The girl I've been seeing, Christine

"Staring at this hot ass of yours has me thinking about that girl I told you I've been seeing, Christine. She likes it from behind too." I said to Lucy as I began caressing the two supple globes of her ass that were staring me in the face. "She reminds me of you too, with her friendly, outgoing personality. Her blonde hair isn't as long as yours and she's got brown eyes instead of blue, but she's got a nice, big pair of tits, a thick, round ass like yours, and she's real fun in bed. You want to know what she likes when we're fucking? She likes to take it in more than just one hole." I told her as I started rubbing my thumb around the rim of her anal sphincter then began probing the entrance.

Pornstar: Shirley Harris

Keeping my dick buried inside her pussy, I spit down on her ass to lube up the entrance, then slowly began inserting my thumb until I slipped through her barrier to my first knuckle.

Lucy seemed to like the idea, and the feeling as well, and let out a groan from deep in her throat as she nudged her hips back to meet me, burying both my thumb and my dick deeper inside her holes.

"I guess we found another trait you and Christine share, huh? It looks like you might get off on having both your holes filled up just as much as she does." I told her before spitting down onto her exposed, puckered starfish again then brought my other thumb over to surprise her, trying to slip it in next to the first.

"Holy shit!" she squealed as she felt me attempt to pry her open. "Oh fuck, it's too much!" she yelled out, unable to get herself to relax and accept the additional intrusion. "Shit, shit, shit!"

"You don't want me to stop, do you Lucy? I thought you said I could do anything I wanted to you?" I asked her, not making any attempt at all to stop what I was doing and conveying my disappointment with the tone in my voice . "I sooo wanted to show you what these college whores have me doing to them, but if you can't handle it..." I said, leaving the sentence unfinished.

"No, no, I do want it! Just please give me a second, David!" she begged me breathlessly. "Let me take a deep breath, then when I blow it out, I want you to shove your thumb inside me. I can handle it. I know I can."

If I actually had the presence of mind to think about what was happening at that point, that my friend's mom was not only begging me to stick a second thumb up her ass, but coming up with a plan for a way that she'd be able to tolerate it, I probably would have passed out from shock, but by then, my dick was doing all of my thinking for me and I was now just treating Lucy the same as I would any other slut that wanted to fuck me. "Don't tell me you can handle it, show me." I said, slightly increasing the pressure of my thumb against her constricted opening.

To Lucy's credit, she did exactly what she said she would, taking a deep breath in, then letting it out slowly, and when she did, I felt her asshole open up just enough for me to jam my thumb inside her before she had a chance to react. "Aaaiiiiyyyyeee!" she shrieked as she threw her head back and reflexively tried to pull away from me, obviously unaccustomed to being violated like that, but I curled my thumbs inside, refusing to let her go.

"Just breathe through it Lucy." I told her soothingly as I kept my thumbs in place but started sliding my dick in and out of her again, trying to get her attention back on the pleasure she's been feeling in her pussy instead of the new sensation in her ass. "In, and out... in, and out..." I said, matching my words to the movements of my hips. It took less time than I thought it would for Lucy to start to visibly relax and even less time for her to seem like she was starting to enjoy it, even beginning to let out little whimpers of pleasure. Once I noticed this, I started to slightly increase the pace of my fucking, started moving my thumbs deeper inside her, and spitting down into her now gaping ass, trying to lube up her poop shoot as much as possible to prime her for what I wanted to do to her next.

I decided to give her a little say in the matter this time and started telling her more about Christine. "Ooh Lucy, you're starting to like this, aren't you?" I asked her as her whimpers started turning into moans. "I can feel your pussy getting wetter by the second. Christine's pussy does the same, but you want to know something else about her? My thumbs aren't enough for her. She likes to have her ass stretched even more and the only thing that will satisfy her is if I stuff it full of my dick. Do you know that she loves it so much, she actually begs me for it!? Have you ever begged anyone to fuck your ass before Lucy? Do you have any idea how much of a turn on it is to hear a woman beg you to fuck her ass?! Well that's what I want to hear right now Lucy. I want to hear you beg me to fuck your ass!" I told her with a growl, spearing my thick fuck meat deep within her sheath, letting my primal urges take control.

"Oh god yes! Please David! I want you to fuck my ass! Sodomize me and make me your little anal whore!" she screamed, back under the spell that my dick had seemingly cast on her.

Taking my dick out of her pussy, I spit into her hole one more time before removing my thumbs and quickly lined up my head with her opening. I began pushing into her gaping ass before it had a chance to recover and constrict to it's normal state, letting out a low moan as I nudged past her outer ring and into her bowels.

Grabbing hold of Lucy's hips, I started pushing myself deeper into her anal sheath. I went slowly at first, unsure how well she'd be able to handle it, but with my dick still slick with her pussy juices, I slid in relatively easily and soon had half my length inside her dark tunnel. Not forcing myself any deeper than that for now, I started to work myself in and out of her, keeping my movements small and giving her a chance to accommodate to my member, but just like when my thumbs were in her ass instead, she didn't require much time at all.

"Holy shit, it feels like you're ripping me apart but my pussy is still tingling! I didn't think it would be this good!" she exclaimed. "God, I love how you're filling me up! Ooohhh!... Ooohhh, David!"

She didn't think it would be this good?!? Does that mean she's never had anal before?!? were the thoughts that went through my head as I felt her relax even more and allow me to start increasing my pace. Well of course I had to find out the answers to those questions and immediately asked them of her. "This isn't the first time you've had anal, is it Lucy?" I asked her, doubting that it was the case.

"I've tried to do it before... but it always hurt too much... and I could never relax enough to do it. Unnnhhh!... You're the first one... that's ever been able to... get themselves inside me like this!" she admitted, her sentences broken up into quickly halted phrases as her breathing rapidly became more shallow. "Fuck!"

I was shocked by that statement, nearly positive that someone as easy as she obviously is, must have been fucked up the ass before! The fact that I was the person that truly got to take her anal virginity only excited me even more and I found my pace quickening without realizing it.

Lucy began grunting and groaning in that odd mix of pain and pleasure and I remember telling her how her ass felt even better than Christine's. This compliment seemed to turn her on even more and her moaning became louder as she slowly grew accustomed to me violating her backdoor.

As much as I wanted this moment to last forever, it wasn't long before the simulation from her tight anal passage had my balls tightening and stomach clenching and I knew I wouldn't last much longer. "Oh fuck Lucy, I'm gonna cum soon! Can I do it on your tits?" I asked her, hopeful that she'd fulfill my fantasy and let me unleash my load on the two, soft pillows of flesh that I'd been sneaking looks at for the better part of my pubescent years.

"Yes, do it!" she screamed out through clenched teeth to my absolute delight.

As I rapidly approached the point of no return, I quickly withdrew myself from her rectum then moved to stand over her chest. Lucy flipped over for me without being prompted and even brought her arm across her chest to squeeze her tits together, giving me a more prominent target to aim for as I started rapidly stroking my member, pointing it down towards her chest. "Oh fuck, here it is!" I warned her as I felt my seed boiling in my scrotum and working its way up my shaft, then let out a loud "Uuunngghhhh!!!!" as the first rope of cum blasted out of me, squarely hitting my intended target.

Lucy screamed out encouragement to me, begging me for my seed. "Yes!... Yes!... Oh, that's it David! Cover my big fat titties with your cum! Shoot that thick cream all over me!!" she pleaded as I vigorously pumped my shaft, glazing her magnificent bosom with wave after wave of my creamy white spunk.

To this day, I'm not sure if I've ever cum for as long as I did that morning and I still can't believe the amount of semen I managed to deposit on Lucy, but on that day, I was responsible for a scene that looked like it was taken straight out of a porno. When I finally felt my contractions come to an end and I had milked the last bit of cum to the tip of my dick, wiping it onto her chest, I got the chance to admire the site of Lucy smiling up at me, both tits fully coated with a layer of my glistening, white seed which was already dripping down to form a growing puddle between the two massive globes.

"Wow David, that was one of the top five fucks I've ever had!" she complimented me as she began sitting up on the couch. "It's good to see you're leaning such useful skills at that college of yours." she said giggling as I sat next to her on the couch, spent, with my rapidly softening dick flopping down between my legs.

"Lucy, that was incredible!" I told her, as the realization of what just happened finally began to register in my brain.

"It really was David." she said, then paused for a second before continuing. "So what do you think about maybe coming over again some time? I could share some of my stories with you; maybe give you some ideas that you could try when you get back to school?" she suggested.

I didn't have to think very long before agreeing to that offer, and the two of us sharing stories of our sexual adventures and acting them out became "our thing" for the rest of the summer. I ran out of material a lot faster than she did, but that was just as well because it seemed like Lucy got more turned on, and gave much better details, recounting her sexual past anyway.

Eventually, the summer came to an end and I had to head back to school, which is when Lucy ended things between us reminding me that she was still married and saying that a lot of people would be hurt if we were ever found out. There was always a part of me that expected this and I was actually surprised that she allowed things to keep going for as long as she did, so I didn't take it too hard, but from that point on, I always had an obsession with MILFs.

When I got back to school, I still took full advantage of the readily available college pussy whenever I had the chance, but I also now knew the pleasure that a more experienced woman could give me and was always on the look out for any opportunity that may have presented itself. As luck would have it, I ended up discovering a singles bar in the next town over where there were plenty of mature women who were more than willing to fuck a young college guy to help satisfy my cravings, but those are stories for a different day.