Aunt Sandi Ch. 14

I laughed and said, "Aw man. I was hoping to have a four-way with all of you. Jill could make some kind of dessert and I could eat it off your bodies."

Amy giggled and said loudly, "Ha! You wish!"

She thought about it a moment and then admitted, "Hmm, that does sound like fun. Maybe I should ask them if they're up for that sometime."

I shouted, "Yes! Now you're talking!" and pumped my fists in the air.

Amy said in an erotic, low tone, "I have seen them naked. They both have nice bodies. I bet you'd just love to shove your hard cock into their wet pussies as you lick whipped cream off their tits." Amy's expression was dead serious.

I looked at her and said seriously, "I was only messing around. I didn't mean that."

She giggled and said, "I know, silly. I was just fucking with you." She laughed very hard and pointed at me and said, "You should see your face right now! Priceless!"

I groaned and said, "You're so mean!"

Amy asked, "So, how much longer do we have? Can you go again?" She raised herself up and pulled off her robe and threw it on the floor.

"I think I can, I think I can."

Amy giggled. "Let me see if I can get your little engine going again."

She crouched beside me, taking my cock into her mouth. As it started to grow, I scooted my way over and pulled on the side of her leg to get her to let me crawl under her into a 69 position.

She figured out what I was doing and quickly shifted on top of me. She scooted back and her pussy came down onto my face. A good amount of semen was leaking from her vagina, and as I had become used to doing, I simply licked her clean without even thinking about it.

As I did this, Amy stopped and looked back at me and asked, "I have to know. Did you just do what I think you did?"

I said, "I, uh... I guess I did. It's something Sandi likes me to do. Does it gross you out?"

"Are you kidding? It's hot! I noticed you doing that yesterday too but I was too scared to say anything. There's more where that came from. Watch..." She clenched her vaginal muscles tightly and pushed out all the rest. Her muscle control and conditioning was nothing short of amazing.

She resumed sucking on my cock, which was now completely hard again.

I stretched up a bit so I could lick her asshole, causing her to reposition herself slightly so I could more easily get to it. Soon, I was sticking my tongue inside her ass as far as it would go. She pushed back against me and moaned each time it went in, and before long had a small orgasm. Her anus squeezed my tongue over and over as she came. I switched to sucking on her clit and she came again, really powerfully. This was so arousing to me that I came as well. I was really starting to love the ease in which Amy was able to climax.

Panting, Amy collapsed on top of me. After a minute or so, she climbed off and lay beside me. She whispered, "That was intense. I love it when you lick me back there. It feels a lot different than my clit, but still amazing."

"Maybe next time you'd like something bigger in there then," I said and winked.

Sheepishly, she said, "That's something I've never done before. Well, other than with a finger when I do it myself. The boyfriends I've had must have thought that liking anything to do with an asshole must mean they're gay or something, so it's just never happened."

"I'd be happy to do it with you if you'd like to try."

"I would. If it's better than the way your tongue feels, I'm on board."

"Cool. Maybe we can do that tomorrow. Just prepare at least an hour before."

"Prepare how, exactly?" she asked.

I was a little embarrassed, but I managed to say, "You know, be sure to poop and wash well with soap and water."

She smiled and said, "Oh, OK. I thought you were going to tell me I had to do an enema or something, which didn't sound like much fun. I can totally handle pooping and a shower." She giggled.

I laughed and said, "Great." I looked over at Amy's clock and said, "It looks like I need to get going. I'm just going to jump in the shower for a minute."

"Are you going to have any lunch at all? I wouldn't feel good if you're going hungry all day just to be here with me."

"I didn't really think that far ahead. The only thing on my mind was you. But, I do feel a little hungry. I'll just grab some drive-thru on the way back."

"That may be OK for one day, but tomorrow I'll get Jill to make up something for you."

"Wow, thank you, and thank Jill for me." I kissed her gently and went into the bathroom to take a quick shower. Amy thoughtfully had a towel ready for me to use sitting on the bathroom's countertop.

Amy followed right behind me and sat down to pee just as I started to pull the shower curtain closed. She said sheepishly, "I hope you don't mind. I really need to go. Before you got here, I was, um, getting myself ready for you and I forgot all about peeing."

I smiled and said, "Go right ahead. It makes me happy that you're comfortable enough to do that in front of me." She smiled.

I quickly finished the shower and got dressed. Amy put her panties and robe back on and walked to the door with me. She said, "So, tomorrow?"

"You bet. I wish I didn't have to go. One hour isn't enough. I could definitely go again." I smiled.

"I know. But, I had a wonderful time. I'll be thinking of you."

We shared one final kiss before I left to head back to work.

* * *That afternoon, Amy and I did our best to talk as we usually did. We somehow managed to keep our hands off of each other for the most part and didn't mention anything related to our new relationship.

When it was time to leave, Amy was saying goodbye, but she scooted up next to me and grabbed a pen and wrote, "Wait in stairwell" on a piece of scrap paper. Once she made sure I read it, she crumpled the paper up, threw it in the trash and walked away.

I headed to the stairs and waited. Amy came in a minute later and sighed and said, "I just wanted a proper goodbye kiss."

Amy's "proper goodbye kiss" went on for five minutes straight. We finally broke apart when we heard a door a few floors above us loudly open and someone coming down quickly.

Amy sighed loudly and softly said, "Damn." She quickly kissed me one last time and whispered, "See you tomorrow."

I touched her cheek and smiled into her eyes for one last second and quickly headed home.

* * *On Thursday morning, Sandi shook me awake and whispered in my ear, "Honey, do you think you could do me real quick? I can't get the idea of playing with you and Amy together out of my mind, especially now that we know she's up for that."

Without words, I moved beneath the covers and found that Sandi's pussy was already wet. When I touched my tongue to her clit, it was already standing up at attention, and it only took about a minute before she tensed up and came.

She said breathlessly, "That was just what I needed." I laughed and popped out from under the covers and said, "My turn."

I pushed my penis all the way inside her and was about to start thrusting when Sandi stopped me and said, "Shouldn't you save yourself for taking Amy's anal virginity?" She grinned.

I wasn't so sure I wanted to stop, and it occurred to me that this might be one of her tests to see how my dominance training was going. I took a chance and said confidently, "Let me worry about that. Right now, I'm going to fuck you hard."

She didn't respond with words, but her face formed an expression of shock and surprise. The faintest hint of a smile hiding in her eyes told me that this definitely was a test.

That hint of a smile irked me a bit, so I grabbed her wrists and pinned her arms above her head.

I got down to fucking her, steadily increasing my rhythm. She closed her eyes and her expression morphed into one of complete pleasure. She moaned and arched her back and let herself go.

I said, "You love my cock in your pussy, don't you?" She nodded furiously.

When I started to feel myself getting close, I decided to take it a step further and directed, "Sit up and take my cum all over your face." I let her wrists go and got into position.

Instantly, she partially sat up, closed her eyes tightly, opened her mouth and got ready. I positioned myself a few inches from her face and unleased. The jets of cum sprayed her cheeks, into her mouth, on her chin and dripped down to her tits and stomach.

I grunted, "Suck the rest out. You love my cum, don't you?" She opened her eyes, and while moaning loudly, she took my cock into her mouth as far as she could take it and sucked it for another minute until nothing was left.

I looked down at her and said, "Now clean yourself." She smiled and dutifully scooped all of the little pools of cum from herself and swallowed them all down.

When she was done, she sighed deeply and collapsed down on the bed with a thud and smiled the happiest smile possible. She simply said, "A fucking plus!"

For a while now, she had been giving me grades on how well she thought I did during her tests, and lately I had been getting better grades and less and less constructive criticism.

I laughed and asked, "What do I get if I get all A's on my report card, teacher?"

She sighed and said tenderly, "You get... fuck, I don't know. I'll give you anything you want." She looked right into my eyes and with tears welling in her eyes said, "Daniel... I love you more than life itself."

I was taken completely off-guard. Before this very moment, Sandi had only said that to Mom, and maybe to Uncle Kurt when he was alive, I didn't know and would never ask. It came from a place of utter and complete devotion, and I honestly never thought she would say it to me.

I got over the initial shock and said back, "I love you more than life itself." I bent down and kissed her tears away, and we held each other there in the stillness until we were both almost late for work.

As we were rushing to leave, Sandi asked, "Do you know if she has lube? Maybe you should bring some of ours just in case. And if she's anything like me, she won't like what happens later if you cum inside her."

"Not sure but I'll bring it just in case." I ran back to the bedroom and grabbed a small bottle out of Sandi's nightstand.

"I just remember back to my first time. It did not go well at all and it hurt for days. But I know I've taught you how to be gentle, so she's in excellent hands."

* * *When I got to Amy's apartment, she opened the door and had a very concerned look on her face.

I became concerned immediately and asked, "What's wrong? Did something happen?"

"I'm... I'm worried. I don't know if I can go through with it. I've never had anything close to that big in there. I read a lot of things online where women got tears and anal fissures and bleeding when they tried it. What if that happens to me? I'm so scared! Can we maybe just not have sex today? I'm really not in the mood. I'm so sorry." She seemed to be on the verge of sobbing.

"Oh my... Of course we don't have to. I would never make you do something you're not totally comfortable with. Let's just talk about it." I held her until she calmed down.

Amy's expression visibly softened. She said, "Oh, thank God. Thank you for understanding. I do have lunch for you. At least let me feed you some of Jill's home cooking."

"Oh, cool." We sat down at the kitchen table and ate lunch, which consisted of very flavorful pork tenderloin and some of the best homemade mashed potatoes I'd ever had.

"Jesus, what does she put in these potatoes?"

Amy giggled and said, "She uses full-fat heavy cream, Kerrygold Blarney Castle cheese, Kerrygold butter, and some secret spice blend that she grinds herself in them. They're awesome, huh? And the barbecue sauce on the meat is her own recipe." I didn't open my mouth long enough to respond and just kept scarfing down the delicious food. I thought to myself that whoever ended up marrying Jill was going to die a very fat, very happy man.

Finally, I said, "Please give my compliments to the chef. Tell her if she ever opens her own restaurant, I want an invite. And once I get in, I may never leave."

Amy smiled and said, "I'll be sure to let her know that. I told her how much you liked her bacon and she got the cutest little smile on her face."

Once we got done, I insisted on helping to wash the dishes again, and while we stood at the sink we talked about anal sex.

I told her, "I can't see how you'd ever have any damage as long as we prepare properly. The main things are to have patience and use a lot of lube, and I brought some good stuff with me. You need to work up to being able to take a penis inside you. The easiest way is to start off slowly with just one finger and then put more in as your muscles relax. I have a feeling that the women that were hurt had guys that jammed themselves in dry or something stupid like that."

Amy sighed and said, "I should have known that you would know the best way to do it. Sometimes I go a little crazy with reading all the terrible things that can happen online. Have a persistent cough? Oh, you must have stage 12 brain cancer."

"Right. WebMD and the like used the wrong way can be really scary." I laughed.

As we finished with the last of the dishes, she asked, "Well, do you think we could at least try the finger part today? We don't have time to do much else."

"Are you sure? You're not upset anymore?"

"I'm sure. Actually, when you described the process, it made me all tingly." She giggled.

"I don't know... If we get started, it's going to be really hard to stop," I said worriedly.

"Please?" she begged with a face that would give Puss in Boots a run for his money.

"Did you get clean for me?". She smiled and nodded.

We moved to her bed and got naked. I said, "The main thing to remember is to relax, relax, relax. OK, lay on your back for me. It goes a lot easier if you're fully aroused."

Amy got into position and I moved down and began licking her clit and pussy. In a few minutes, she was moaning and arching her back.

I popped open the lube and said, "OK, this is going to feel wet and cold in 3, 2, 1..."

I pressed my lubed fingertip against her anus and very gently inserted it.

She giggled and said, "What is this, Anal Mythbusters?" I laughed too, not realizing that it sounded like that. She immediately added in her best TV announcer voice, "Coming up next on an all new ButtBusters..."

As her giggles subsided, I said, "Clever girl," and licked her clit directly a couple times, causing her to miss my Jurassic Park movie reference. She gasped and immediately became quiet and said softly, "It feels good so far."

I pushed my finger in until it was completely inside. Amy said, "It feels... strange. Not bad. Like I need to poop." I flicked my tongue across her clit and she grunted and squeezed her muscles tight and moaned "Ohhh!"

"What about those feelings together?" I asked.

"Really good!"

"Here comes the second finger. Ready?" I looked up and saw that she was nodding.

I pulled out the first finger most of the way and got a second one covered in lube and slowly pushed it in. I very lightly licked near her clit to provide as minimal stimulation as I could. I didn't want her to cum yet.

"You're doing fantastic. Ready for more?"

She groaned, "Yes..."

I lubed and began inserting the third finger and was met with a lot of resistance. "Ouch, it's hurting! Stop!"

I pulled back the third finger and left the other two in just barely to give her time to recover and said, "Sorry, I went a little too fast there. Just give it a minute and try as best as you can to relax. It's going to be alright. Nothing is damaged."

"OK," she said uncertainly.

"Breathe for me. Breathe in the deepest possible breath you can, hold it for a couple seconds and let it out slowly. Do that for me three times."

She followed my instructions to the letter and I increased the pressure my tongue was making around her clit until she started to moan again. Finally, I could feel her sphincter relax, so I put the third finger back in and very slowly pushed it in.

It took some time, but now all three fingers were fully inside her. I said, "Amy, my dear sweet Amy, you did it. I have three fingers all the way in."

She gasped, "Oh God! I can't believe it! It feels incredible." She looked down at me and, with an expression filled with desire said, "Fuck my ass! I want it so bad!"

"But you said..."

"I know! But we're so close. Please don't leave me on the brink..."

I knew instantly that if I left, it would fill both of us with a huge amount of regret. I slowly pulled my fingers out and said, "I won't leave you."

Amy sighed and whispered, "Thank you."

I moved into position between Amy's widely spread legs and said, "Pull your legs up to your chest and hold them there."

She did and I placed the tip of my cock at her opening and applied a lot of lube. I said, "OK... Remember, relax."

I pushed and the tip quickly disappeared inside. Amy moaned and asked, "Is that it? That was easy."

I smiled and said, "Not quite there yet; that was just the tip. Here comes more. Keep breathing."

I very slowly pushed more inside her. I could feel Amy squeezing her muscles rhythmically, so to intensify her pleasure further, I inserted two clean fingers into her vagina and massaged her G-spot in time with her squeezes, causing her to moan loudly. I continued pushing in until I was all the way inside.

I gasped, "It's... in..." I pulled nearly all the way out and started slowly thrusting until I felt she was ready, then began moving faster. Amy was just gasping in air and groaning loudly as she exhaled. Her muscles clenched and unclenched around me incredibly powerfully and created sensations I had never felt before.

It was too much for me. Before I could gather my thoughts enough to pull out, cum started squirting from my cock like a fire hose. I partially lost my balance and crashed down onto Amy's upheld legs, pressing them hard down against her tits, all the while still squirting my load deep inside her.

Amy's eyes flew open wide and she screamed loudly and came. She yelled, "No!" All of a sudden, I felt a stream of hot liquid spray my stomach and groin area. Given my experiences with Sandi, this exact feeling wasn't unfamiliar so I remained calm. I pushed myself back up and started to slowly withdraw myself.

I looked down and I was wet on my stomach, groin, and thighs, and there was a small dark wet spot on the bed as well.

Amy was gasping for air. She brought her hands up and covered her face. She finally said, "Oh God, I peed! I'm so sorry!" She began sobbing.

I didn't really smell anything, so I said, "It doesn't smell like pee." I leaned down and sniffed the bed and her pussy and said, "It's not pee." I licked some of the fluid from her pussy and said, "Amy, you squirted. Has that ever happened before?"

Amy shook her head vigorously "no" and still had her face covered. She finally stopped sobbing and I asked, "Are you OK?"

Again, she shook "no". I leaned forward and grabbed her wrists and pulled her hands away. I softly said, "I need you to open your eyes for me. Try to breathe and calm down."

She forced her eyes open and I said, "You didn't pee. And even if you had, it's completely fine. Here, taste it and you'll see."

I slid my finger through the pool of wetness between her legs and brought it to her lips. She tentatively sniffed it and then opened her mouth. She tasted the juice and immediately sighed and visibly relaxed, and that made me relax as well.

I asked, "Did it all feel as wonderful as it sounded?"

Amy breathed in deeply and said, "Wonderful doesn't even begin to describe what it felt like. We have to do it again, and soon."