An Inside Man for my Girlfriend!

By: Anna's Cuck

Hello,

I wanted to write in to describe my experience of becoming a cuckold over the past year. My girlfriend's name is Anna. We're in our late twenties and have been dating for a couple years now.

Our sex life could best be described as awkward and intermittent. We're both naturally submissive so neither of us is adept at taking charge and leading the action. Despite an initial flurry of sexual activity after we first started dating, we fell into a routine quite quickly that involved having vanilla sex just once or twice a month. She only gave the brief blowjobs that ended well before I ever came. And she always made me wear a condom. After dating for two years, I had never cum onto her body or into her mouth or pussy.

Anna wasn't prudish though. She was actually very open and accepting of different sexual proclivities. Her parents were hippies from the 70s who lived a 'sexually free' lifestyle. She watched porn and masturbated regularly (even occasionally with me in the room with her). She didn't dress in a stereotypically slutty manner but she was very comfortable wearing thin and loose fitting clothes without underwear. She almost never wore a bra and all my friends had seen and commented on her nipples poking through her shirt on multiple occasions.

Unfortunately, my work interrupted our relationship. I had to travel to a different country to support a new project and I had to be there for a full uninterrupted year due to my visa status. Anna was depressed by the situation but committed to stay together with me. We talked about it a lot over several weeks and eventually agreed to maintain an 'open' relationship while we were apart. We both heard stories from friends who had long distance relationships that frayed over time due to suspicion and jealously and concluded that an open relationship with regular and honest communication was the best path for us. The basic agreement was that we were both free to pursue temporary relationships with others while we were apart but we had to talk to each other every day and we couldn't have any secrets.

One night while out at a bar with some work colleague, I confided to them about my situation with Anna. They told me to stay strong and not to worry at all. They said it was a temporary inconvenience at worst and it was for the best for our project. As we left the bar though, one of my colleagues named Jeremy stopped me in the parking lot. I wasn't very close with Jeremy so his interest in talking more to me was a bit strange.

After our other colleagues had driven off, Jeremy walked me to my car while consoling me about my unfortunate situation with Anna. Once we got to my car, I tried to say goodbye but he stopped me and asked if he could give me some 'real talk'. I just nodded not knowing what to do. He then started to explain that Anna would probably stay chaste for a couple months but eventually she would meet another guy and go off with him. And by the time I got back, she will have been dating the other guy for almost a year. She would have deep feelings for him and it was '50/50' at best if she'd call that off to get back with me.

To be honest, Jeremy was explaining some of my worst fears. I tried to play it cool though and ask him why he was telling me all this. Jeremy then put his arm around me and said that I needed an inside man to look after Anna while I was gone. I was still a bit perplexed and asked what he meant. With a bit of a grin, he said that I needed a guy to keep her 'warm' while I was gone to keep the other guys away who might want to steal her from me. Catching on, I asked if he meant that he would keep Anna warm and he nodded enthusiastically. I was ready to tell him to fuck off but he kept talking. He explained that he would make sure that Anna didn't see any other guys and promised that he'd end the relationship a full month before I came back. I asked how I could trust him and he said that he couldn't possibly go back on our agreement since we work together in the same office.

I was simultaneously pissed off at Jeremy for even suggesting his idea and starting to think that his idea might actually be in my own self interest. I challenged Jeremy how he'd be so sure that he could seduce Anna. With complete confidence, he said it wouldn't be a problem at all. For sure, Jeremy was tall and attractive. He wasn't the type of guy Anna had even been with before though. He said he was an expert and there wouldn't be any doubt if I committed to helping him. I asked how I could help him hook up with my own girlfriend. He explained that if I was supportive of her and provided him some tips along the way, it would be a sure thing. I was skeptical but also a bit intrigued. I wondered if my long term chances with Anna were better off with Jeremy or up to chance. I didn't commit to anything but just told Jeremy I'd think about it before driving away.

A few days before I left, I was talking to Anna in bed. It was a bit of a meandering conversation about our relationship but I eventually said that I wanted her to really have no insecurities about starting new relationships. She agreed that she wouldn't. I then somewhat meekly asked that she just didn't hook up with someone who is just like me. Anna laughed and promised that whoever she considered would be the polar opposite of me. She jokingly said she would only shop the isles of the market that she typically doesn't walk down. Then more seriously, she asked why I was concerned. I explained that it would feel a bit like she was replacing me if she dated some guy who was just like me. But if he was very different from me, then it would be more like a temporary escapade. Anna kissed me and promised to not date anyone who was remotely similar to me.

A day later, Jeremy caught me at work and asked me how I was feeling about his proposal. I was conflicted but eventually admitted that I was willing to give him a chance. But I cautioned that if Anna wasn't into him, then I wouldn't force it. And if he was successful, he had to promise to give me regular updates on how it was going with her. Jeremy was ecstatic and told me to have any worries. He said he'd let me get comfortable in my new spot for a month or so before contacting me and working out a plan.

Skipping ahead, I moved for the project and got settled in my new location. Don't want to get into too many details because it might be obvious where I moved but it's safe to say that I was in a relatively remote location and I definitely had a lot of time to myself. Anna and I talked every day which helped. She was very supportive and encouraged me to stay positive. The idea of both of us being in an open relationship felt more and more ridiculous by the day though. Even if I wanted to find another girl and was capable of seducing her, there weren't very many to come by.

I had almost forgot about my deal with Jeremy by the time he texted me. Surprisingly, he said that he had already run into Anna already at the coffee shop. He said it was just random chance but I suspected that he had staked it out knowing that she went there almost daily. He said Anna was waiting for her coffee and he just walked straight up to her and introduced himself. And after they both got their orders, he asked Anna to sit with him and she did. I didn't entirely believe him but he described Anna as flirtatious and definitely open to his advances. I asked if she mentioned me or our relationship situation at all but Jeremy confirmed that she didn't. Jeremy also didn't mention that he knew me at all. Once they finished their drinks, Jeremy asked Anna for her phone number and she gave it to him. He even sent me a screenshot of her number in his phone as proof. I asked what his plan was but he didn't give too many details. He said he wasn't gonna rush it and encouraged me to talk to Anna to get her side of the story.

Later that day, I reached out to Anna and asked her how her day was going. After talking about her work for nearly twenty minutes, she finally mentioned that a guy (Jeremy) had approached her in the coffee shop and she gave him her number. She said she was actually very embarrassed that she did it. I told her that it was ok and she shouldn't feel bad. She admitted that since I had left, she had been trying to be nicer to random men who approach her. Obviously she had been approached many times before while we were going out. But she was trying to respond more positively to their attention now and reciprocate their interest. She said that she had chatted randomly with a few different guys over the past weeks but Jeremy was the first guy she agreed to give her number.

I asked Anna what she thought about Jeremy. She initially said she didn't know. She mentioned that he was "attractive" though not really her normal type. But she said that she was trying to be more open and broaden her horizons. After a brief pause, she remarked that he was very confident and that stood out to her. He wasn't timid talking to her like other guys sometimes typically are. Then Anna said "speak of the devil" and explained that Jeremy had actually just texted her. She summarized his message that said it was nice to meet her at the coffee shop and said they should meet up for drinks on Friday. He didn't ask if she wanted to meet for drinks or if she was available... he just said let's meet on Friday at 8pm. Anna was bit flustered and asked me how she should respond. I said she should give him a chance, meet him for drinks, and see where it goes. I added that I supported and loved her no matter what happens. Anna replied with a heart and then said her 'date" with Jeremy was confirmed.

The next day, Anna texted me and said she was nervous for her date. She explained that she hadn't been on a first date in a long time. Before I could respond, I also got a text from Jeremy asking how my conversation went with Anna the day before. I meekly congratulated on his date but relayed that Anna was a bit nervous. Jeremy told me that I needed to support her and give her confidence that the date would be successful. I asked what he meant by successful and Jeremy just replied by saying that we both have the same goal at the end of the day.

I then replied to Anna and told her that I was sure her date would go great and she should just have fun. I even added that she could take my credit card and buy a new dress for her date if she wanted to. Anna seemed pleased by response but asked if I really wanted to pay for new date outfit. I confirmed I did but asked for her to at least send a photo of what she chose. Anna agreed and said she'd go to the mall to find something.

On Friday afternoon, Anna sent me the photo of the dress she had bought for her date. It was a red dress that clung tightly to her body and had a short skirt. She looked incredible in it but I had never seen her in something like that before. As always though, you could easily see her nipples poking out and you could tell that she wasn't wearing a bra. I texted back that she looked great and wished her good luck on her date. Anna responded by saying she had butterflies in her stomach but she hoped it would go well. She promised to text the next day and tell me how it went.

A few hours later, I could hardly sleep and started masturbating just imaging all that Anna and Jeremy could be doing together. Just before I was about to cum, Jeremy texted me. He had just returned home from the date. He said it went great. I asked for more details and he gave me the brief rundown. They met at the bar. Anna wore the tight red dress that she had sent me the picture of and Jeremy mentioned the visibility of her nipples of course. After a brief hug, they sat together near the end of the bar. They had several drinks while chatting. He said Anna smiled and laughed a lot and was definitely accepting his flirtatious advances. He said he put his hand at various points during the night on her back and on her leg which she accepted without hesitation. After they finished their last drinks, they walked together down the street towards her car. Then at her car, Jeremy said they made out for several minutes and Anna let him grope her whole body. I was crushed and turned on simultaneously. Gloating a bit, Jeremy said he was certain that he would fucking Anna in no time. I didn't know how to respond. I thanked him for telling me everything and said I'd talk to Anna tomorrow to get her side. Jeremy reminded me to keep encouraging her and he promised to keep me in the loop for whatever happens next.

Shamefully, I continued masturbating and came almost immediately after ending my conversation with Jeremy. I fell asleep very late and work up the next morning to a message from Anna. I asked her how her date was and she said it was good at first without providing very many details. Eventually though, she broke down a bit and said she felt bad to tell me what actually happened. I reassured her it was ok and that I didn't have any misconceptions about what dates would potentially lead to. Anna then admitted that she did kiss Jeremy though didn't provide any of the extra details he had descried to me. I told her that I was happy she potentially found someone she likes and encouraged her to keep dating him. Anna lamented that she had been feeling quite horny since I left.

She obviously hadn't have any physical interaction with me and she also hadn't really been masturbating since I left. I told her that her feelings were completely normal and I still loved her. She explained that she did masturbate though after her date with Jeremy. She had been so horny all night, and then they kissed, and then she masturbated while she was still in her car in the parking lot. I asked her if she wanted to have sex with Jeremy and she admitted that she did. She said that she felt bad to tell me that but she didn't want to lie to me. I thanked her for not lying and again reassured her that I was aware of the likely outcomes of her dating other guys. I said she shouldn't be thinking about my feelings when she is out on dates and she should take this opportunity to chase her desires. Anna seemed surprised and relieved by my response. I asked her when she would meet Jeremy again and she replied that they were planning to meet again the next night. I told her good luck and we agreed to talk to each other again in a couple days.

Following my conversation with Anna, I chatted with Jeremy again. I told him that Anna really likes him and wants to go further with him. He said he knew but was glad I had heard it from her as well. I asked him what he was planning for their next date and he said Anna was gonna come over to his apartment and they were gonna hang out in the hot tub together.

After 36hrs of agony, I got a message first from Anna. She said her date was good and explained a bit more of what happened this time. She said they had a couple drinks in his apartment before going together to the hot tub at his apartment complex. She was wearing her black two piece bathing suit under her clothes and just stripped off her shirt and shorts in front of him at the hot tub. They got in together and enjoyed the water for a bit next to each other. Anna admitted that she kissed him first but added that they were both quite handsy under the water. Then they went back to his apartment and took a shower together to clean the chlorine off. She explained that they eventually both got naked in the shower and continued kissing and touching each other.

And she sucked his dick while touching herself and they both came in the shower. I had hundreds of questions but the first thing I asked was where he came. After a pause, Anna admitted that he came in her mouth. She explained that she had never swallowed cum before and she thought previously that it was gross. But in that moment, she was also cumming at the same time so she swallowed it quickly and actually kinda enjoyed it. I felt terrible that Jeremy had already done something with Anna that I had never done before. Anna apologized but I told her that she didn't need to. To be honest I wanted to ask about his dick size but didn't know how to ask without completely humiliating myself. Anna then explained that after the shower they watched some shows together while cuddling on his couch before she went home. I thanked Anna for telling me everything and said it seemed like her new relationship was very exciting.

I knew Jeremy wouldn't wait too long to message me as well and he didn't. While Anna gave a meandering review of the whole night, Jeremy jumped right into the details. He said that he actually fingered Anna a bit in the hot tub and also pinched her nipples which she seemed to really enjoy. And then back in his shower, he saw her fully naked and touched every part of her body before she got down on her knees and sucked his cock. When he pulled his trunks down, he said Anna was astounded by the size of his cock and almost immediately took it into her mouth. He said she wasn't the most skilled "cocksucker" but she definitely put in a lot of effort including sucking on both of his balls. He said that he told her that he was going to cum and she verbally begged him to cum in her mouth. He confirmed that she came from rubbing her clit at the instant that he started to cum in her mouth. She then swallowed his entire load and continued to suck him dry for another half minute until he pulled her up.

I didn't know how to respond to Jeremy at all and he noticed. He told me not to worry about anything that that he'd take good care of Anna until he came back. I asked how big his dick was and he said it was "8" and pretty thick too". He asked me if I ever did the toilet paper roll test but I said that I didn't even know what that was. He explained that if your dick fit in a toilet paper, then it was definitely on the small side. He then sent me a pic of his dick next to a toilet paper roll and it looked huge. His dick was at least twice as long and the roll was half as wide as his dick. Later, I tried on myself and found that my dick fit easily inside the toilet roll and barely stuck out of the far end. I already "knew" that Jeremy's dick was bigger than mine but it hurt to be able to quantify exactly how much.

For the next few days, Anna and Jeremy texted each other but didn't meet in person. Anna told me that Jeremy asked her to send him a picture of herself. She said she sent a photo of herself in robe in the bathroom. She sent me copy and it was quite sexy. The next day though, Jeremy shared the photo she the photo she actually sent him. It was still of her in a robe but it was a different photo with the robe more separated showing more cleavage and leg. I later messaged that Anna that Jeremy had already seen her naked and joked that she didn't need to tease him with robe pics. Anna replied with haha but later Jeremy said that she sent him more pics. She was in panties for one and completely naked for the other. He didn't share those pics though. Anna had never sent me a fully nude photo before so it was another thing she had done for Jeremy that she had never done for me.

They arranged their date for the next weekend on Saturday night. Again, Anna went to the mall a bought a new outfit for herself with my credit card. This time she got a pink dress which was a very atypical color for her. This dress seemed a bit looser than what she wore for her first date but still very short. I instantly imagined how easy it would be for Jeremy to reach up her skirt and finger her while she was wearing it. She also bought a new thong at Victoria Secret that was pink but semi-see through. She sent me a photo of the outfit just placed out on the bed so I never actually got to see her wearing it. I asked Anna if she was as nervous this time as last time. She said she wasn't yet but expected to be once she started getting ready to go.

Anna also told me that they planned to meet at a bar that was in close walking distance to our apartment. I asked immediately if she that she would bring Jeremy to our apartment and she just said it was an option. Talking to Jeremy a bit later, he said that going back to the apartment was definitely planned. Independently, I wished both of them luck and they each agreed to check in with me again on Sunday to tell me how it went.

Around Sunday afternoon, Anna was the first one to message me. It had been an agonizing wait all morning waiting for some confirmation of what happened. She apologized and said she was tired from staying up so late. I told her it was ok and asked how it went. Anna said the date was pretty normal at the bar. They just had drinks and chatted a bit. Then they decided to head back to our apartment. She noted that they stopped a kissed a few times before getting inside. Anna then paused and asked if I really wanted to hear the rest. I told her I did. She then admitted that they had sex and that Jeremy had stayed over for the whole night. I was devastated mentally but had a rock hard erection at the same time. I tried to ask about some of the details without prying too hard. Eventually admitted that they both got naked (obviously), she sucked his dick for a few minutes, and then they got on the bed together. I asked if they used a condom and Anna said no. I asked why.

Past the point of softening any blows, Anna explained that the condoms we had for me in our bedside table didn't fit Jeremy. This was probably the peak of my humiliation so far. Of course all three of us were well aware by this point that Jeremy's dick was much bigger than mine. The condom not fitting on Jeremy and the resultant bare sex they had just reinforced the truth like a wrecking ball. I stumbled a bit trying to ask what happened at the end and Anna just bluntly responded that he came inside her (yet another act that Jeremy did almost immediately with Anna that I had never done before). After tolerating my questioning for long enough, Anna said she was still tired and was gonna try to nap. I thanked her for telling me everything and said we'd catch up again during the week.

I masturbated and edged myself no less than five times before Jeremy messaged me. He asked if I had talked to Anna already. I said yes and congratulated him on his success. Jeremy laughed and said it was never in doubt. He asked what Anna told me and I gave him the brief rundown. As I told him Anna's story, he broke in a few times to add details that Anna glossed over. He said that they were in a corner booth in the bar and Anna had grabbed his dick through his pants under the table. And walking back to the apartment, she told him she was wet and asked him to fuck her all night.

After they got into the apartment and into the bedroom, Jeremy confirmed that he didn't wear a condom. He didn't mention even trying one on. I wanted to ask more but didn't. Jeremy went on to describe the various positions that they fucked in for nearly half an hour and the large quantity of orgasms that Anna had throughout. And he said they were in missionary position and kissing each other and the moment he erupted inside of her. I told him that I thought he was the first guy to ever actually cum inside Anna and he just laughed again. After he pulled out, Anna went to the bathroom and cleaned off. She then came back and they slept together all night completely naked. I congratulated Jeremy once again and he thanked me for the help along the way. I asked him what he planned to do next and he just said that he was gonna continue fucking Anna as much as possible until l came back.

It's been another couple months since their first dates and Anna and Jeremy continue to see each other three or four times a week. I can't recount every story but Jeremy has continued to add to the list of things he has done with Anna that she has never done with me. In addition to cumming in her mouth and pussy and getting nude photos from her, he has also given her facials, fingered her ass, filmed her having sex with him, received a blowjob from her while he was driving, and had sex with her semi-discreetly in public. I still talk to Anna regularly but she provides less intimate details of what she does with Jeremy.

One of our friends saw Anna and Jeremy together on a date once and reached out to me insinuating that she caught Anna cheating. I couldn't explain the actual truth to her so I just said that Anna and I had actually broken up when I left but we were both trying to not tell too many people about it because it was still a bit raw emotionally. Our friend immediately apologized and said she'd keep our secret safe. She remarked even that she knew Anna would never actually cheat on me and that's why it was so surprising to see her with another guy.

I still have another eight months before I return home and I'm not sure what will happen between Anna, Jeremy, and I when I do.

Anna's Cuck - mahmiss@tutanota.com

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