Moments of regret:
An Ana and Ian novel volumes 1 and 2
First allow me to state, that the events in this story are based off real life events, however some scenes may be exaggerated for dramatic effect. I am the character Ian and my wife is Ana, however aliases have been used in order to maintain the anonymity of some characters real identities.
Second I would like to clearly state that all characters are of legal sexual age, however there are some section containing under age drinking.
Ian had just started his first year of college. Being one grade behind Ana he had often visited her college. Now three months into this semester Ian found himself becoming aggravated easily weather over school or his family’s reaction to the announcement that Ana his girlfriend was pregnant with his child.
As Ana’s car headed down the path to Ian’s house they had been fighting, why or about what no one can be sure. He was young, naive, and wanted to be 18 and happy. She however was several weeks pregnant with his child and expected him to give up everything and focus on being a father.
Pulling up to his apartment she screamed and shouted at him, growing frustrated she said the words that would haunt them for years to come. “Get out, I never want to see you again”.
Ian did not wait, nor did he try to make a comment at her. He knew he was wrong, filled with anger yes, but still wrong.
He walked up to his apartment, no one was home. No one ever was. Although he did not live alone his roommate was always gone. He often joked that he lived alone, but being alone was not what he wanted tonight.
He wanted to be young, he call his closest friend and cousin Julie but she did not pick up so he dialed the next best friend Chance. Chance was known as the party guy. As well as a real ladies man.
“Chance, yes…. Um she broke up with me. I kinda just need to get her as far out of my mind as possible, can you and some friends come by?”
Within minutes his friends were on their way. First came Chance in a consoling manner he cheered up his friend with a nice half empty bottle of whiskey and an unopened 1 gallon bottle of vodka (The cheep stuff, of course). They started drinking shot after shot. After about finishing the whiskey and about 4 rounds into the vodka another knock came. This one was the girls Alex and Jo.
Alex was small, about 5’2 if that, she had red hair, bright red lipstick to keep the focus off of her small but still sexy chest. She hugged him and said it would get better.
Jo was short also, but not as thin as Alex . She was about the same weight as Alex but Jo was slightly taller. She was full Pilipino, with long dark hair she wore high up, and her nice full C breasts partial exposed by the sexy top she had on. Instead of a simple hug Jo guided Ian’s head midway from her shoulder to her breast; if she were any taller he would be motor boating her.
The night went on like any normal teen party (consisting of only 4 people). Drinking, pizza, stories, laughing….Then while Ian and Jo were talking they noticed the other two had gotten very quite, after a few minutes they realized what was going on. Alex was “pleasing” Chance. How exactly they couldn’t tell, but the soft moans and gasps of air implied either making out and a hand job, or more likely she was giving him head. Never the less they did not want to interrupt.
Ian took Jo by the hand and led her to his room, they sat on his be talking. Gossiping about how far the other two would go sitting there on his couch. He laid down on his bed, looking up to the ceiling. Jo laid on her side next to him, sliding her head on to his shoulder. She asked if she should stop the others before they ruined Ian’s couch. He said he didn’t care and readjusted his arm, laying his hand on her side. She looked up not sure how much was the booze or the fact he was pushing Ana out of his mind Ian leaned in for a kiss. What he got was so much more.
He lifted her shirt off revealing a lacy black bra. He thought for a second; had she worn this for him or was it just her partying fashion? Not wanting to ruin the mood while being in thought, he pressed his lips to hers and began passionately kissing her. Then with his right hand foundling her tits, he reached back with his left and unclasped the eye hooks holding it in place. Without stoping he moved both hands apart exposing her firm tits.
Jo realizing she was now completely topless looked at him with lust in her eyes. “I see you have some tricks up your sleeves” she laughed at him. He too had that same look. His right hand plunged into her pants undoing the button and loosening the zipper from pressure alone. His middle and index finger found their way to her tight wet hole and began to explore.
She was trimmed, not shave, but nowhere remotely close to being considered hairy. She moaned as he pushed his fingers in deeper. Taking this as his cue he pulled off her jeans leaving only a matching lacy thong. He pushed the thin fabric of to the side and went down on her nice pussy.
Licking her exposed clit he pushed two fingers into her stretching out her lips. Then after matching her hips rhythms he guided his middle finger to her tight rosebud. Her juices from her soaking cunt lubed her ass as he inched his finger in. She came instantly. This was something he always wanted to do with Ana but never was allowed.
With no word or warning she spread her legs wide allowing a second finger into her tight ass. Then she buck hard and went limp as she came twice back to back.
She sat up, with one hand pushed Ian to the bed and undid his button fly pants. No boxers just his stiff 8 inch cock stand upright. She went down on him viciously. Her tongue swirling around his shaft, he could see her lipstick shade on his cock showing exactly how much she was able to take at once. After going down on him for a few minutes trying desperately to take all of him at once, he grabbed the back of her head and forced her nose to his shaved pelvis. He held her there as she massaged his cock with he throat. He felt his cock begin to plump, anymore and he would have shot down her throat.
However he released her knowing full well they both wanted much more. As they began switching into doggy Ian grabbed a pair of handcuffs from his night stand. He had Jo perch herself on her elbows, and cuffed her wrists behind her neck. “Oh yes now we’re talking” Jo said clearly enjoying herself. “Give it to me” she cried.
He slid his cock into her now dripping pussy. As he began slow but full trusts he gave her a forceful slap on the ass while still feeling the sting he slid his thumb into her ass whole. She cried in sheer lust. He began picking up the pace trying to match her as she trusted back both into his cock and his thumb.
After what felt like a half hour that tingling sensation started to arrive. The one that tells you, your about to cum. Then like a sack of bricks he remembered they’d not used a condom and he already had Ana pregnant; he didn’t want a second pregnant girl.
“I hope your ready” Ian said as he switched his cock now into her ass. He was thick and she was tight. Even after being played with for so long he had to ease into her, as to not hurt her. Jo leaded back and began to moan. “You like my ass yes, stay with me and its yours every night.”
Her words sent him on edge. He quickened his pace and began thrusting harder and harder. Jo screamed slightly unsure of if it was pain or pleasure. Then he shot several globs of his hot thick seed into her ass. Jo’s ass tightened with each shot milking out the next. Once he was done and his cock started to soften, Ian pulled out, and grabbed the keys, un cuffing one hand she rolled over and began kissing and biting his chest, shoulders, and neck.
After laying in each others arms Jo playfully excused herself to the bathroom. After a few seconds she came back, her hair although still in a bun was frizzed, her makeup was ruined, and she had a goofy grin on her face. “Where’s my thong?” He didn’t remember taking it off nor did she. Ian rolled over to the side of the bed, there it lay. Ripped from there escapade.
They giggled and began to get dressed. While Ian was putting his shirt on they kissed one last time. He handed her a container of baby wipes and she slid back into the bathroom to reapply her make up. Stepping out her hair now down to her shoulders, “Let’s go check on those two.”
Alex was laying her head on Chance’s lap lipstick smeared slightly. “Sorry guys we didn’t even see you two step out.” Alex said. “Talk about whiskey dick, it took me a hour to suck him off” she whispered to Jo. Jo instantly looked at the clock it had been over a hour almost 2 since they walked out of the room, yes they had talked and cuddled but Ian clearly had stamina and skill.
Jo gathered Alex’s purse and told her it was time to go.
———–That Next Monday ——
While walking to Creative Writing. Alex came by slapping Ian with her purse. “You fucked Jo, are you crazy?”
Ian having not even seen her until she’d hit him. “Hey watch it don’t tell the world.” He said rubbing his arm. “Damn, what do you have in there?”
She looked him dead in the eyes, “whatever Is in here is nowhere near heavy enough. She kept me up all Saturday night talking about you guys were fucking while I was In the next room”.
This caused him to start to laugh. “You were giving Chance a hand job if not already a blow job while we were in the same room, hell at the other end of my coffee table.” She smiled in both a playful and slutty manner.
They took there seats next to each other in class. Professor Papis was still setting up the board. “Did he say anything about me?” She asked Ian.
“No, he went sleep on my couch, I went to my computer and started talking to Ana.” She looked at him dead eyed. “She pregnant with my kid, I can’t just give up.”
Part 2
———— 3 months later——–
Ana was in Ian’s bathroom crying on his toilet. “You asshole you cheated on me.”
“You broke up with me, I did not cheat on you. ” he said stern.
“I was mad at you so you go and cheat on me,” she sobbed ” I had just left not even a day before hand. I never broke up with you.”
Ian was clearly upset. “You said I never want to see you ever again. To me that means we were broken up.” Sitting in front of her holding her hand. “Listen it was a one night stand, and I told her the next time I saw her. I may not be the best boyfriend but I am a loyal one. And as far as loyalty I want to be the father of our child together by your side.” He reached into his pocket. “I clearly was waiting for a better moment, ” he took one knee and showed her the beautiful 3 piece diamond engagement ring and wedding band. “But if don’t do this now I feel I’ve lost you forever, I wanted to know if you’ll marry me.”
Her mouth damn near dropped out of its socket. She kissed him and put it on. “I’m still mad at you, but this is, oh my god, it’s amazing”.
——-5 months later————
Ana was an intelligent woman she recognised that her husband’s income could not support a family of 3. Even with WIC, her unemployed, cost of living, both student loans, and their apartment they weren’t event floating they were steadily sinking. She decided to move back in with her parents two states away. Then one day she asked not for a divorce but an annulment. Ian agreed and the paperwork began.
Not feeling guilty, he changed all his social media statuses to separated or going through a divorce. But he remained loyal still going on dates here and there maybe a kiss on the cheek but nothing more.
During the next 7 months they canceled the annulment as Ian had earned a hearty raise at work, but they lived separately still. Ana assumed Ian would have an affair if things carried on the way they were going – any man would.
———–1 year later————
After a year of being separated she moved back in with Ian this time in a two story small house. They were happy and a family once more. About a month went by when Jonathan a coworker came by asking for Amy.
Ana not knowing who Amy was had to inquire. “Ian’s girlfriend, who are you, I thought you’d be her sister.” Ana was furious.
“I’m Ian’s wife. We’ve been married almost 2 years now.” Jonathon quickly saw the anger in her eyes and left in a hurry.
That night Ian and Jake came to the house. After pulling the evening shift. They shared a few rounds and instead of Jake driving home Ana encouraged him to sleep on their couch. She had planed to get revenge this night and knew exactly how.
Hours later after Ian was fast asleep. Ana crept into the shower rinsed off and put on her best make up. Then ever so silently tiptoed down the stairs in her sheer teddy holding only a bottle of Astrogluide and tapped Jake on the shoulder waking him.
Jake lay in awe as he took in the sight of his coworker’s wife leaving little to his imagination. “I can’t sleep”, Ana said coyly. “Can you help me out.” She looked at his pants bulging at the crouch. Then glided her hand over the zipper. “Or can I help you out?”
Jake is a tall man 6’4 built like an ox. He stood a clear 1/2 foot taller than Ana. She undid his zipper and a huge 10 inch uncircumcised cock flopped out. She was shocked. Ian was big to her standards but Jake was just crazy.
She began to suck him hard which took almost no effort, although his cock had that taste of Winston cigarettes seeping through his skin. After standing the taste all she could, she flipped to top of the Astrogluide and coated his huge manhood. “I have no condoms, and I’m not on birth control so you’ll have to fuck me in my ass.” With that she lay over the ottoman. She turned her head slightly “Ian has been wanting my ass for years, and I’ve never given it to him” she smiled “guess you’ll get to pop this cherry!”
Jake slightly turned off by anal was so hot he could care less. However aside from a one time fling with the farm girl down the road Jake was rather inexperienced in the ways of sex. Ana although only ever slept with Ian until now, at least they’d been rather sexually active with Ian during their years together.
Jake grasped the concept of anal. Ease his penis inside. Then once she’s comfortable pick up the pace. Now grasping the concept and performing are two different things.
He pressed his fat cock head into her barely lubed ass and just went to town. He bucked as hard as he could. She quivered at the knees an began to pant and twitch as Jake’s cock just kept pounding.
She tried to brace her hands but it was no use he quickly picked up speed until she felt warm thick seamen inside her ass. Afraid to stand up thinking it may drip out she lay there.
Jake sat there stroking his cock looking at the half passed out wife in front of him. Then he was hard again. He walked around the ottoman to her face. His shadow over her head made her eyes open.
He took put one knee on the ottoman and stood planted on the other firmly on the ground. He moved her head to his cock and began to ease it into her. He was much gentler at this than the sex.
He made her suck him until he was fully erect the taste of cigarettes returned, only now mixed with the odd tangy taste of the lube. He walked back to her ass. “Please not my ass, your too big” she begged. He shifted her so that she flat on her back and buttocks, then worked his cock into her pussy. He fucked her roughly for 10 minutes not caring about her needs at all.
He would on occasion take one of his bear size hand and massage her tits but even still it was too rough for her. He shot his second and final load deep inside her pussy. Finally he finished she kissed his cheek and walk back upstairs.
She washed herself off in shower one last time. While in the shower Jake walked in his phone in hand and ask for a photo of her naked, she squeezed her tits together making them seem a size larger, put on a fake smile and let him take the photo. Then he left.
Ana dried herself off and wattled to bed. She began to cry. Not only had she failed at getting the revenge she though she wanted, she felt violate by Jake despite the fact she knowingly and in clear state of mind initiated it. And to make matters worse she let him cum inside her.
After several minutes Ian woke up to the sobs. “Are you alright sweetie “ He asked in his half waken state”
“Yes she said.” He pulled her close to him, batted her long hair out of his eyes and held her.
Come morning Ana woke up happy to be with her husband and unsure if it was a dream until she began to feel the odd feeling of pain in her throat and ass.
She leaned in to kiss her husband only to be stopped dead in her tracks. “Have you been smoking you smell like a pack of Winston’s?”
Not knowing what to say she froze then said “I
couldn’t sleep so I stole one of Jakes last night.” He pointed for her to go brush her teeth. Seemed kinda rude, but remembering the taste of Jake’s cock she couldn’t blame him.
Source: reddit.com/r/eroticliterature/comments/8b8uj8/moments_of_regret