Ann Analized
Copyright© 2026 by domhp
Chapter 2
Erotica Sex Story: Chapter 2 - All my fantasies have a grain of truth, well several grains. This one very much so, but very much an erotic fantasy about a hiking friend. I can wish right? I am OLD, but still very active especially my imagination. I would love to hear from you once you have read my fantasy. You just might spark another story.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Heterosexual Fiction Cheating DomSub Anal Sex Analingus Double Penetration First Sex Toys Squirting
I had left the front door open all morning, just the glass storm door closed. I glanced up when I heard a car stop out front. I walked naked to the door to watch Ann get out of her car. I used my phone to video her quick walk up my front steps. She stopped outside the door and I told her to take off her ‘Make Love Not War’ shirt because we were going to fuck and she did not need it.
She looked at me, paused, then drew the t off and dropped it. I motioned her inside. Once she was in my hallway, she stopped in front of me. I was checking her out for the first time. Small breasted, but with pencil eraser nipples and very large dark areolas. Her stomach was flat and ended at a totally bare pussy.
I smiled and told her she was beautiful and needed to be on her knees. Ann knelt.
As Ann knelt, she too had been studying Will. As she rested on her knees, she looked across at his engorged penis. As he stepped up to her, she realized how much bigger he was than her husband. She used her right hand to lift his cock and she leaned forward kissing the tip and opening her mouth, took the head. Glancing up, she saw Will smiling down at her. She felt his hands on her head as he pushed himself deeper into her mouth. At about half way, she felt herself gag as his cock reached the back of her throat. But she just sucked harder and concentrated on holding his cock in her mouth.
I slowly pumped in and out of Ann’s mouth, luxuriating in the feel of her mouth on my cock. I marveled at her sucking and willingness to have me fuck her mouth, trying to get as deep as I could. Saliva drooled down her chin, but she even managed to make repeated eye contact. After over a minute, I withdrew, helping Ann to her feet.
I leaned down, kissing her, driving my tongue into her mouth, as she sucked and then dueled tongues. Breaking the kiss, I whispered: “You are quite a woman and deserve everything I am going to make you do, but I do want you to keep count of your orgasms and tell me the numbers as you experience them.”
Sucking Will’s cock, having him try and force it down my throat, had me choking and gagging, but I could also feel my pussy juices running down my thighs. When he stopped, he helped me stand, kissing me. I sucked on his tongue and gave him mine. He told me I was beautiful and that I was to count all my orgasms.
He then took my hand and led me through his house and outside on his deck. The deck looked out on his backyard and detached garage. Behind his house was a white fence. Junipers shaded the deck and provided a modicum of privacy. He had me sit on a chaise lounge as he knelt in front of me. Pressing my legs apart he buried his head in my pussy. His tongue slid deep into me, setting off my first orgasm. As I groaned out “ONE”. He began to lick my entire slit as I gushed. The sound of his sucking up my juices turned me on even more.
Lifting my legs, he pushed them up and out until his tongue could reach my anus, which be began to include in his licking. When his tongue began to probe my ass, I came again, squirting even harder across his face as I groaned loudly: “Two!” I expected him to back off as I drenched his face, but his tongue pressed deeper in my clenching ass. His nose was massaging my clit.
Withdrawing his tongue from my quivering ass, he licked upward until his tongue encountered my protruding clit. A flick of his tongue was followed by his mouth engulfing my clit and sucking it. I thought I was going to rise off the cushion as my whole body went rigid, my orgasm continuing as wave after wave of orgasm washed over me. His teeth clenching my clit, caused me to shudder and he stopped.
When Will looked up at me, my moisture dripping from his beard, he grinned and gasped: “You weren’t kidding, your pussy is a veritable fountain, your juices delicious and your clit is jutting like a little penis. And your ass is oh so sensitive and going to enjoy my cock.”
All I could do was continue gasping and grin. He pulled me up, took my place on the lounge cushion. “Cowgirl” he said as he pulled me forward straddling the lounge until I could begin to lower myself onto his cock. I did so slowly, adjusting to a girth, even bigger than my dildo.
“I love your sopping pussy, no need for lube,” he groaned out as I squatted on his thighs, feeling him fully embedded in my stretched pussy. I leaned over him, until we could kiss, his tongue snaking into my mouth, which I sucked with relish. I realized that I was tasting myself for the first time. When we broke the kiss, neither of us had moved, but I could feel his cock pulsing against the walls of my stretched vagina.
I made eye contact and gasped out: “You fit! Nothing this big has ever been that far in me. Thanks for waiting for me to get used to being so stretched.”
Will smiled up and said: “Any time you are ready, start moving, this fuck will be at your pace, the others not so much.”
Using my legs with my feet on the deck I rose slowly feeling every inch of his cock rub my walls as I rose. Feeling his cock head, I stopped and began to settle back down, luxuriating at the feeling of his cock plunge back stretching me and sliding past my G spot. My legs began to tremble, which I tried to ignore as I began to pick up the pace, plunging up and down on his magnificent cock. I was leaning forward, my hands on the arm rests.
Will lay motionless, staring into my eyes, except when I would reach the top of my stroke, where he would glance down at our coupling, watching his cock disappear back into me. I could not keep count of the number of times I rose and fell. As my legs began to give out, I started relaxing them and letting gravity drive his cock back into me. Finally, I felt another orgasm building, my entire body began to tremble and I collapsed down on Will, moaning out: “Threeee!”
Will was amazingly still rock hard. He drew my legs up, so I was kneeling on the cushion, splayed across his chest, panting. Grabbing my ass cheeks, he began to piston slowly up and down, in and out of me as his hands gripped my ass. I was still pulsing from the orgasm as his motions increased. His right hand slid across my ass and I felt his finger slip between my ass cheeks to where his cock was sliding in and out of me. Moistening his finger, I realized that he was about to insert it into my rectum. A loud groan emitted from my lips as I felt his finger slide deep into my rectum until I could feel it pressing against his pistoning cock. As both impalements began to speed up, I lapsed into my fourth orgasm. Barely whispering into his chest: “Fourrrrr.” My body felt like quivering jelly, my bones were gone. All I could do was lie splayed across Will’s chest pulsing with pleasure as my orgasm washed over me again and again.
I was still hard, my cock and finger deeply nestled as Ann collapsed on my chest. I could feel the hardness of her nipples poking my chest. We rested until her spasms subsided and her breathing returned to normal.
I used the arm rests to pull us up until I was sitting up with Ann squatting across my lap still impaled on my cock. My lap and the cushion under me were soaked from her juices. Her legs trembled slightly as I withdrew my finger from her ass. We kissed.
I helped her off of me, my cock popping out, to which she groaned. I had her turn around, telling her to bend over and put her arms out to the railing.
“My god, you want more?” Ann squeaked. Will moved my legs more apart and drove his cock back into my pussy. As he bottomed out, the force drove me forward, but he caught me with his hands and began to slide in and out of me. He began to pick up speed, pumping harder and faster. I could feel another orgasm building. Suddenly I felt what must have been his thumb, which was bigger, plunge deep in my ass. I groaned loudly: “GODDDDDDDDDD!” as I felt his cock begin to pump semen deep into me.
“FIVVVEEEEEEEEE!” I screamed as my entire body spasmed and coursed with wave after wave of pleasure. Another gush of moisture squirted out and ran down our thighs. I glanced down to see the puddle form at our feet.
I finally slipped out of Ann’s pussy, pulling her back until we could collapse onto the lounge. She nestled against me, her head on my chest. Our breathing slowly returned to normal. I said: “I think we need a shower and I may have to hose off the deck. Ann laughed, but stayed splayed along side of me. We may even have dozed off.
In the shower Will took great pleasure in soaping all my nooks and crevices and his cock began to stiffen as I cleaned his cock with my mouth. Soft I could take all his length and swish it around in my mouth, but as it lengthened, I coughed when it probed my throat.
“I think we’d better stop,” I said as Will’s cock bobbed in front of my face after my coughing. “I know I am too sore for anything else.”
I turned the water off and helped Ann out of the shower, drying her off as she did me. I slipped on shorts and a t-shirt. I retrieved Ann’s t-shirt and told her we were going out for lunch. Pulling on the lone shirt, Ann looked at me questioningly. I just handed her some flip-flops and putting my arm around her, pushed her out the door. We walked down to my SUV. I drove us to my favorite sub shop, handed Ann some money and told her to go in and pick up an order for Will. Amazingly she complied and scooted out the door and into the shop in nothing but the t-shirt.
Blushing profusely, I walked into the sub shop, feeling everyone’s eyes on me and knowing they knew I was naked under my shirt. “I’m here to pick up an order for Will, please.” I stammered. The young kid smiled broadly and handed me a bag with a cheese steak.
Back in the car, I was still blushing as I climbed in and belted up. Will grinned at me, knowing how uncomfortable I must have been. I smiled back. We drove to a park next to a dam. Will spread out a blanket and we ate our sandwich and drank cold Yinglings. Fortunately, there did not seem to be anyone around, which was good since I had trouble keeping my bottom covered.
When we were done lunch, Will drove us to a sex shop, called Bend Over. Inside he told me to pick out a butt plug and lube, saying: “If you have any questions ask the salesperson.” I began to wander the isles, determined to not have to ask a question. Finally, I found a labeled butt plug which I thought was about the girth of Will’s cock. At the display of lubes, I read until I found one that said it was recommended for anal sex.
When I carried them to the counter, I could feel myself blushing from the tips of my toes to the top of my head, but my pussy was sopping and my thighs dampening. The saleslady asked if that would be all and laughed when I croaked out a yes. Will paid and I was relieved when we got outside.
Once in the car, Will asked if I had ever fucked outdoors. I must have looked shocked, because he laughed and before I could say I did not have shoes, he reached into the backseat and handed me some sneakers and socks, saying: “Bev’s”.
We drove into the countryside to a seemingly secluded parking lot. Will carried a blanket into the woods until we came to a pond with a tree shaded grassy area. We spread out the blanket. Will asked me to practice my deep throating. I looked around nervously, undid his shorts and released his cock. Taking it into my mouth, I pushed myself down his shaft as far as I could, coughing I backed off, looking down at where my hand gripped his erection, I had taken just over half. Will smiled and told me to try again. I could feel my own juices flowing as I sucked his cock back in my mouth, pushing down until I could feel him in my throat. My eyes watered, saliva drooled, as I continued to suck and push deeper. Suddenly he erupted and I could feel cum pumping into my mouth, swallowing made him groan and me squirt myself.
Will’s hands captured my head, keeping his softening cock buried in my mouth. I continued sucking and swishing my tongue around his cock. Glancing up, I looked into his hugely smiling face. “Six,” I gasped, swallowing again and smiling back.
“Congrats, my cock whore, a most successful deep throat and on only the second try,” he stated.
“But you definitely postponed your anal deflowering until tomorrow, as I am going to need time to regenerate.”
Will released my head and helped me stand. I looked down at my thighs, which were glistening with dampness and there was a wet spot on the blanket. We kissed, gathered up our things and walk arm and arm back to the car. Will deposited everything back in the SUV.
When I opened up the passenger door, Will came up behind me and told me to bend over. As I did, he reached over me, picking up the plastic bag that contained the items I had gotten at the adult store. He told me to spread my legs further as he lifted my t-shirt, exposing my backside. I heard him tear into the plastic cover off the butt plug, causing me to tense. Suddenly I felt him begin to rub the blunt end of the plug, not at my ass, but along the folds of my damp pussy. Once the end was damp, he slowly pushed it up into me. The plug began pumping in and out of my pussy. I could hear the squishing sounds it was making. Will must have knelt because the next thing I felt was his tongue probing my asshole. I surmised that he was preparing to insert a naturally lubed butt plug into my virgin ass. His tongue wormed and licked; I could feel his saliva dripping from my ass. My entire body began to vibrate. The feeling of his tongue probing such a forbidden orifice had me shaking, but the anticipation of his trying to push that plug into my virgin ass had me trembling.
The pumping stopped; the tongue stopped. As he withdrew the plug he leaned over and asked if I was ready. I nodded my head and tried not to tense. I felt the blunt end of the plug touch the tight ring of my anus. Slowly Will began pushing, as the plug forced its way into my ass, a dull pain began to grow. I tried to stay relaxed, but as the pain increased, I couldn’t. When Will felt me tense and heard me groan, he stopped pushing. I breathed deeply and leaned my head on the car seat. I gave a muffled plea: “More please, but keep it slow.”
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