First Anal Sex: My Experience. Share Yours.

[monger_ind]

I cant stop myself from cumming before I complete reading your post.

[Mark_2000]

Originally Posted by monger_ind

I cant stop myself from cumming before I complete reading your post.

I had the same problem with her. I was forever having to change positions to stop myself from cumming.

I found I always lasted longer in her pussy.

As the relationship developed, she wanted to involve more of her fantasies around the ass sex. It greatly increased the sexual tension and excitement, which made the sex so much better than just ordinary fucking.

We never did any fantasies with the pussy fucking. I suppose the taboo involved with anal let her get in touch with her wild side.

Don’t be afraid to click thanks if you liked it.

.

[daskers]

Friends sister that I dated years ago. We was going at it real good one night and she told me stick it in her ass. That was my first experience with it.

[Mark_2000]

Originally Posted by daskers

Friends sister that I dated years ago. We was going at it real good one night and she told me stick it in her ass. That was my first experience with it.

Can you elaborate on the experience.

More details.

How was it?

Did she like it?

Did you do it again?

[Mark_2000]

Talking one night after sex. She spoke about how much she enjoyed being. dominated while dressed as the French maid. She also added that being restrained had further aroused her. She expressed her desire try that again and to take that to another level.

“What did you have in mind?” I asked.

“Nothing, I want you to be totally in charge of this one.” She replied.

She further added. “Surprise me. Be as rough as you like.”

I thought about it and decided on a simple plan, light on fantasy and heavy on the torture element.

I never discussed it further with her and I think she forgot about it. I waited until the next time we would be alone in the apartment. I arrived there before her and waited. By the time she eventually arrived home after lectures, it was dark. She unlocked the door and reached for the light switch. I grabbed for her arm and and twisted it behind her back. I clamped my other hand over her mouth and with the weight of my body, forced her up against the wall. I leaned in close to her ear and said.

“Keep quiet, Do as your told and you might get out of this alive.”

She nodded in response, her eyes wide with fear. As I turned her around, one hand got free and she went to slap me. Having anticipated her move I blocked her and quickly man handled her to the floor.

“Right b*tch, you’re going to really get it now.” I shouted.

I grabbed for one of the stockings I had in my pocket. I quickly tied it over her mouth , gagging her. I reached for the other stocking and quickly tied her wrists behind her back. I grabbed her restrained arms and dragged her to the couch and threw her down. I undid her jeans and went to pull them down, she kicked her legs in defiance and I slapped her again. As I got her jeans free from her kicking legs I proceeded to use the jeans legs to tie her ankles together. Suitably restrained I stood up and admired my work. I next forcibly ripped her blouse off, buttons flying as they separated. I pulled her top down until it was stopped at her restrained wrists.

I pushed her onto her back and straddled her. I slapped her breasts for good measure. I reached down and grabbed both nipples and firmly pinched them. I kept increasing the pressure until they glowed bright red. All the while she strained against her gag. I released my grip, lent down and bit into her left nipple. By this time she was writhing in ecstasy.

I clamped my teeth and increased my pressure on the nipple. I kept still and let her movements increase the pain.

I hopped off her and flipped her onto her stomach. I ran my hand down her back, across her buttocks and down her thighs. When I could see she had relaxed, I slapped her buttocks a few times and then massaged them. I then spread her ass cheeks and roughly inserted two fingers and finger fucked her. Once she was good and loose, I lent down and spat in her asshole, then forced my fingers back into her. I finger fucked her for few minutes. Knowing I had to continue with my plan I withdrew my fingers.

Grabbing her by her hair, I pulled her up from the lounge and dragged her over to a dining room chair. I needed more restraints, I left her and went to the bedroom and collected, a scarf and a pair knee high socks. I returned and unrestrained her. With her now facing the chair back, I quickly tied her wrists and ankles to the chair.

I grabbed the piece of cane I had brought with me and started to whip her ass. After a dozen whips I stopped. Her buttocks were now covered in fine red welts. I now went around to her face, untied the gag and forced my cock into her mouth. I let her suck at first then I grabbed her behind her head and forced my cock down her throat until she gagged. I then proceeded to fuck her throat, pulling on her head to meet each thrust. After a couple of minutes I’m well and truly covered in drool.

Pulling her ass right to the edge of the chair. I knelt behind her and entered her ass. As I thrusted into her I reached around and rubbed her clit. I then inserted two fingers into her pussy and finger fucked her. I continued to fuck her with increasing speed and force.

Needing to continue the torture, I withdrew and untied her. By this time all the fight had gone out of her. I carried her into the bedroom and threw her onto the bed. I quickly restrained her wrists above her head and retied her ankles.

I got her vibrator from the drawer, turned it on and started to slowly work my way down her body. I stopped at her nipples and gently teased them with the vibrations. After a couple of minutes I continued down her abdomen to her thighs and worked my way back up. I now held the vibrator to her clit. I allowed the vibrator do all the work. As she started to lift her hips and her moans increased I pulled the vibrator away, to deny her an orgasm. I then started to vibe her clitoris again. Once her orgasm was close I withdrew the vibrator. She pitifully begged.

“Please let me cum.”

“You can only cum when I say you can.” I admonished her.

Having finished the clit torture I lifted her onto her knees. I went around behind her and slapped her ass another couple of times. I climbed up onto the bed and squatted above her and slid my cock in her ass. I fucked her hard for a couple of minutes. Occasionally I gave her ass a good hard slap. Once again I pulled out of her. Turned her onto her back and inserted 2 fingers into her pussy and roughly finger fucked her. Once close to orgasm again I stopped. She kept thrusting her hips up into my hand. Not wanting her to cum I withdrew my hand.

I untied her wrists and ankles. I grabbed her by the hair and pulled her into the bathroom. I turned on the shower and quickly stripped. We both hopped into the shower. I got the shower head and brought it down on its attached hose and placed in front of her clit. Within a few minutes of this water torture. She demanded.

“I need to cum.”

I relented and told her. “ You may now cum.”

Within a minute she screamed her way through her first orgasm for the evening.

We returned to the bedroom. I restrained her arms above her head. I got her large butt plug and pushed with increasing pressure until her ass relented and it slipped in. I next got her dildo and slipped it in her pussy. I reached for her vibrator and turned it on. I now held the vibrator to her clit as I started to fuck her with the dildo. With her ass, pussy and clit being stimulated simultaneously, she soon came. I kept going and after her third orgasm. She pleaded with me.

“Please, I can’t cum anymore.”

I asked her if she wanted to continue. She nodded. We went out to the lounge room. I put Black Sabbath Paranoid album on, it soon blasted out the speakers. As she lay on the floor, I held up her dildo and ordered her to fuck herself with it. Taking it by two hands she thrusted it in and out of her pussy. I moved in and lifted her legs until her feet were dra*ped over my shoulders. All the while she continued to fuck herself. I now entered her ass once more and soon matched the pace of the dildo thrusts. Holding her thighs I pulled her into me to meet each thrust.

“Please rub my clitoris.” She begged.

I reached down with one hand and rubber her pussy. Seeing she was close to her orgasm. I said.

“You can cum now.”

She came with a scream. When it was over she pulled the dildo from her pussy and tossed it aside. I now picked up the pace and thrust harder into her. She begged.

“Please cum in my ass.”

Just as the song Ironman came to its frenetic ending I came in her. Exhausted I collapsed down on top of her. As I caught my breath I asked.

“I hope I wasn’t to rough on you?”

“You know me, I’m pretty tough.” She replied.

I asked what was her favourite part of the evening. She told me her biggest turn on was not knowing what would come next.

“That and the ass fucking of course.” She added.

She thanked me with a kiss. I kissed her back.

[Mark_2000]

This happened one night after a few drinks. We were engaged in our usual ass play. I was eating her pussy and fingering her ass.

I started to massage the flesh between her pussy and ass. She obviously found this very pleasurable as she started to moan louder. She then placed her hands behind her knees and raised her legs to her chest. I pulled back and was admiring the sight of her asshole. She then started to relax and contract her muscles causing her asshole to open and close. In effect she was winking at me with her brown eye.

I lent back down to eat her pussy. I massaged her perineum with increasing pressure. She again moaned louder. I then lowered my tongue to the area and started to lick with more pressure. My tongue strokes got longer I was now licking the outer part of her asshole.

I now lowered my mouth to her asshole. I started to gently blow breaths of alternating warm and cool air over it. Her asshole twitched in response.

Not knowing how she would react I started to lick the flesh around her asshole. The smell of her ass was an incredible turn on. Encouraged by her moans I licked in an ever decreasing circle and was soon massaging her asshole with my tongue. She seemed to like it, I licked with increasing pressure with the flat of my tongue. Her ass had no real taste just mainly lube and a slightly bitter taste. She was always very clean. I was starting to enjoy the experience, being urged on by her response. Now with the point of my tongue I licked the inner ring of her asshole and applied increasing pressure with my tongue. Suddenly her asshole relaxed and my tongue penetrated her. She immediately responded and pushed her hips up. My tongue was forced deeper into her ass.

I now started to twirl the tip of my tongue into her ass. By now she was moaning loudly. I constantly changed the width of my tongue while I licked, it helped to stop the tongue cramping. I alternated between circular licks to just random shapes. She never knew what to expect, which heightened her arousal.

I now reached up and gently massaged her clit with my thumb, causing her to respond by thrusting her butt back into my face. I built up the pressure and speed with my thumb and quickened the pace of my tongue. In no time she orgasmed and her opening nipped at my tongue.

I know flipped her onto stomach, spread her ass cheeks and delighted in the sight of her puckered asshole as I stroked myself. Once hard I lent in and with increasing pressure my cock entered her asshole. She raised her hips to deepen the penetration. I now sped up my thrusts, she responded by pushing up to meet each thrust. I noticed how sexy her back was, being a swimmer, she had quite developed musculature.

I lowered my head and licked up her spine. I now lay my weight on her and stopped thrusting. She responded by by swiveling her hips around my cock and added to the pleasure by contracting and relaxing her ass. I closed my eyes and enjoyed the feeling. At her insistence I started to thrust back into her ass. Going as deep as I could with each penetration. As I bottomed out on each thrust she would exhale a loud gasp.

Wanting to extend the pleasure I pulled out of her, I kissed up her spine and back down again stopping at her asshole. I again proceeded to lick and insert my tongue. She was soon pushing her ass back against me forcing my tongue deeper into her now open asshole. I swirled my tongue around reaching in as deep as I could. She responded and started to rub her clit.

With my tongue tiring I withdrew it. I rolled her onto her back and gently started to to lick up her tummy and gently massaged her pussy. Arriving at her breasts, I gently took her nipple into my mouth and sucked. I continued to tease her nipple with my twirling tongue. I reached up and massaged her other breast. After a few minutes I changed nipples and continued with my mouth. I raised my head and now kissed her gently on her lips, she responded and kissed me passionately. She obviously had no problem with where my tongue had been a few minutes before.

I raised her hips and placed a cushion under her ass. I was on my knees and entered her ass. I raised her legs up against me and built up pace. As always she started to rub her clit again. She started to talk dirty, knowing that always turned me on. In no time she started to moan and as our pace built this transitioned in to screams. My balls tightened and I came just after she did.

That was our first experience at rimming, something we decided that we both really enjoyed. It was just another item we added to our increasing repertoire of sexual acts.

I did not always rim her as part of our foreplay. Sometimes she preferred the deeper stimulation of an ass fingering.

But when she was feeling in a submissive mood, a good ass licking really got her going. I always delighted in hearing her say.

“Please lick my ass, baby.”

It was something I happily did, she however never reciprocated and I never asked.

It had to inevitably happen. One night she was sucking my cock and cradling my balls with her hand. With her other hand she started to massage the flesh between my scrotum and ass. It felt pretty good, encouraged by my moans she massaged in a circular manner with increasing pressure. I decided to go with it and relaxed. She massaged in larger circles and soon her finger connected with my asshole. I must have gasped, she allowed my cock to slip from her mouth and said.

“Relax, you’ll enjoy it.”

I had always been curious as to how it would feel and relaxed. Her fingers now massaged the flesh around my asshole. She massaged in an ever decreasing circle and was now directly massaging my asshole. I felt the increasing pressure and I breathed deep, as I exhaled her finger entered me. It felt uncomfortable at first and I concentrated on my breathing and tried to relax. She removed her finger and coated it with lube, looked at me for acknowledgment and reinserted her finger. After awhile the discomfort disappeared. She reached in deeper and I felt a sudden shock pass from ass to my balls. I gasped in response. She pulled her finger out and I asked.

“Did I hurt you.”

“No, it just gave me a shock.” I replied.

She reinserted her finger and massaged me. She curled her finger as if making a Come Here gesture. The discomfort soon went away. She inserted another finger, keeping still and giving me time to adjust. I nodded to her when I was comfortable. She now started to move her fingers in and out. I decided it wasn’t too bad.

With her other hand she reached for my cock and started to stroke up and down my length. She picked up the pace with both hands and after a few minutes she lowered her mouth to my cock. The change to sucking took my mind off what her finger was doing in in my ass. My balls soon tightened and I gushed into her mouth. As always we kissed.

We parted lips and she said.

“I’ve always wanted to do that.”

I acknowledged that it was Ok.

I never asked her to do it again and she didn’t except for one time I was fucking her pussy and she slipped her finger into my ass. It put me right off my game.

[thegrayprincejt]

My first actual anal experience, besides analingus, was actually my 21st birthday present. My girlfriend at the time was a very slender and flexible girl. She enjoyed all sorts of kinks and was always teasing me about my love of eating her ass.

Night of my birthday we we're at a friend's house watching movies. She was wearing a skirt and sitting in my lap under a blanket. Next thing I know she shifts a little and unzips me then starts stroking me slowly and teasingly. After I got about half hard, for the third time, she slipped out from the blanket to go use the bathroom.

When she came back she grinned and started stroking me again...only now she had her very damp panties wrapped around my shaft. She whispered in my ear asking if I wanted a sneak preview of my birthday present. Of course I said yes. She eased over and buried me in her pussy and slowly ground her hips against me. I was in heaven with her muscles working on me while our friends were watching the movie just a few feet away. Then she eased up, without saying a word, reaches back and holds my cock straight up, before pressing back and down slowly.

My mind went fuzzy because I felt the clench of her spinchter muscle. Slowly she wiggled and sank until I was fully buried in her, both of us breathing a little heavy. She put her head back on my shoulder and nibbled on my ear before whispering in it. "Happy Birthday sweetheart, just enjoy the feeling, get used to it. Tonight....you can have my ass however you want."

[Mark_2000]

After searching through boxes in storage over the last couple of nights. I managed to find and old photo of Leanne. I snapped it one night as she lay in bed reading a book.

Can’t remember what she was reading, however she was totally engrossed in it. I tried to distract her as I started to nuzzle her neck. She ignored me. I ran my hands up her thighs and started massaging her ass through her dress. She looked at me with the “Oh if you have to.” look and returned to reading. Not being put off I slipped my hand up and massaged her inner thighs, she readjusted her position to open her legs a little wider. Emboldened I started to rub her pussy through her panties. She put her head back and moaned a little.

I now pulled her panties down her thighs, once they were clear of her legs I moved in and started to lap at her pussy. She grabbed me by my head and pushed me into her. I reached up under her dress and found her breast. I gave it a gentle squeeze before pinching her nipple between my thumb and finger. This always stimulated her and she responded by moaning. She removed a hand from my head and started to rub her clit. I inserted two fingers into her pussy and thrust them in and out. I dropped my gaze to her ass and started to tongue her asshole.

She rolled over and hopped up onto knees to enable me better access to her ass. I continued to rim her deeply for the next couple of minutes. I thrust my fingers back into her pussy as she continued to work her clit. I removed my now moistened fingers from her and pushed them into her ass. I slipped my stiffened cock from my shorts and rubbed it up and down her pussy lips. She pushed back against me and I soon penetrated her. I continued to finger her ass. As our pace built she soon shuddered as her body climaxed. With that she fell to the bed causing me to slip out of her.

While still lying on her stomach I reached up and clasped open her ass cheeks. I quickly grabbed some lube, squeezed some onto my fingers and massaged it in to her asshole. I moved up and entered her ass, she moved her ass back into me. I stayed still as she continued to thrust back into me. Losing patience I started to move in sync with her. We continued with this for the next few minutes. Wanting to liven things up, I slapped her ass a few times causing her to get more excited and thrust back harder.

With my orgasm near I pulled out of her. She rolled over and got up and pushed me down onto my back. She turned and straddled me, now facing my feet she manoeuvred her ass back onto my waiting cock. I really enjoyed the view as she raised and lowered her ass onto me. I don’t know why we had never done this position before. In no time she had built up the pace. I grabbed her hips and thrust up into her to deepen the penetration. With her hands on her hips she was now bouncing up and down on my cock. I removed my hand and gave her a few hard slaps on the ass. This sent her into overdrive.

Needing to slow the pace I reached up and grabbed her, pulling her back towards me. Her back now rested on my chest. With this break to momentum my balls relaxed. With the change in position her movements changed. She now started to swivel her hips around my cock. I massaged her breasts and as her head lent back I kissed the nape of her neck. After a couple of minutes of slow fucking, the pace again quickened. I was soon thrusting into her ass with all my strength. She responded by rubbing her clit. She soon demanded that I fuck her harder. Not wanting to delay my gratification any longer, my balls contracted as my orgasm pulsed into her. She continued riding me and soon was embraced by her own orgasm. We lay in that position for awhile until my cock slipped from her ass.

She rolled over and hugged and kissed me. After a few minutes she reached for her book and started reading again.

It was the only photo of her I could find.

Sorry had to blur her face to protect her identity.

[Mark_2000]

By years end we had been dating for nine months. Leanne graduated and was offered a great job. Only problem was that it was in the next state at least a 4 hour drive away. She was excited about this new chapter in her life. I helped her shift to a nice studio apartment near the beach. After getting her settled we walked down to a local takeaway and bought some fish and chips. We went down to the beach and ate dinner. The full moon rose just after dark and we marvelled at its beauty as its light was reflected off the waves. Once finished we lay back and looked up at the stars. Leanne broke the silence.

“Let’s go for a swim.”

Me being my ever practical self replied.

“We can’t, we’ve just eaten.”

“A walk instead.” As she grabbed my hand. We walked and she lent into me as her arm hugged at my waist. We stopped and kissed. Her hands were soon stroking me through my shorts. I responded and squeezed her ass. Our lips parted and she said.

“I’ve always wanted to make love on the beach at night.”

“We can’t.” I replied with shock in my voice.

“Sure I can’t change your mind.” As she dropped to her knees, unzipped my shorts and took me in her mouth. I looked nervously around the deserted beach. Ok it was pretty hot getting blown in pubic out in the open. With the moonlight I noticed a couple walking up the beach. I pulled Leanne off me and pointed. She laughed, grabbed my hand and dragged me into the sand dunes with me clutching at my shorts.

“You know I always get what I want.” As she kissed me again.

Knowing she was right I relented. Feeling safer in the cover of the dunes. We lowered ourselves down to the sand as we continued to kiss. She stroked me until I was hard. Without warning she hopped up and quickly removed her panties from under her skirt. She straddled me and quickly inserted me into her very wet pussy. She rode me with increasing vigour. Anxious I soon came. She continued to ride me until my cock softened. She noticed that and changed her movements so that she was grinding her clit onto my pubic bone. Knowing she was near her orgasm I reached up to cover her mouth and stifled her scream.

Checking that beach was clear we both quickly stripped and ran down to the water. We didn’t go in much past our knees but delighted in splashing one another. Laughing I grabbed her and we fell into the water. We kissed as the waves washed over us. Cold and wet we made a beeline for our clothes and hastily dressed.

Back at her apartment we showered to warm up. We excitedly talked about our beach romp. After we got out of the shower I massaged her moisturising cream into her. Her back,bum and thighs got the majority of my attention. As I finished she turned onto her back and motioned me to her. I moved in and kissed her. She soon had me hard again with her hands. She raised herself up and pushed me onto my back. Her head traveled down and she soon had me in her mouth.

I laid back, closed my eyes and enjoyed the pleasurable sensations. I sensed her weight shifting on the bed. I opened my eyes in time to see her pussy move over my mouth. I started to lick her moist lips, I then inserted a couple of fingers into her pussy and stroked her. Once suitably moistened I moved my fingers to her ass and penetrated her. I massaged the back wall of her vagina. This caused her to increase her efforts in sucking me. Close to cumming I slapped her ass and ordered her to stop. She complained but complied with my order. She rose upright on her knees still straddling my face. I continued to give her oral and thrust my fingers in and out of her ass. Her hand moved down to her pussy. In no time my face was drenched in her juices as she climaxed.

She lowered her face to mine and we kissed. Still able to surprise me, she then proceeded to lick her juices from around my mouth. That was incredibly hot and she knew it. Just that action alone had me hard again. She then crouched over my cock and stared into my eyes as she lowered herself down, my cock entered her asshole easily. She now started to move her asshole around my cock. She knew this was my favourite view. She further excited me when she reached down and inserted two fingers into her gaping pussy. She now started to ride me as she continued to thrust her fingers in and out of herself. I grabbed her hips and thrust up into her.

The feeling of my balls tightening caused me to grab her ankles and sudjdenly lift them. With her hand otherwise occupied she was unable to steady hersnelf and toppled off me with her feet in the air. I laughed. She pouted. I moved down and kissed those beautiful lips. I moved my lips down her body and was soon licking her pussy. She let her intentions be known as she reached behind her legs and pulled them up to her chest. With her asshole presented to me. I quickly started to rim her deeply as I rubbed her clit. She started to rock her hips backwards and forwards.

As my tongue tired, I got up on my knees and entered her ass. She continued to rock her hips as I thrust deeply into her. With our momentum building I started to rub her clitoris. After awhile she took over on her clit. I grabbed her legs and raised them so her feet rested on my shoulders. Holding onto her hips I continued to penetrate her with a greater depth and pace. As she came her ankles locked around my neck. I had to slap her ass hard to get her to release her grip. I continued to pound into her hard as she begged for my cum. In no time I delivered a load into her ass.

I stayed with her for the rest of my holidays. I got a job at a local cafe and we happily cohabitated for the remainder of the summer. We happily fucked morning and night.

It came time to return home and start the new year at university. I tried to get down to visit her most weekends. Overtime with increasing study commitments I found it increasingly more difficult to find the time to visit her. Friction soon began to develop in our relationship. She accused me of seeing someone else as to the reason for my lessening visits. I had little luck in reassuring her and our sex life cooled considerably. Finding it increasingly more difficult to maintain a deteriorating long distance relationship. In the end we broke up. She was heart broken and I felt awful.

We did phone each other occasionally. Eventually we moved on and started seeing other people. With that she was gone from my life.

[Mark_2000]

My biggest regret apart from breaking up with her was that I never got to photograph her nude. I have only been served with my memories of her.

After looking on the Internet I found these old images of this girl, closest as to how I can remember Leanne as.

Different face, same hair. A very similar slim figure. The breasts are a close match in size and how they hung. Leanne’s ass was probably a little bigger and her bush thicker.

Overall a close match to how I remember her.

The first pic is my favourite. I can imagine Leanne looking over her shoulder and saying to me.

“Come fuck my ass.”

Ah, memories.

Anyway thanks to everyone who followed me on this journey down memory lane.

I hadn’t really thought about her for a few years. Now I realise how much I really miss her. She was obviously the best fuck I have ever had.

My next girlfriend wouldn’t do anal or role play, in fact she wouldn’t do about 70% of what Leanne did. Needless to say the relationship didn’t last.

The following girlfriend was receptive to ass play and after a few months we did anal. She wasn’t overly thrilled at first but got more into over time.

Leanne was the only girl who offered to do anal, without me having to ask. She was also the only girl who really loved it and orgasmed on it.

I sure miss her. At least I have my memories. For now at least. When I’m too old to remember I can come here and read about it