Long Journey To Cuckold Life

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Section 1

When I was a freshmen in High School, we moved to BryXXX Ohio. My dad got a promotion at a Toledo Ohio Glass company. As we moved in We met our new neighbors Bill and July and their teenage daughter Sandy. Sandy was my age and a pretty brown haired with big teenage tits. My first night in my new bedroom on the second floor I could see into our neighbors house and Sandy’s bedroom. No I didn’t see Sandy naked that night but I did watch her move around and the lights go out. I jacked off twice that night thinking of Sandy and her big teenage tits.

Sunday came around and Sandys’s mom and dad invited us to church and my dad said that would be nice. Sandy sat with her friends and I sat with my parents but I kept looking at sexy Sandy. After church Sandy’s mom invited us over for dinner, I was happy to be able to spend time with Sandy, we became friends right off. After dinner she showed me around the neighborhood and where the school was. That night I looked into Sandy’s bedroom and saw her get undressed – couldn’t see much due to the curtains but I had to jack off 2 more times before I could go to sleep….Looking into Sandy’s room and jacking off every night became my routine.

When school started up Sandy showed me around and introduced me around and I met David… Sandy’s boyfriend. I was heartbroken to find she had a boyfriend but actually liked David and we became friends. David was on the football team and asked me to try out. I did and made the team as a 2nd sting receiver – David was the QB. I was making a lot of friends on the team and David made sure when I got in the game he would throw me a pass, I even scored a touchdown in our 3rd game. Sandy was a cheerleader and I loved to watcher her cheer, her tits and sexy ass were so hot in her cheerleader outfit.

Sandy’s dad didn’t care too much for David since he wouldn’t come to church, but David treated Sandy with respect in front of other people and that made Sandy’s mom and dad happy. One day Sandy’s mom and dad were out of town for a funeral and I saw David’s car pull into the driveway, it was dark out and I saw Sandy’s bedroom light come on. Then I saw Sandy and David kiss/making out then I saw him take her shirt and bra off, I have my 5.5 inch cock out and was rubbing it as I watched (This is where my cuckold desires started). I saw David licking and sucking her tits then all of a sudden Sandy got down of her knees.. I couldn’t really see it but I knew she was giving David a Blow Job.. a few minutes later his head went back and I could tell he was Cumming and I shoot my load too. They then walked out of Sandy’s bedroom and a few minutes later David drove way.

In the locker room David was talking with a few of our friends and David said Sandy was a good girl – The guys said ya but I bet you fuck her brains out and David said HAY man knock it off I love Sandy and she is a good girl…I knew Sandy was a good girl that sucked HIS big cock and I was a bad boy who jacked off thinking about her sucking HIS cock and HER eating his CUM. This went on for the next 3 years of High School. One day Sandy told me a few secrets as she said I was her best friend. She told me that her and David were lovers and she loved his 9 inch cock.. I said too much information Sandy and she laughed and said well I know a secret about you and I said what?? She said I know you look into my window and then jack off… I was mortified…Sandy laughed and said its ok you are my best friend. I was red and embarrassed. Then Sandy asked me if I would do her a favor and I said Sandy I would do anything for you..She said Ok I’ll call you tonight and ask you.

About 10:30 that night she called me and said will you do me a favor and said YES Sandy what do you need. She said look out your window..There she was naked looking right at me.. She said Stevie will you please jack off while I watch?? I said what are you crazy. Sandy Said Please Steevie I know you jack off thinking about me please Steevie Please I want to watch you jack off Please David won’t do it in front of me and I want to see a guy jack off Please Please - She said look at my tits and jack off. I was so Horney and she was so sexy and I could see her big tits and nipples, she pulled her nipples and I started jacking off, She said that’s it Steevie jack that little cock for me jack it sweetie then within a minute I shot my load.. Se laughed and said sweet dreams and hung up and shut her curtains.

The next day at school I saw her and her girlfriends looking at me and they started giggling and I almost died..Did Sandy tell them I jacked off for her…Later she told me NO she did not tell them they were laughing because they all know I had a crush on Sandy. A few week later after church Sandy asked if I could help her with some homework. I went over to her house and her mom and dad were gone. She then said she wanted to watch me jack off right in front of her – She took off her tee shirt and said If I did I could suck her tities after I came… I didn’t want to but Sandy said Please Steevie please let me watch you play with your little cock Please.. So I took it out and she smiles as I pulled and tugged..

She said David’s cock was twice as big and she loved they way it felt.. she said my little cock was pretty… She then said stroke Steevie stroke it and when I was about to cum she said CUM on my tits Stevie cum on my tits and I did.. She laughed and said David cums about 3x more but mine was white and hot. Then Sandy said OK little stevie now I want you to lick and suck my tities and lick your cum up for me… I said NO way.. She said YES you will and YOU will do it now or else I will tell all the girls at school about your little cock and how you jack off in the window each night..Sandy said ohh Stevie please I love David’s cum its not bad please Stevie lick your cum for me… I did and it tasted groos ..

Sandy Laughed and said she loved me and I was her best friend. Sandy kept me jacking off for her and made me eat my cum every time and I actually started to enjoy it. Then one the night before our senior prom she called me over and we were in her basement. She asked me to eat her pussy. This was the first time and I said YES… As I did she was sooo very wet and kinda tasted sweet but also like my cum. When I was done she had cum2 x then she asked me if I like her pussy and I said YES it was wonderful and the she asked if I liked eating David’s cum in it…I said what you had his cum in there ohhh Sandy why did you do that.. She laughed and said well you just told me you loved it so what’s the problem?? I felt sick and then she said she wanted to show me she loved me and she would jack me off… She took my cock out and said its so pretty but it is so small. As she jacked me off she looked in my eyes and said I love you Steevie and I shot my load all over her hand. She then feed me my own cum and then she kissed me with a deep French kiss and said Stevie you are my best friend and I love you Thank you.

A few weeks later we graduated and started to get ready for college. David got a scholarship to play football to a big college in Missouri, Sandy was going to Michigan so they decided to break up. My dad got me a job at the glass factory and I was going to go to the community college. Sandy would call me about once a week and tell me who she was fucking and how she loved there big cocks etc… as I jacked off for her over the phone. She slowly stopped calling and I didn’t see her or hear from her for about 6 months. She came home to visit and I introduced her to my girlfriend Carrie and she was so happy for me. Carrie was my new girlfriend and Her and Sandy were fast friends. A few week later Sandy had me come over for a talk and she told me she was so happy for me and Carrie and she wanted me to know she still loved me and thought of me as her best friend. She then kissed me good bye and headed out back to college.

I hadn’t talked with Sandy much over the last 3 years. I was graduating from college as so were Sandy and our old Friend David. Our families decide to have one big party for all 3 of us. At our Party David met my girlfriend Carrie for the first time and asked me how I got such a little hottie… we laughed .. Latter there was dancing and David asked if he could dance with Carrie and I said I guess so and Sandy said come on Steevie please dance with me… Later David was dancing again with Carrie holding her close Then I saw his cock sticking out in his pants and Carrie has rubbing it with her hips.. I got a hard on watching.. My mind was running wild and I thought what if David wanted to fuck Carrie.. then in my mind all I could see is Carrie sucking and fucking David and HIS 9 inch cock.. I was awaken out of my Dream as David said thanks buddy Carrie is a great dancer.. Carrie sat down next to me and she was all flushed. She didn’t say much to me that night and didn’t even give me a kiss goodnight.

The next day I saw David’s car in Carries driveway. I parked down the road and got to the side of Carries house and looked in the window and almost fainted when I saw Carrie on her knees sucking David’s big 9 inch cock Then She got up bent over the couch and David Started fucking her doggie style. I was as hard as a rock as I watched and shot my load.. Then David Pulled out and shot is load in Carries mouth and all over her face… I turned and ran to my car and drove home… at 6 pm Carrie called and said she wanted to brake up with me and I said I understand I guess YOU loved David’s big 9 inch cock more then me and I hung up. 3 hours later Sandy Called and said David told her about him and Carrie and He said Carrie told him I knew about it and He told Sandy to tell me He was sorry. I never talked with Carrie or David again.

Three years later I ran into Sandy, She was still so beautiful. She hugged and kissed me and said she loved me. I asked her to dinner and she said yes but not until Saturday. We met for dinner and Sandy smiled at me and said Steevie since the other night did you jack off thinking of me… I turned RED and said yes yes I did..She laughed and said good I’m so happy you still love me. After dinner we talked for a while and she said she had a great job and made great money. I told her I worked at the glass company. We started having dinner about 1 x per week and soon Sandy asked me to give her oral pleasure and I was happy to do so. One night she called and asked me to come over she needed me to please her. As I went down on her I knew it was her pussy juice but also some guys cum.. she laughed and said please Steevie eat me till I cum and I did. This went on about 3 or 4 days a month for the next six or eight months.

Section 2

One night after I licked her cum filled pussy clean, Sandy said she had something important to ask me. I said Ok sweetheart what do you need? Sandy said Steevie you know I love you right? I said sure I know you love me and you know I love you too. Sandy said Stevie will you marry me?? I said wooow you want to marry me??? But that would mean you would be faithful to me and have to give up your boyfriends and there big cocks! She said YES Stevie I am willing to do that, I have had my fun and I love you and want to be your wife. I said that if you love me and are willing to be faithful to me and love me and my little cock I would be happy to marry you..That night was the first night she allowed me to fuck her with my little 5.5 inch cock. We told our families we were getting married and started to plan our wedding and honeymoon. Sandy stopped seeing her other guys and told me I was her love and she was so happy

A few months later, We were to be married in a few weeks and David was to be my best man (NOT MY IDEA but Sandy’s). He threw a bachelor party for me and HIS friends not mine and had a sexy stripper for us..To my surprise it was Carrie my old girlfriend. David had made her come and strip for us.. David then made her give him a blow job in front of everyone. When they were done I said David that’s not cool I then walked out and went home. I called Sandy and told her what David had done and she laughed and said relax, that bitch Carrie deserved it for what she had done to me. The morning of our wedding David met me for breakfast and said he was sorry for the party.. He said Carrie is a wild lady and wanted to show off in front of me and his friends..But David said he was sorry it upset me and he would be on his best behavior from now on. The wedding and reception went off without a hitch everything was wonderful and Sandy and I had a wonderful honeymoon with lots of sex and fun times…That was 10 years ago and that brings us to now.

Sandy found out she was not able to have babies due to an issue and surgery she had when she was 10 years old. We had been trying to have a baby for over a year. This really upset Sandy and our sexy life started to drop off to almost nothing. After a few months I talked with her and Sandy said she was sorry and that she would try to do better. We did start having sex again about 1 x per week… It was not great she hardly got into it. After a few more months of less then great sex we talked again and she said she loved me but fucking me was doing nothing for her as my small 5.5 inch cock didn’t hardly cause any feelings but she said she loved me and I could continue to lay on her and fuck her 1 x per week. This again went on for a few months then one night Sandy said stevie why don’t you just jack off tonight.. I did then she told me to lick up my cum for her and I did then she got excited and told me to lick her clit and I did and she came hard… We hugged and kissed and I thought she was getting her passion and love for sex back. This went on for the next year…me licking her to the BIG O, me jacking off onto her toes, tits,belly and or ass then ME licking it up and then us kissing and hugging. NO actual fucking now for over a year.

I was now VP of Procurement at the Glass Company. I was making great money and got a big bonus every 6 months. The downside of my job is that I had to travel about 5 nights per month. Sandy had just Taken a new position at a non profit organization dealing with Kids with medical issues. Sandy was their new director of Fund Raising. Her job was considered part time about 20 hours a week but the downside was that once a week she would need to host fundraising dinners with local doctors and hospital’s. Her boss was Doctor James, He was in his mid forties 6’3” 200 pounds and was a former college tennis player… I was intimidated by him as a man’s man and Sandy loved working with him and couldn’t say enough about how wonderful he was and how he cared so much for the sick children and their families …. I thought in my heart that Sandy had the hots for him and in my mind I knew his cock would match the size of the rest of HIM. I attended some of these dinners but Sandy started saying I should just stay home and relax, NO need for me to be bored at these dinners. So I started staying home. I would watch my LOVE Sandy get all dolled up and head out..for her job??? Or was it for for Doctor James????

One night in BED Sandy said stevie sweetheart can we talk..I said sure baby what’s up?? Sandy was hesitant but finally said she missed fucking… I said so do I baby..Sandy said NO baby I mean I miss fucking a BIG cock you know a real MAN’S Cock…She said stevie I love you with my whole heart and since we have been married I have never cheated on you…But I have been thinking I need to fuck a guy – A MAN with a BIG COCK… I said with tears in my eyes Ohhh Sandy, well I guess we can get divorced and you can do as you want and need…Sandy said NO stevie I don’t want a divorce, I want your permission to take a lover from time to time..

Sandy said she would NOT do it without my permission and she doesn’t want to lose me as she loves me. She then said she had some stories she wanted me to read about hot wife and cuckold and showed me the site cuckold consultant. She had picked out 10 stories for me to read over the weekend and she asked me to be open and think about it. I said I am NOT interested but since I love you I will read them..BUT I told her if she was unfaithful to me I would not forgive her and divorce her! She smiled , Kissed me deep then went down and sucked me off, something she had not done now in almost 2 years ( Only took about 2 minutes)

Each night for the next 10 nights I would read out loud one stories from cuckold consultant that she had picked out as we laid in bed together and she would rub my little cock… I would always cum before the end of the story and she would feed me my cum off her hand they make out with me until I was hard and then she fucked my little 4.5 ich cock (We had not fucked in over a year until then). On the 11th night she came in the bedroom in a garter, bright green stockings, 6 inch heels and a bright green see through baby doll nightie…She said Stevie I love you so much and the last 10 nights have been so sexy and HOT….She said Baby…will you allow me to cuckold you??? Let me fuck a man with a big cock??? Please baby, please be my cuckold husband???

I said Sandy I love you with all my heart BUT NO I will not allow you to fuck Doctor James or anyone else… She stormed out of the room came out of the bathroom a few minutes later fully dressed and told me to sleep in the guest room. We didn’t talk for the next few days…On Friday she texted me at noon and asked me to call her.. I called and she said SHE loved ME.. I said I love you too…When I got home she was dressed to the 9’s I said what’s up??..Sandy said Oh I have a dinner/board meeitng tonight.. She said she would be home late as they needed to get the board including Doctor James to sign off on the budget. She said baby I have some reading I need you to do while I am gone – She said she emailed me some things to look at.

After She left looking so hot and sexy, I opened my lap top and got her email… The reading were more cuckold stories… I got a hard on and started reading them…an hour later Sandy texted me and asked if I was reading and I said YES… She said good Stevie, good little boy..Sandy said But baby please don’t jack off and cum.. I want to show you I love you when I get home. She then sent me a link to a cuckold movie and told me to watch it while I waited for my hot wife to get home. The movie was a lady and her sissy small cocked husband. The lady was cucking her husband with her boss/co worker and they fucked in front of him then made him lick her cum filled pussy clean. SHE then made her small cocked sissy husband jack himself off in front of his wife’s lover as they laughed at him . I was excited, Horney and worried.. I was starting to think maybe Sandy should cuckold me..as long as she loved me..Oh man I really did want to be her cuckold… I must be out of my mind!!!… Do I really want her to fuck another guy???

At 10:00 pm she texted me a picture of her pussy…she said sweetheart I will be home in 15 minutes! Sandy said get naked, put on you garters, stockings, babydoll nitie and high heels..Sandy said tonight we are going to play hard my sissy cuckold…Well we had played like this before so I thought it would be just her and I and I was looking forward to being her sissy bitch. At 10:20 pm she walked into the bedroom where I was in my sissy outfit and ready to play. Sandy ordered me to my knees and asked me if I loved her and I said YES baby..Mistress yes I love you.. Sandy then said then beg me to make you a real cuckold, well I thought we were just role playing like we had done many times so I said YES Mistress please make me your cuckold.. She then ordered me to sit in the chair in the corner of the room. She then tied my legs and hands down like she had done many times during role play..Then she brought out a mouth gag..It had a 4 inch rubber cock that went into my mouth.. I had never seen this before. She then tighten it so I could not make a noise or move my head much..She then walked out of the room

10 Minutes later she walks back in with her own garter belt, stocking and 6 inch heels on..Man did she look sexy…Then she looked at me and said thank you for allowing me to cuckold you… I tried to say NO NO NO NO NO…even though I had said yes earlier I thought it was just our old role playing…NO NO NO NO I tried to say but nothing came out..SHE laughed and then said James please come in here and make love to me in front of my sissy cuckold husband…He walked in looked at me and cracked up then looked at my wife and said Sandy I have waited so LONG to make love to you..He took his clothes off and as she pulled down his boxers I saw his 9+ inch fat cock and Sandy sighed and looked at me and said..SEE sissy this is what I have needed not your little thing.

As I watched screaming into the gag NO NO NO NO with tears running down my face my wife Sandy started sucking Dr. James big 9+ inch cock. After 5 minutes of sucking HIS cock she looked over at me and saw I was as hard as a rock and she told Dr. James to look at my little boys cock and how excited I was and how I loved being her cuckold… They both laughed at me and got onto the bed and started making out.. I could hear every moan and heard her say she really needed him to giver her a hard fucking and HE said after seeing your little husband I guess you do. After kissing her neck, sucking on her big tits Dr. James made his way down to her pussy where he lapped at her wet cunt and sucked her clit to her 1st orgasm of the night.

MY wife Sandy and her new boyfriend Dr. James fucked on and off all night with me tied to the chair watching. Now even though I thought I didn’t want to be a real cuckold, I was NOW a real cuckold. It did turn me on watching My wife Sandy Fucking Dr. James. It did turn me on watching MY wife get fucked by a man with a cock twice the size of mine. It did turn me on watching MY wife CUM due to Dr. James BIG cock. All those things turned me on so much BUT they also HURT me so much as a man and Husband. The next morning after Dr. James left my BED & House, MY wife and I took a long hot shower where she held me and told me she loved me with all of her heart and told me she always would BUT that her and Dr. James would continue to see each other. She asked me if that was OK with me, I said I really didn’t know but for NOW I was NOW willing to be her cuckold as long as she was 100% honest with me and NOT play behind my back. Since that first cuckold night Her and Dr. James have played many times, sometimes at out house with me forced to watch and sometimes at his house without me. The following day my wife always makes sure she has time for me and so far Her and Dr. James have been open and honest me with.

With this being labor day weekend, Sandy and I had talked about going to a small cottage on Lake Huron near Tawas, Michigan. But on Wednesday night Sandy asked/told me HER and DR. James were going to Vegas for a LONG holiday weekend.. I was upset as it was a holiday weekend and I thought we had plans. Sandy saw I was upset and said she needed a good weekend away and she would make it up to me. I didn’t talk with her Wednesday night or Thursday morning or evening..Sandy Knew I was very updet with her!!!. Friday/ today when I got home from work there was a note on the table saying they were flying out at noon today (They were already in VEGAS as I read the note) and she would be home Tuesday morning..Sandy said I love you sweetheart and had a sexy picture of her in some new lingerie I had never seen.

So here I am home all alone, Sandys small cock cuckold, while HER and Dr. James are living the high life in VEGAS! YES I am truly her loving cuckold husband but it may be too much for me to handle.. It may be time to move on…If I do, I’m not sure it would really upset Sandy too much as I’m pretty sure Dr. James would not mind more access to my wife Sandy..Time will tell…..I am sure this is what happens to most real cuckold couples.

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