My Daughter's Best Friend Ch. 03

This is the third chapter in the ‘Cindy’ series. If you need the backstory on our two love- birds please read the firs two chapters. Please feel free to write me with your comments. That’s the fun part of writing these stories.

Cindy and I were just lazing in bed one evening. We had just made love and we were enjoying our post coital ‘glow’. With Cindy’s schedule moments like this were rare and meant to be savored. She was dozing and I was playing with her behind while I watched TV. Nothing particularly sexual, just enjoying the feel of her tight, young cheeks, occasionally tracing a finger along her butt-crack.

“You really like my butt, don’t you?” Cindy asked sleepily.

“It’s a cute little butt, alright.” I said, giving her ass a gentle squeeze. “Am I bothering you?”

“No. But every time we have sex you do something back there. Sometimes you kiss it or lick it. Sometimes you put your finger in it.”

“Here. You mean?” I said as I massaged her butthole with the pad of my middle finger. Cindy cooed and wiggled her butt a little.

“Yeah, there.” She giggled. “Know what I think? I think you’re a dirty old man and you wanna put your big old dick in my ass. Look! You’re getting hard just thinking about it!”

It was true. Despite having just made love to her, the thought of easing my 45 year old cock up her tight 18 year old ass was making me horny again. “See, you are just an old pervert.” she said as she rolled over and took my cock in her mouth. Cindy spent several minutes just savoring my penis, sucking the head, licking the shaft and fondling my balls before she got up and straddled my hips.

Years ago my late wife had a very difficult time in childbirth with my daughter. Her doctor recommended that she not have any more children. Rather than have my wife endure the invasive hysterectomy procedure I opted to get a vasectomy. While I knew there was a good reason for it I still harbored some resentment against my wife because of it. But tonight, as my cock slid into the tight, wet confines of Cindy’s teenaged cunt, I think it was the best thing I’ve ever done. With know fears of pregnancy, Cindy and I could enjoy each other without a condom coming between us.

Cindy impaled herself fully on my cock and lay down on top of me. Instead of humping against me she stayed still, squeezing me with her pussy muscles and occasionally moving her hips, just enjoying the feeling of me inside her. She began kissing my face, softly, gently. She nibbled my earlobe and ran the point of her tongue around the shell of my ear. She was driving me crazy.

“Touch me there.” she whispered in my ear. My hands traveled down her body, from her shoulders to her back, to the swell of her hips, to the firm, round cheeks of her ass. Cindy held me tight when I spread her ass and let a finger caress her back hole. Her body went tense when I pressed against her sphincter, slippery with her pussy juice and and slid in up to the first knuckle. She rocked against me while I slowly fingered her ass.

Cindy sat up and wiggled her hips, taking my finger deeper in her virgin ass. She looked deep in my eyes, her face a mask of lust. “I knew you were a dirty old man.” She leaned down and kissed me hard. Our tongues danced and I fingered her faster. Cindy began to tremble, a sure sign that she was about to come.

Cindy surprised me when she pulled away before she orgasmed. She slid off my cock and away from my invading finger. Taking my face gently in her hands she said “Take my ass. I want you to fuck my asshole.” With that she got on all fours and presented her perfect backside to me.

I didn’t need an engraved invitation. I buried my face between those glorious cheeks and kissed her asshole. While I rimmed her I massaged her clit. Cindy gasped and bucked against me and came. Hard. It took her a few minutes to regain her composure after such a hard orgasm, but her lust was undimmed. Assuming the doggie position again she said “Please! I want to feel you in my ass!”

“And so you shall.” I replied. “But you’re not ready for that, yet.” Giving her a playful swat on the behind I turned her on her back. “Relax, I’ll be right back.” I went to the bathroom, my hard-on pointing the way, and got a tube of Vaseline out of the medicine chest and returned to my room. I made one short stop at my dresser to get one more important implement of pleasure and the turned to my horny teen lover.

I pulled Cindy so that her butt was just at the edge of the bed and knelt between her legs. Once again I began licking her pussy. She purred as I gently sucked her clit between my lips. While her attention was on the tongue lashing I was giving her I squirted a generous dollop of Vaseline into my hand. While Cindy ground her pussy into my face I started smearing the slippery goo on her tender asshole. She tensed up at my touch.

“No, baby.” I said. “Your little butthole wants to tighten up but you can’t let it. You have to welcome me in, or else it will hurt.” I continued speaking softly to her, relaxing her, until my finger slid easily up her poop chute. I resumed eating her pussy while I fingered her ass and soon she was as relaxed as she was going to get.

“Are you ready?” Cindy licked her lips and nodded. I leaned over and kissed her, then placed her legs over my shoulders. “This way I won’t go in too deep at first and if it hurts you can push me away. I explained. “Just try not to shoot me across the room!” I added with a laugh.

I slathered more Vaseline on my penis and lined it up with her anus. “Remember what I said, baby. Don’t fight me let me in.” I pressed forward and I could feel resistance. Cindy was trying to relax her self and the head of my cock slid into her. I asked her if she was okay and she smiled bravely for me. I remained still and stroked her stomach and legs reassuringly. I maintained eye contact as I slowly worked my hard dick deeper into her. Her eyes went wide when the last of me slid into her distended ass and she felt my balls press against her cheeks.

“Oh, my god.” she squeaked. “You’re all the way in my ass.”

I let her relax a moment, not fucking her but gently stirring my shaft in her butt, getting her used to the penetration. When I could see she was relaxing I pulled out my other surprise. Cindy had closed her eyes to savor the new sensations she was experiencing and then I switched on the vibrator I had brought along, gently running it along her pussy slit. Cindy gasped and arched her back when I buzzed her sensitive clit, burying my cock deeper in her backside. Slowly I began pumping her butt while buzzing her sopping wet pussy. She began twisting her own nipples as the intense pleasure began to overwhelm her. I increased my pace, both with the dildo and my dick and Cindy began to come.

“Oh, shit! Oh, god!” she yelled. Then her mouth and eyes both snapped wide open as a powerful orgasm shook her body. Her body shook and her asshole clamped down on me hard, almost sucking the come right out of me. Then with one powerful thrust of her legs she pushed me away from her.

“Oh, Jesus. If I come that hard again I think I’m gonna die!” she exclaimed. Her hair was drenched with sweat, her nipples were standing out like marbles and her inner thighs were slick with her own pussy juice. “I’m as ready for this as I’m ever gonna get.” She declared and assumed the doggie position again. This time I wasted no time getting behind her and sliding my manhood deep into the welcoming recesses of her ass.

Cindy pushed back against my thrusting tool, taking as much cock as she could get. I grabbed her hips and started fuck that pretty, teen ass for all I was worth. Cindy lowered her and reached between her legs to frig her clit while I sodomized her. Cindy was moaning and crying out with passion. I fucked her as hard as I dared to and she shouted out her encouragement.

“Oh! You dirty old man! I used to play with your daughter and now you’re fucking my asshole!” she moaned.

“Fuck me! Fuck my ass! You old pervert! You used to buy Girl Scout cookies from me and now you’re buttfucking me!”

The sight of my cock pistoning in and out between those beautiful buns, her little girl voice talking dirty to me and the feel of her tight, no-longer-virgin asshole gripping became too much for me. With a roar I rammed my cock as deep into her ass as I could and unloaded a hot load of come.

“Yes,baby! Come in my ass! Let me have your hot sperm!” she screamed. I have no doubt that the neighbors could hear everything. Not that I care.

Finally I pulled out of her behind. Cindy and I faced each other and I kissed her. My sperm was leaking from her behind. We were both covered in sweat and breathing hard. The bed was a disaster area.

“So, how did you like it?” I asked.

“Oh, my god. That was way more intense than what I expected.” she said. “I didn’t expect to come from a dick in my ass.”

“Well, I guess I do have some talent.” I said assuming false bravado. “So, do you think you’ll want to try it again?”

“Definitely,” she said with a grin. “But not for a few days. I think I might be a little sore tomorrow.