Highschool Sweetheart - Pt. 03

Based in the comments, we combined parts 3 and 4. In this part, my wife starts to really explore her sexual freedom after a breakup.

My wife never rubbed her experience with Adam in my face. She only shared details because I was curious. In fairness to her, we were separated. 2) Our relationship was bumpy in our late teens. We were both young. Looking back, these experiences helped us grow. Keep in mind this before we committed to each other.

Thank you for reading and appreciate the comments

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My wife is stunning and always has been. Beautiful face with a athletic slim body, but gifted in the right areas. I dated/married up with her. She was always considered one of the hottest girls in highschool. She could have hooked up with any guy, at any time that she wanted. Even 22 years later, she's always getting eye-ball fucked wherever we go. What drew my to her was her beauty, bubbly personality, and high character. She is unselfish and loves to make others happy - even in the bedroom.

When she told me about Adam, I was so aroused envisioning her doing this. Post nut, I was jealous and envious that a big dicked 27 y/o asshole got to use my wifes body for his pleasure. Less than 6 hours meeting her, he had her beautiful mouth on his cock with her naked body on display. Her going to his house again confirmed that she enjoyed it and was attracted to him. Even though she acted slutty the first night, she wanted more and was willing to let this guy use her body for pleasure. She walked into his house knowing what she was there for - to let him enjoy her body and explore his big cock again.

It stung when I found out that she only stopped hanging out with Adam because he bragged about it. He told all his friends about her pussy and swallowing cum. After work one day, I made the mistake of asking: "What if Adam didn't brag about hooking up with you?"

Wife: What? Where did this come from?

Me: I don't know, but what if Adam had kept his mouth shut. Would you have went to his house the next day?

Wife: Umm, yeah I guess, until Sarah told me what he said to Greg.

Me: Would have had sex with him?

Wife: You want me to be honest? You might not want to hear this

Me: Please, be honest.

Her: Yeah, he would have expected it and I would have.

Me: Why did you think you moved so fast with him?

Her: I dont know honey. Maybe because he is older and assertive. It just happened. He was very forward.

Me: I still can't believe he put his cock in you

Wife: Sorry honey, it wasn't the plan

Me: If he hadn't bragged, would you have kept fucking him - like been fuck buddies?

Her: I guess. I really didn't like him - it was just a hookup.. There was no relationship potential there.

Me: So it would have just been fucking?

Her: I guess

Me: Sorry if this is too far, do you have any regrets?

Wife: Not really, it was just a hookup.

My mind couldnt let it go. The idea that if Adam had played his cards right, he could've fucked my wife everyday in every possible position. Adam was one slip away from having a 19 year old sex goddess on speed dial for his sexual pleasure.

We were working through this and even incorporated it into out sex life. We had been back together a month when the other shoe dropped that created a problem and ultimately a break up. Sarah was over one night and they were drinking wine. I was in the other room on my computer doing some work. I wasn't eavesdropping but I could overhear them. They were drinking and were probably loader than they thought. This is what I heard:

Sarah: is Mark fine with all the Adam stuff

wife: yeah, we worked through it. We were separated.

Sarah: you shouldn't feel bad at all. If I was you, I would have fucked Greg too. You saw the size of his cock

wife: ohh my god, you are bad

Sarah: what, I saw you guys in the pool. He was hard as rock after you swam away from him

Wife: I didn't know you saw that! I felt it against my butt (giggle)

Sarah: you little slut, l love it!

wife: I didnt do anything, but he did play with his boobies a little bit. He wasn't shy about letting his cock rub against me (giggle). That's why I swam away.

Sarah: Thank you for getting him all worked up for me

wife: You are welcome That was a crazy night

Sarah: Be honest, what did you think of his dick

wife: You mean "the coke can" as you call it. Its impressive

Sarah: Ohh my god, you should have made a move with Greg. He's not the douche Adam is. You would have loved it

wife: I thought about it, but he was yours

Sarah: You should've. I would've fucked Adam. Fucking Greg is like going on a Disney ride. The first time is scary and then you just want to keep doing it

Wife: What is scary about it?

Sarah: Try putting a coke can in your vagina. It's terrifying.

Both girls laughed

Sarah: Greg so wants to fuck you

wife: I'm unavailable, but thank you

Sarah: Then you shouldn't have shown him that hot body of yours. I didn't know you shaved

wife: I didn't know you guys were coming outside. Mark likes it shaved

Sarah: So did Greg and Adam! Did you see Greg staring at you when your were naked?

wife: I'm glad you all enjoyed the show

Sarah: Greg talks about you a lot. He is a great guy, with a big dick bonus

wife: Okay, but I'm back with Mark.

Sarah: Do you wish you had hooked up with Greg instead of Adam

Wife: I don't know, maybe, Adam is an asshole

I was hurt because I believed my wife's relationship with Greg was much more platonic. She had showed me their texts and there was nothing to indicate they had some level of intimacy. This was a hard way to learn that he had seen my wife nude and that she had seen and been touched by his penis.

I waited to Sarah to leave before confronting my wife. In retrospect, I should have slept on it. Once Sarah left, my wife came to see me and noticed I was upset.

Wife: whats wrong honey?

me: not much, you have fun with Sarah?

Wife: yeah, she's a riot

me: what did you guys talk about?

Wife: just silly girl stuff

me: Like Greg?

Wife: ahh yeah, he came up. Why that tone?

me: I heard everything. So, he saw you naked?

Wife: Honey, it wasn't like that. He hooked up with Sarah. It was just playful stuff

me: I know, and you blew Adam

Wife: your being an asshole. We were separated and I don't have to justify myself

me: Did Greg touch your tits?

Wife: stop, its not like that

me: Did you see his cock?

Wife: I did

Her voice and demeanor changed.

Me: Wow, seeing 2 cocks in 1 night. Was it big. Do you want fuck him too

Wife: You are really going to treat me like this?

me: He saw your pussy too?

Wife: I'm done with this conversation

Me: Did you suck his cock or just Adams?

Wife: Fuck you, I'm done

me: Why, so you can go fuck Adam and Greg

Wife: Yup, that's exactly what I'm going to do because I'm such a slut. I'm just a whore that wants to fuck every big cock. I'm leaving

She started crying, left and Sarah picked her up. After cooling off a bit, I texted and apologized. She wrote back: "You hurt me. You made me feel like a slut - and I am not. We were separated. I wouldn't have told you about any of this if I knew you were this insecure. I don't regret anything other than answering all your questions. You should try to meet someone or do whatever you have to do because Im done."

My stomach dropped. I knew this time I had went to far. I had shamed her for something she did when we separated. I already missed her and I knew that I had pushed her away. I don't know why hearing that Greg saw her naked and was attracted to her set me off so much. The Adam thing had spiced up our sex life. It even prompted her to go on birth control let me go bareback. It was a fun month of "get back together sex" and Adam was partly to credit for that.

Weirdly, my mind started thinking about this and whether she would fuck other guys. Had I just pushed her into another guys bed?

---Wife's Perspective

My apologies for not intrucing myself in part 2. My name is Keri, and ironically, I've been told that I look like a young Keri Russell. I have a darker complexion due to some Portuguese and probably bigger breasts than the more famous Keri. Mark and I started dating in highschool and were voted "Best Couple." He truly is a great guy. He is attractive, supportive and has a great sense of humor. He charmed me in highschool after a long pursuit. I had dated one of his friends, but we always had that chemistry. Our sex life was great. At 19, we were probably having sex 4/5 times a week. We did it in risky places and both loved the idea of potentially being caught. He always enjoyed the idea of other guys seeing me nude or in various states of undress. He also never wanted me to wear a bra and encouraged me to wear dresses/skirts without panties. He always told me he was proud to have to a hot girlfriend - and that I should be proud and have fun with it.

I'll get back to the story, but wanted to give you some more background on me and Mark. The things that happened when we were 19/20 didn't happen because I wanted to hurt or cheat on him. We were both young, immature, and figuring things out as we went. I also had relatively limited sexual experience outside of Mark and was using this time to satisfy some of my young curiosity. Most of my friends were hooking up with a lot of guys and living life. I preferred relationshis which kept my number of partners limited.

The night Mark overheard Sarah and I talking was hard for both of us. Mark knew that I had blown Adam the night at the pool and had gone even further 4 days later. Learning that another guy, Greg, had seen me naked and touched his cock against me put Mark over the edge. I understood his anger, but his reaction was hurtful - he meant to hurt and degrade me. I had shared details about Adam because of his curiosity. We were separated at the time and don't regret hanging out with Adam and Greg, or even hooking up with Adam. I was an attractive, single 19 year old girl who had only slept with 2 guys before my incidents with Adam. I regretted telling Mark the level of detail, but he always wanted to know more. It also sparked something new and fun in our sex life.

It hit a nerve that night Mark questioned if I "fucked" or "blew" Greg. We had always trusted and respected each other. That night he was indicating I was a slut and he didn't trust me. The breakup was needed. I also let him know that I didn't care if he hooked up with another girl to make it clear we were done and free to do whatever we wanted.

I was deflated and a little depressed after we broke up. I committed myself to the gym, school work, and running as healthy ways to spending my time. I wasn't looking for a new guy or relationship. I also spent more nights with the girls having wine nights, or watching our favorite shows.

Mark knew I wanted space and respected that. We would occasionally send each other texts just to check in, but no real dialogue, just saying hello. I was about 2 weeks into single life when I got a text from Greg: "Hey, how are you?" I responded: "Adjusting to single life, but good." He wrote back: "I heard, sorry to hear it. You doing okay." We texted for a couple days before he asked if he could buy me lunch or coffee. I agreed to meet him for lunch the following day. Due to time issues, we didn't end up meeting until 4:30 at an outdoor restaurant. I was looking forward to having a conversation with a male. I hadn't talked to any guys in 2 weeks - and although my girlfriends are great, it's different talking to a male. They have a dryer sense of humor and different perspective on things.

We started out with lighthearted talk until Sarah's name came up. I made a joke about him and Sarah and that prompted a more personal conversation. He wanted to know about Mark and what happened. He was engaged and supportive. He hadn't been in a long-term relationship in 5 years. He had tried it, but just enjoyed having fun and living life without any restrictions. He admitted it was probably a personal flaw, but he didn't want to settle down at this time. He knew he would find that person one day, but didn't want to look back and have regrets. I joked that he just wanted to hook up with a lot of girls. He laughed and admitted that was part of it. He also said he respects women and doesn't look at it that one sided. He said saying hooking up is just 2 adults consenting to having a fun time. He said that he's never hooked up a girl and ended things on bad terms.

We agreed to grab ice cream after because neither of us were ready to go home. At some point, the subject of Adam got brought up. Greg said Adam is his friend but he was "bullshit" on how Adam handled things with me. I said it was partly my fault, and it was I risk I took. Greg said "absolutely not" and that Adam should have been respectful and grateful to have gotten together with someone like me. Greg said he would have never treated me like that.

We had a lot of fun and good conversation and ended up parting ways around 9:00. When I got home, I was feeling a giddy about how the night went and how supportive Greg was. Even though we had seen each other naked and touched body parts, the subject never came up. He never made a move on me or invited me back to his place. He was even more mature than I remembered. He acted liked a gentleman and it was nice to talk with someone mature. I also thought about how he openly likes being single and free. He admits that he wants no strings attached.

We texted the following days. On Sunday he invited me for a hike. He piked me up around 10 and we had a great time. On the way home, we grabbed a sandwich ate it in the car. When he arrived at my house, he put the car in park and came around to open my door. I was sure he was going to kiss me, but instead he just walked me to my door, thanked me and asked if we could do it again.

When I went inside, I was puzzled. I thought: "here is a guy that we have seen each other naked; he played with my tits; he seems to be interested; he told Sarah he is attracted to me," yet he hasn't made the slightest move.

The following day he invited me to a late dinner after work. He said he'd get me a 7:00 and dress casual, nothing fancy. I went with my go-to, a cute little summer. It was one with an open back that you can't wear a bra with. My mind was racing whether this was another "friend date" or if he would try something. At this point, I was curious why this extremely attractive, mature, successful guy hadn't tried anything.

Greg picked me up at my house and we went to a nice restaurant. He was still his work clothes and looked handsome. During dinner, we had a great conversation with plenty of laughs. I learned a lot about him. He came from a big family with 3 sisters, a brother and a step brother. He was a self made guy who started his own company after going to University of North Carolina for engineering. His parents divorced after falling out of love when he was in highschool. He worked in NYC before moving back and staring his own firm. He currntly has 6 people working for him.

We wrapped up around 9 and started heading home. On the way home, I told him I wasn't ready to go home. He asked if I wanted to join him and have a fire by his pool I told him that sounds perfect.

When we got back to his place, he grabbed a couple throw blankets, and started a fire and got a glass of wine for us. As we relaxed by the fire, I looked at him and asked if he was attracted to me. He said more than you can imagine. I asked him why he hadn't made a move. He explained that he was worried he made the wrong impression the first night we met. He also hated how Adam treated me. He also said he respected me and Mark and didn't want me to rush anything. He told me he didn't want me to have any regrets or cause any problems with me and Mark. He explained how he grew up with sisters and his biggest lesson was not to make women have regrets. He said he may have commitment issues, but he's taken pride not having hookups where girls feel any regret the next day. It was sweet and I told him Sarah still speaks highly if you. He chuckled and said: "I guess that's a good thing."

As we enjoyed the fire, the wine and good conversation, I looked at the pool and had an urge to go swimming. He went inside to change and grab a couple towels. When he came. outside, he apologized and asked if I needed a swimsuit. I stood up and took off my sundress standing in front of him in my just my panties and asked if this is okay.

He said of course, you look beautiful. I ran and jumped in waiting for him. I was expecting him to take off his shorts like our first night, but he just grabbed our drinks and came in. There I was, topless and flirting with him, but he just kept talking like we were friends.

When we got out, he grabbed me a towel and a bottle of water. He offered to drive me home, but also said he had a guest room since it was late and we'd had a couple drinks. I agreed to the guest room not wanting to go home. After I showered, he brought me a tee shirt and pair of boxer shorts. After I got dressed, he kissed me on the cheek, shut the door and left.

Once he left, I laid in bed confused. I thought about the last few days with Greg and how many opportunities I had given him to make a move. I started thinking about him and felt my hand going down my stomach to my pussy. I put one finger in myself and felt my wetness. I needed some relief, but then realized there was a better option.

I stood up, took off Greg's tee shirt and boxer shorts and went to his room completely naked. He was laying on his back in his boxer shorts when I walked in. I said: "Greg, I couldn't sleep."

He stood up, grabbed me by the ass and kissed me. He said: "you don't know how bad I want this. Are you sure?"

I fell onto his bed and spread my legs for him and gave him a sexy look. He looked me up and down, soaking in that I was completely naked waiting for him on his bed. This was his opportunity to explore my body fully with no restrictions like the first night. He leaned over and started sucking my tits. His hand went from the other tit, down my stomach to my exposed pussy. He kissed his way down to my stomach and started licking my pussy. I remember his complimenting my pussy as he explored it with his fingers and tongue. He was being delicate and taking his time to explore my 19 year old pussy that was available to him. I watched he fingered, explored and licked my pussy. I looked at his body and could see his cock straining against his boxers. I grabbed his head and brought back to mouth to kiss him. After our tongues explored each other for little bit, I paused and asked him: "Greg, do you have a condom?"

He stood up, took off his boxers, and went to his bed stand to get a condom. His cock was huge, probably 8 inches and thick. It wasn't the "coke can" as Sarah called it, but it did look like the smaller cans that sodas come in. He pulled out a box of Magnum condoms, which was the first time I had seen one. I watched him roll it on his hard cock and began worried whether my pussy could take it all. As he got into bed, I asked him: "Greg, can you go slow."

He kissed me and rubbed his big dick against my wet pussy to lubricate the condom. As he put his tip in me and I couldn't believe how much pressure I felt. My pussy was wet, but it felt small trying to stretch to accommodate his girth. I reached down and spread my pussy to help him insert more. After a few minutes, we found our rhythm. He asked if I was okay and if he could go deeper. He spent several minutes slowly working his dick in and out of me to allow me to adjust to his size. When he finally was able to bury himself in me, I looked down and watched my stretched pussy and his glistening cock going in and out of my pussy. I whispered in his ear that I was cumming.

At some point I got the courage to ride him. It felt like his cock was in my stomach reaching parts that had never been touched. As I rode his cock, I thought about how much I wanted to impress him. I kissed him and told him how much I loved his cock. He started grunted and cumming. For a moment I wished the condom wasn't on him and I could feel his seed fill me. I rolled off of him exhausted and watched him take off the condom that covered in my cum.

I feel asleep in his bed. I woke up around 6:30 with him laying next to me. I looked over and thought about last night. Unlike Adam, I had no regret or second thoughts. Adam had capitalized on an opportunity get in my pants. Greg had made me pursue him. I was the one who walked into his room naked and looking for him to fuck me. He had made me come to him.

I slowly pulled the sheets down and kissed down his stomach. As his cock hardened, I watched him open his eyes. I told him that I wanted to thank him for last night as I took him into my mouth. Unlike Adam, he told me when he was about to cum, but I kept sucking him until he came in my mouth. I wanted him to watch me swallow.

After we showered, he made me breakfast and coffee before dropping me off.

Stay tuned for Part 4. Greg gets me to expand my sexual horizons.