You should see the front!"
"Ouch!" I responded. "You did that for me?"
"Of course. Anything for you. But, I might need you to rub some lotion on me so that my skin doesn't dry out."
I sent her a picture of some aloe lotion and said, "One step ahead of you."
She appeared at my door around 6:30, and I had some dinner waiting for her. We ate and moved to the living room, where she told me about her weekend, hanging with friends and getting hit on in bars.
"Are you trying to make me jealous?" I asked.
"Are you?" she asked in reply.
"Not at all," I lied. "You're young and hot, I'll bet you were very popular at the beach. Did you hook up?"
"Nah," she replied. "Technically I'm still dating Chuck. But given what I do here, and what I'm gonna do in about ten minutes, it's kind of a gray area as far as my loyalty to him. But really I had no interest. I just wanted to get back here and get fucked by you."
Ally was wearing Adana Escort a beach cover up, and she stood up and lifted it over her head, leaving her standing before me in her yellow bikini. She reached back and unsnapped her top, letting it fall to the floor and exposing her white tits and delicious looking burn lines around them. I almost came just looking at her.
Ally hooked her thumbs in the waistband of the bottoms and slid them down her legs, standing upright to show me the white skin around her pussy, then turning around to give me an in person look at her ass and the lines that were there.
I groaned and reached for her.
"Not yet," she said. "I'm skanky from the beach. I'm gonna go shower. Meet me in the bedroom with the lotion in ten minutes."
OK, I guess Ally is calling the shots now.
I was sitting in my bedroom chair when Ally came out of the shower, wrapped in a towel, still wet, her hair in a bun so it wouldn't get wet in the shower..
As she walked toward me, she said, "Get your clothes off."
I quickly stripped out of my shorts and t-shirt, and she dropped to her knees in front of me.
"I've been thinking about this big dick all week. I wanted to suck it at the picnic last week in front of everyone. All I could think about while we were all talking was how good it felt fucking me from behind that morning, and I couldn't wait to get it inside me again. Waiting a whole week was fucking torture."
Ally played with my cock and balls, swirling the precum around the head and licking it, then proceeded to give me some A oral sex. The lessons I had taught her the prior weekend had paid off, and she was sucking my cock and balls like she had been doing it her whole life.
At one point she slowly, agonizingly slowly, took my whole cock into her throat, all while staring at me, until her nose was pressed against my stomach. I grabbed her by the head and held her there, thrusting my hips forward to get even deeper. She gagged a bit, but held on without convulsing too badly.
I slowly fucked her throat for a few minutes, but as the minutes went by I could feel myself getting close, and Ally's eyes met mine as she heard my breath quickening.
She took my cock out of her mouth and looked at me, saying, "Come on me. On my face and tits, please. I want your cum so bad."
I stood up and stood over her, and she shed the towel from around her body. Her hair was back in a bun so it didn't get wet in the shower, and her young freckled face made an appealing target. I took my cock in my hands and stroked it a few times, pointed it right at her face and warned her that I was about to come.
The first shot hit her right in the forehead, the next two on the side of her nose and cheek, then I pointed down and finished on her chest and tits. She knelt back so that the cum on her face dripped off of her chin and onto her chest. I looked at her and her eyes were closed, and she was making a bit of a face. Not a pleasant one.
I stepped backed and looked at her, and started laughing.
"You OK," I asked.
I watched her blindly search for her towel on the floor and wipe her face off. She opened her eyes and looked at me and returned my laugh.
"I think I liked the idea of cum on my face more than I liked the reality. It wasn't awful, and on my tits is fine, but I think I'd just prefer it in my mouth."
"Hey I don't blame you," I replied, thinking about the time Jennifer and Susan made me come on my own face a few months prior (see "Soccer Mom" series, Week 5). But at least now you know."
"True," she said. "If a guy ever wants to do it, and I'm really into him, I'll let him, but I guess it's not really my thing. I'd rather Adana Escort Bayan taste that sweet cum on my tongue."
Ally threw on my robe (I noticed her take a quick sniff of it when she put it on -- Susan had worn it two days earlier after a group fuck with Jennifer), and flopped on the bed. I put my shorts back on and grabbed us each a glass of wine, and we sat on the bed chatting for a few minutes.
After a time I went to the bathroom and grabbed the bottle of aloe. Returning to the bed, I slipped the robe off of her shoulders and had her lie on her back. Her front wasn't as red as her back, but she needed some attention anyway. I squirted some lotion in my hands and rubbed my hands together to warm it up, then started on her stomach, working my way down past her belly button, then up to the bottom of her young tits.
Her chest was rising and falling as I rubbed her, and when I cupped and squeezed her tits together with both hands, she let out an audible groan.
Slipping my shorts off, I straddled her chest, pushed her tits together and started tit fucking her. She didn't have the biggest tits, not ideal for tit fucking, but the lotion and the sunburn were a turn on and I loved seeing the contrast of my naturally darker-skinned cock against her red and white skin.
Ally opened her mouth occasionally and licked the tip of my cock when it poked through her tits, and after a few minutes I moved up over her and dropped my balls in her mouth in a classic tea bag. This turned her on and she grabbed my ass and pulled me down, getting my whole ball sack into her mouth.
If I hadn't just come on her face, I might have done it now, but I had other ideas.
I pulled my balls out of her mouth, and she whimpered, reaching out and grabbing my cock and pulling me back to her. I let her suck the tip again for another minute and get some pre-cum on her tongue.
"Roll over," I commanded, and she flipped herself over onto her stomach, her hips raised slightly off the bed. I could see that she had reached one hand back between her legs and was lightly fingering herself.
"Keep touching yourself, but don't come."
I lathered up my hands again, rubbing aloe onto her burnt upper back around the strap lines, then down to her lower back. Skipping over her ass for the moment, I massaged the backs of her muscular legs.
Her round ass was so fine, and as I pushed my hands up from the backs of her legs and got the globes of her ass in my hands, I spread her cheeks a bit with my thumbs and saw her finger in her cunt, and her asshole winking at me, just begging for attention.
I placed one finger next to hers and we fingered her cunt together, and using one of my hands and one of hers, we spread her ass open and I leaned in to tongue her asshole. Ally was beside herself, humping her hips up and down and shoving her ass back at me to get maximum pleasure.
"Fuck me, please," she pleaded, and I couldn't resist her.
I got behind her and placed the head of my cock at her entrance, and told her, "Push back when you're re...."
Before I could finish she pushed back and swallowed my cock with her pussy, letting out a loud groan.
"Oh God that feels so good," she cried as I grabbed her hips and fucked her steadily, massaging her ass as I went, then tickling her asshole with my thumb.
Slowly I pushed my lubed-up thumb into her asshole, and her reaction was immediate.
"Oh my God what are you doing to me? Holy shit!"
"Tell me what a slut you are, " I told her.
"I'm such a slut, I need your cock, I'm your cock slut and your cum slut. Keep fucking me, please."
After a few minutes of this, I pulled my cock out of her pussy and my thumb from Escort Adana her ass, then lined up my cock at her back entrance.
"Do you want to try this?" I asked.
"I do, I want to try everything. Just please go slow."
I grabbed some aloe and massaged her ass some more, sliding my cock between her cheeks and getting my cock nice and slippery.
Placing the head back at her rear entrance, I said, "Go ahead, when you're ready."
As she pushed back, I pushed forward, and the head of my cock popped in past her ring.
"OH GOD!!" she yelled. "Stop!"
I froze, thinking I'd hurt her. Then I realized she was fingering herself again, and she said, "I need to come. Oh God I'm gonna come."
I felt her shake and come, and she pushed back into me further as she did. My cock went about a third of the way in, and we stopped again. She fingered herself to another orgasm, then pushed back some more. This continued for about three more pushes and orgasms, and a few minutes later I was buried all the way in her ass.
Ally was sweaty, I could see the beads of sweat running down her back from the back of her neck. She wasn't lying last week -- she's an orgasm machine. Oh to be so young again.
She looked back at me and said, "I can't believe it fit. I'm never gonna be the same."
I laughed and slowly pulled out a few inches, then slowly back in. We started a rhythm like this, backing out further each time and thrusting back in harder each time, until she had adjusted completely and we were fucking steadily.
Ally had her ass in the air while she rested her torso on her shoulders, her face buried in the pillows and moaning obscenities. I was in the same place, aroused beyond belief, and I could feel the cum boiling in my balls.
I reached forward and grabbed her hair by the top of her scalp and pulled her head back a bit, and said, "I'm going to come in your ass. I knew you were my slut but I didn't know you were such a dirty fucking whore. You want my cum in your ass, you dirty slut?"
"Oh fuck," she said. "I didn't know either. I love being your slut. Fuck my ass and come in me, please, I'll do anything."
"Grab my balls," I said, and she did, just as I released into her.
She squeezed my balls as my cum shot into her, and it was quickly squeezed out of her ass around my cock in a loud wet bubbling sound. I collapsed on top of her and we both laughed, a sweaty cum covered mess.
I wanted her to stay for the night, but she had to head back to her parents, who knew she was home and she had to work in the morning. She cleaned herself up and kissed me goodnight and headed home.
I'll wrap this chapter up by saying that Ally and I did it all, and more, over the next two months, until she packed up and moved a few hundred miles away in mid-August of that year. She wanted to experience every possible aspect of sex, so we used toys, had outdoor sex, experimented with light bondage. We had sex on her period a couple times, and I convinced her that, for me at least, it's not a disgusting turn off.
I fucked her at least once a week, sometimes more, mixing in anal on occasion, and she loved to swallow my cum. I probably came in her mouth as much or more than in her pussy.
We even discussed a three way, which never came to fruition because her college friend that was supposed to fly in for it ended up getting pregnant. Of course that wouldn't have been a problem for me but I didn't push it. I almost asked about her slutty childhood friend, but thought better of that too.
Ally broke up with her boyfriend. I still see (and fuck) her on occasion when she is home to visit. I went to visit her once and fucked her all weekend in between sightseeing in her new city. People looked at us together and probably thought, "What a cute dad and daughter."
I've committed to myself to end it when she or I start dating someone seriously, but for now there's no reason to stop.
Still a few more adventures to go.
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