Cocking a Virgin Ch. 02

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Taking her virgin ass.
3.3k words
4.24
58.4k
20

Part 2 of the 3 part series

Updated 10/05/2022
Created 12/10/2012
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After taking her virgin pussy I looked forward to meeting the nubile Neha on Sunday. I now was eager to do her virgin ass. Neha was a small sized girl, who just celebrated her 18th birthday last month. I happened to meet her at lunch with my friend Nisha and things developed so fast that I was in her virgin pussy within a few days.

I knew that her ass would have a difficult time taking in my cock, but I was going to try.......and succeed.

We met at the same place from where I had picked her up the week before. She sat and smiled at me. I patted her cheeks and caressed her thighs. She moaned. "Ready for more adventure, sweetheart?"

She smiled and nodded. I took her hand and placed it on my cock. She squeezed it and started stroking it. I drove on to my farmhouse. As soon as she saw the gate from afar, she ducked and put her head on my lap. She didn't know the ruse I played on her last time. She had her cheek on my aroused cock, and slid her hand inside my shorts and met my bare cock. She gasped, but stroked my cock. I caressed her ass from under the skirt and traced her ass crack. She moaned. I hit the remote on the dash board and the gate slid open, and shut after my car passed through.

I pulled her panty down and caressed her bare ass. She was whimpering. I parked in my garage and pulled her up and kissed her. My hand was on her ass and a finger sliding along her ass crack. She bucked and moaned. I slapped her ass hard and said, "Let's go inside."

Once inside, the little darling was soon naked as I removed her clothes. Her cheeks were flaming and she had a shy smile on her face. I pulled her to me and caressed her back and ass. I put her hands on the belt of my shorts. She understood and soon had my shorts on the floor and a raging cock in her hand. I kicked my shorts away and held her head to my cock. She kissed the tip and licked it. Her tongue circled my bulbous tip and she put the tip in her mouth. As she pushed her head forward to take in the wide tip, her cheeks bulged out. I pushed my cock in and it wouldn't go in much; so tight was her mouth around my cock's girth.

I took out my cock from her mouth and carried her to my bed. We kissed vigorously and she was breathing heavily and moaning with passion. I pinched her nipple and she moaned. I sucked one breast and pinched the other nipple hard. She cried out, "Oh! God. It is paining." I kept the pressure of my fingers on and pulled the other with my mouth till the nipple extended far out and she was sobbing with the pain coursing through her nipples. I kept the pressure on and she sobbed loudly.

This small sexy package was writhing with the torture her nipples were being subjected to. I pushed a finger in her pussy and she bucked her ass up. She was leaking nectar and wriggling her ass with the pleasure my finger was giving her, and she was sobbing with the pain to her nipples. I applied more pressure on her nipple with my finger and she screamed, "No, please. It's painingggg! Please stop......please."

I pulled more with my mouth and she was writing with pain. Tears were flowing down her cheeks and she kept on screaming, "Please.....please...please..." I released both the nipples and she screamed as blood rushed in causing pain. I softly cupped her breasts and kissed this little imp of a girl. Soon she was moaning as I kept pumping my finger in her pussy. I thumbed her clit and she cried out in ecstasy. I kept the pressure on her clit and she was humping her ass in the air. I licked her nipples and she moaned in contentment. I hooked my finger in her pussy to rub her sensitive spot and she hit the roof. She screamed out her pleasure," Oh! My God." I rubbed again as I thumbed her clit hard and fast. She screamed out again and orgasmed. Her ass rose up from the bed and she humped the air.

Spent, her ass hit the bed and she whimpered in happiness. I hugged her and kissed her. I caressed her nipples and she whimpered in pain as they were still sore from my rough handling. I kissed her nipples, and murmured, "My darling baby, soon they will be OK."

She hugged me and said tearfully, "The pain was very high. I felt it would never stop." I caressed her back and kissed her again. She added, "When the pain was intolerable, my pussy was leaking and I became wetter and wetter. I felt as if I was going to orgasm."

I kissed her passionately and she moaned. "My baby, next time I'll make sure you orgasm."

She looked at me fearfully. "You mean, there will be so much pain again?" I nodded and kissed her. She whimpered in fear. I caressed her ass.

I brought her back to wanting by kissing, licking and tugging her breasts and nipples. I licked her pussy and thumbed her clit. She was writhing with ecstasy. I went between her legs and rolled on the protection. I lined my cock with her pussy, and pushed in slightly as she looked on. She whimpered as my bulbous tip entered. I started to pump in and increased the tempo. She was moaning with pleasure and leaking gallons.

I pulled out and she moaned in protest. I turned her over, raised her hips and entered from behind. She moaned as she felt a different sensation. I pumped in hard and fast and she kept on moaning. I caressed her ass and then applied some Vaseline to her rim. She cried out, "What?"

"Easy, my darling, enjoy the massage on your ass rim. The sensations will be different from what you have felt till now."

She moaned as my thumb massaged her rim. The Vaseline was making my thumb slippery. I was pumping in her pussy and thumbing her rim. I applied more Vaseline and pushed my thumb in till her rim spread. She cried out, "No! Please don't."

I caressed her ass and back till she quietened. I pushed in till the first joint. She screamed, "It's paining. Please take it out. Please."

"Hush, baby. Soon you will enjoy this pain."

I twisted my thumb and she sobbed quietly. I pumped in her pussy and in her ass. She continued sobbing. I pulled out my thumb and pushed in my middle finger. She moaned. I pumped my finger and applied Vaseline to my index finger.

"Baby, sweetheart, now take the second finger also."

"Please NO!"

I pushed the index finger inside till the first joint and she screamed, "NO.......Please. It's paining. Pleeaase!"

I caressed her ass and her back lovingly. "It will soon be OK, sweetheart."

She sobbed and I pumped my fingers and my cock. My cock kept her writhing in pleasure and the fingers reminded her of the pain. I caressed her ass and as her moaning reduced, I pumped my fingers and dilated them. The pain shot through her stretched rim and she screamed loudly and sobbed her heart out, "Please stop.....please stop....Oh! My Godddd."

I kept on caressing her ass and back. "Baby, you have to be brave. I know you can take the pain. You nearly orgasmed, didn't you?"

She sobbed and I added, "You have to be ready to take my cock in your ass."

She screamed out, "NO....ooooooo! Please not that. Please, Oh! No! No!" she struggled to dislodge my fingers but I held her by her hips and my knees.

She sobbed, while I kept on caressing her. "Baby, after the pain you will enjoy it in your ass."

She kept on sobbing. I removed my fingers from her ass and my cock from her pussy. I held her to me and soothed her. Slowly her sobbing receded. I kissed her and brought her face to me. I looked into her eyes. "Why are you afraid, sweetheart?"

"You are so big and my ass is very small. Your fingers pained me a lot. Your cock will tear me apart. Please, use my pussy, but not there. Please."

I soothed her and she calmed down. "OK, baby, I won't do your ass unless you want me to." She calmed down and kissed me. "Oh! Thank you."

Soon I was in her pussy and she was meeting my downward thrusts with her push upwards. I pumped hard and fast and we came together. She screamed as she orgasmed. She wept with the release of passion. I held her to me.

It was time for her to leave. She put on her clothes and was ready to leave. "Can I see you again tomorrow? My mother is visiting some relatives and will be away till evening."

I hugged her and kissed her. I caressed her ass and said, "Yes, you can. Only if you let me do your ass."

She froze and a look of fear crossed her face. "No! It will be very painful."

"Yes, baby. It will be painful the first time. It was painful in your pussy the first time, too. After the pain – ecstasy. You have to decide."

We soon left. She was quiet the whole way. I let her think over and decide. When we reached her home, I gave her my number, and said, "Text me if you decide to come."

*******

Early next morning I received a one word text: OK.

I replied: 10:00. Same place.

She was there when I reached the place. She quietly got in. Her eyes were downcast. There was silence throughout the drive. When I turned off the main road on the road to he foothills, and about 2 km before the gate to the gated community, Neha put her head on my lap, on top of my cock. She turned her face down and kissed my cock through my shorts. Then she put her small hand on my thigh and slid it higher till it touched my cock. She held it tight and I moaned. Her small hand felt so nice on my cock.

No words were spoken. She then unzipped my shorts and pulled my cock out. She stroked it lovingly and kissed its tip. She licked and put the tip in her mouth. As my cock was still soft, it entered easily and touched the back of her throat. She sucked it and it slowly responded. She pushed her mouth down and the tip slipped down her throat about half inch. She gulped and her throat squeezed the tip.

My cock started getting hard and the tip blocked her throat. She struggled to breathe and was choking. She shook her head and made guttural sounds. I held her head and pulled hard. Her mouth came off my cock and she was coughing and wheezing.

"What do you think you're doing, Neha?"

She replied after getting her breath back, "I was trying to please you. You wanted to put it in my mouth and it wouldn't go. I thought it would go in when soft. It became hard and choked me."

"You silly girl!" I burst out laughing and she smiled with relief that I wasn't mad. She squeezed my cock and stroked it. She put my cock under her cheek and rested her head on it. I caressed her ass and fingered her crack. She moaned with pleasure. I used the remote and entered the gated community.

We entered the house and Neha went straight to the bedroom. She stood by the bed till I entered. I hugged her to me and squeezed her. I caressed her back and ass and she mewed with pleasure. We both removed our clothes and were soon cuddling on the bed. We kissed hard and our hands were groping each other. Neha was panting and breathing heavily. I went lower and worked over her breasts. I pulled her nipples and she moaned. I tongues and licked them, and tugged them softly. She mewed and was writing on the bed as she became wetter.

I fingered her pussy and she cried out. I pumped her pussy with my finger and thumbed her clit. She screamed, "Oh! God, do it again." I obliged and she raised her ass in the air as uncontrollable sensations ran through her.

I fingered her pussy hard and fast and thumbed her clit hard. She moaned and writhed her ass. My continuous fingering and attention to her nipples with my mouth had her orgasming with a scream.

I was hard and my cock wanted to join the action. I turned her around and raised her ass. I rolled on the protection and entered her pussy from behind. She moaned as I entered her. I started pumping hard. She was moaning as her pleasure increased. I used Vaseline and thumbed her ass rim. She froze and looked back, fear in her eyes. I caressed her ass and her back for a few minutes trying to calm her. She was still tensed. I held her gaze and pushed my thumb in till the first joint. She moaned loudly and looked at me pleadingly.

"I'll be gentle, sweetheart. Get used to my fingers first before the next step, OK?" The fear in her was palpable. I kept on caressing her ass and slowly pushed my thumb in completely. She shut her eyes tight, bit on her lower lip to keep from crying out, and tears dropped down her cheeks.

I pumped in my thumb slowly and twisted it at the same time. The little dear felt the pressure and kept whimpering softly. I kept up pumping her pussy and that kept her wet and contented. I increased the tempo in her ass and she moaned. I withdrew my thumb and she moaned in anticipation of the pain to come. I caressed her ass, applied Vaseline to my middle and index fingers and slowly pushed them in her ass. She sobbed as her rim got stretched. I bent and kissed her back softly and pumped her ass. She moaned and cried out, "Oh! God, Oh! God."

I caressed her ass and slowly dilated my fingers. She cried out as the pain shot through her. I held on to her ass tenderly till she quietened. I pumped my fingers a couple of times more and dilated them again. She cried out. I pumped hard and fast in her pussy and thumbed her clit hard. She was whimpering with passion and she came with a shout. I dilated my fingers and left them separated. It must have pained my little dear. She screamed and I held my fingers open. She became used to the stretch her rim was subjected to. She sobbed and slowly in petered to a whimper as she adjusted to the stretch.

I pumped the fingers and again dilated them and held them open. She moaned and I open the finger more. The pressure was intense and she sobbed, "Please, it is paining. Please stop, please stop." I held on till she again got used to the stretch and started whimpering softly. I pumped slowly and she moaned. I increased the tempo and pumped a few times.

I pulled my cock out of her pussy and my fingers out of her ass. She knew what was coming and moaned, "Please don't, please no!"

I removed the protection from my cock and applied copious quantity of Vaseline to facilitate easy penetration and pumping. Her ass hole was still open, and had not yet returned to its natural position. I applied Vaseline to her rim and she whimpered, "No! no!" I touched her rim with my cock and she gave out a sob. I pushed in and my bulbous tip entered her rim. She cried out as pain coursed through her stretched rim. The dilation had numbed her rim a little and it was some what open. I applied Vaseline to my shaft and pushed in further. She moaned and flexed her rim in reflex action. Her rim tightened on my cock and my cock reacted by expanding. She moaned as it stretched her rim. I caressed her ass knowing it must be paining and that she was bravely trying not to scream.

She slowly became used to the stretch and the pressure on her rim. I pumped in her ass continuously, although not too hard. She became used to the in out motion of my engorged cock. Her small ass and its tight little rim were under tremendous pressure but my dear little imp was trying her best to take all the pain. I moved a finger into her pussy and gave it a workout. She moaned as sensations ran through her pussy. She was leaking juice and my finger moved in and out slickly.

While keeping her happy by pumping her pussy, I increased the tempo in her ass. She was moaning but her pussy was keeping her occupied with different emotions. Soon I was pumping hard and fast in her ass and her moans were less of fear and more of enjoyment. I kept pumping her pussy and flicking her clit. This kept her high and I ploughed her ass with abandon. I was ready to shoot my load and wanted my sweet dear to come at the same time. I thumbed her clit and teased her pussy to distraction. She was moaning and humping her ass and I pumped fast. I came with a shout and soon she orgasmed with a scream of pure gratification. I pumped four or five spurt in her ass and slowly kept on pumping till every drop was squeezed out by her flexing ass.

I grew soft and pulled out. As I pulled out I saw her rim red with friction and stretch. It was pulsating on its own and trying to regain its shape. I caressed both her ass cheeks with tenderness. The poor dear had taken all the punishment I dished out to her small ass. As she lay inert on the bed moaning softly, I kissed her ass cheeks tenderly. I turned her to me and clasped her to my chest and caressed her back and ass. I kissed her on her forehead, her teary cheeks and her lips.

As I held her breasts softly and squeezed tenderly, she mewed with contentment. I kissed her on her lips and pushed my tongue in. I tenderly moved my tongue in her mouth and she moaned with contentment.

"Are you OK, baby?" How's your ass? I know the pain and pressure was much." I kissed her again tenderly. She mewed at the love I was showing.

"I thought I would die. The pain was unbearable but I knew you wanted to do it." Tears flowed down her cheeks. I held her to me and licked the tears from her cheeks. The little dear was just 18 and very small. Small body, small breasts, small ass and a very tight ass rim, but a big heart. I'd subjected her to great pain.

Then she said, "In the end all I felt were the unbelievable emotions and passions running through me. The pain seemed nothing compared to the feelings that I experienced when I orgasmed so many times."

I hugged her and caressed her all over. She mewed with fulfilment.

Then she said, still very shy, "I'm very sore. But next week I want you to do my ass again."

Oh! My baby," I clasped her to me and hugged her tenderly.

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AnonymousAnonymousalmost 8 years ago
Seriously GOOD!

Dear GOSH is this good!! (And I know good- been reading Literotica stories since I was seventeen... ) Between the dialogue, the wording used, the storyline, and the characters, ... ohmygosh I have no idea who you are but THANK YOU!!! (:

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