Jen's Follow-Up Meeting with Drew

This is a story about an encounter with a guy named Drew that Jen and I had. This story takes place about a month after Jen got her first and only sensual/erotic massage. But this story begins a few weeks prior to Jen receiving her massage.

When Jen decided that she wanted to get a sensual massage, she said that because this was not the normal type of massage that she usually gets, she wanted to know who the person was that would be giving her the massage before she got it. She wanted to make sure that she was attracted to them, that she liked their personality, and most importantly, that they could give a good massage and that they knew what they were doing and had done it before. Those were her criteria.

In order to make sure that we got someone who Jen approved of, I went online and met a bunch of different people and chatted with them. I narrowed it down to a few different candidates, and Jen decided that we should meet with each of those people in person before getting a massage. The person who we liked the most based on conversations was a guy named Drew. Based on his photos, he seemed to be a handsome guy that Jen liked, and when he was texting with me, he seemed to have a good personality. So, we decided to arrange a meeting with him, and we picked a weeknight and got a babysitter for the kids and we went out. We met him at a local bar/restaurant about a five-minute walk from our home.

We met up at the bar pretty late. The bar closed at 11 o'clock, and we met around 9:45. We got there first, and then Drew came in. We were sitting in a booth that had two seats on one side and a bench on the other side. Jen and I were sitting side by side in the two seats, and Drew came in and was sitting across from us on the bench. We started a friendly conversation -- there was no awkwardness at all, and I could tell right away that Jen was immediately attracted to his look. He looks very similar to Frank Grillo, who is a popular actor on TV shows and movies. He had very thick black hair and neatly trimmed facial hair, and he was the type of look that Jen found attractive.

Drew was very pleasant to talk to and converse with. He was telling us about how he was brought up and where he was from. We engaged in enjoyable conversation that wasn't sexually involved or detailed. It was just a good conversation as if we were having friends for a long time. That conversation led to Drew saying how happy he was to have met us and that he could tell based on his interactions with me alone that we could be friends.

He was forthcoming and outgoing, but he did admit that he doesn't really know how to give massages. He's not a professional, and he's not even an amateur masseur. He's given a couple of massages to girlfriends, but he said that he wanted to see if he could be in contention, so that's why he said he gave massages. He figured that if he were chosen to give the massage, he would go on YouTube and do research and figure out the best way to give a massage. We appreciated his honesty, and we laughed at that, because we were all getting along well.

Around 10:30 or so, maybe about 45 minutes after our conversation began, Jen had to go to the bathroom. She left for a couple of minutes, and Drew asked me how I thought it was going.

I told him it was going very well, that the conversation was good, and that I could tell Jen was into him. He was happy to hear that.

Jen came back from the bathroom and said to me, "You know, I've been sitting on your side the whole night. Do you mind if I sit next to Drew?"

And I said, "No, go for it." So, she sat next to Drew, and we continued the conversation.

After a few minutes sitting next to Jen, Drew said, "You're so close to me, and you smell so good. Do you mind if I kiss you?"

And Jen said, "No, I don't mind at all."

Drew pulled Jen closer to him and they started making out and kissing. We were in a booth, and it was pretty close to closing time, so there was no one looking at us, but they were really going at it and kissing a lot, and there was a lot of PDA.

In the middle of it, Drew took Jen's hand and put it on his crotch and said, "Look what you're doing to me." Jen told me after that Drew was very hard, and she could definitely feel him, and he felt pretty big and hard.

After their makeout session we chatted for another few minutes and then decided to leave. The place was closing, and we said goodbye to Drew, and said that we'd all keep in touch, and before he left, we made a chat group on an app called Telegram that we would communicate on, and we said goodbye. He left, and we went back to our place.

Jen told me that she really enjoyed meeting with him and that she thought he was a nice and a good-looking guy. But she said that she definitely did not see him as the type of guy who would be giving her a massage, so we should still look for that person. She told me though that she did see him as a potential sexual partner in an MFM type situation, and that she would be into being with him in an MFM, which was really cool because she was pretty forthright and outright about that, and she usually is pretty discriminating when it comes to choosing a sexual partner. It was nice for me to see that she was actually thinking of him in that context.

We continued our conversation on text with Drew, and he sent Jen a couple of unsolicited dick pics a couple of times, which to me is a little bit of a turn-off. But he said to her, "I just wanted to show you how hard you made me and how I think about you, and I jerk off to you often, and I can't wait to actually see you again."

And while she thought that dick pics were a little bit gross, she was really happy that he was interested in her and was pursuing her. Because, with Jen, more than anything, she wants to feel wanted, and she was definitely feeling wanted by Drew.

Fast forward - Jen had her massage about two weeks after our meeting with Drew, and we were still in contact and still texting each other.

Jen said, "You know what, we should all meet up again for some possible fun."

We started trying to work out a date with Drew, but the scheduling and the schedule was difficult for him and for us. He was traveling a lot for work, and we had our kids that we had to figure out arrangements for, but ultimately, we figured out a date that would work for both of us. It was a Friday night, and we made plans for our kids to sleep at their friends' houses. We set up a date for Friday night, which would start with dinner and drinks at another local restaurant, and then we said that if things went well, which we assumed they would, we would go back to our place for the rest of the night. This was the first time that we would actually have someone that we didn't know well come over to our place to do this sort of thing. The only other time was when we had a mutual friend sleeping over, and he ended up having sex with Jen in our place after I had left for the day. But we made a plan with Drew and felt comfortable about the arrangement.

A few days before the Friday date that we had set, I got notice that I needed to partake in a client dinner. The client's dinner was about two hours away from our home. I wouldn't be able to get away with not going, and it was on the Friday that we were all supposed to get together. So, I discussed it with Jen, and we came to the conclusion that because she had a comfort level with Drew, even though she only met him once in person, she felt that it would be okay if she does dinner and drinks without me and then I can meet them back at our home when they get there.

And worst case, which isn't really worst case, I would come a little bit after they got to the house so that they would be able to sort of get a head start. The thought process with getting a head start was that although Jen did like the MFM aspect and she did like to see me watch her getting fucked, she had some issues with the overall concept of the MFM. Those issues were that she always felt that she had to be concerned in her mind about making sure that both guys were receiving enough attention and getting pleasured enough. She said that it gets in her head and sometimes takes away from the moment. She also said that she often felt inhibited when she was with another guy and me because she felt weird about moaning or expressing herself or really getting into it with another guy because of the fact that I was there watching her. I always told her that she is in her own head, but we can't control our feelings and emotions.

It is weird because she enjoyed me being there to an extent, but she also enjoyed just having fun on her own without there being another observer there. And even when she knows that I am recording it with audio or video, she still tells me that it makes her feel a little bit inhibited. So, I told her that I wasn't going to record anything, but if she got started before, and if she felt like she was in the mood, she should feel free to record it. Jen told me that she would try to record parts of anything that happens.

Friday finally came around and everything was going well. I had already left for my client dinner and Jen was getting ready to go out. She picked an outfit that wasn't a super sexy outfit, but it also wasn't casual. She could get away with wearing that like a school function as well as just wearing it to go out at night. They were supposed to initially meet a little bit earlier but they both got delayed so they ended up meeting around 8:00 PM at restaurant next to our home.

Jen was very about staying in communication with me. She texted me a pic of what she was wearing, she texted me when she got to the restaurant, she texted me when he got there, and then an hour after that she texted me that they were heading back to our place. Jen told Drew that I was coming back to our place as well, but that I would be a little bit late. And then when she got to our place, she texted me that they made out a little bit and Drew was in the bathroom, and they're sort of starting so she's putting her phone away. That was at 10:22 PM. I greatly appreciated the updates, and they made my time away so exciting and really motivated me to get home as quickly as possible.

After about 20 minutes after the last text from Jen, while I was driving home, I got a text message with a video attached. I wanted to get home as soon as possible, but I needed to see this video, so I pulled my car over to see what she sent me.

The whole video was about 10 minutes long.

It started with Jen, who was already topless, putting the phone on the dresser with the camera on and recording it, and then Drew, who was already laying naked in the middle of the bed, with his dick pretty hard, and was waiting for Jen and staring at her body.

Jen approached the bed. She was just wearing her thong, a very sexy black thong, and Drew told her to spin around so he can see her amazing ass. Jen spun around in the thong and Drew made a comment about her beautiful ass and then she crawled onto the bed naked and laid down on top of Drew, with her thong still on. Jen grabbed his dick, and she started stroking it and it got very hard. Drew was about an inch or an inch and a half longer than me and a little bit thicker than me as well. Jen kept stroking his cock with her hand and then she put it in her mouth, and she started giving one of her world-famous blow jobs. Jen gives incredible blow jobs and clearly Drew thought so as well. Jen was alternating between sucking and stroking and as she was doing that, Drew moved her a little bit so that he had access to the rest of her body. He then reached down and moved aside her thong and he put a couple of fingers inside her pussy and started fingering her while she continued to suck on his cock.

Jen really loved that and started moaning while she kept sucking on his cock. Then he had her stop blowing him and he started passionately kissing her. They kissed for a couple minutes while he was still fingering her. Then, he surprised me by telling her to bring the camera to him. So, Jen moved the camera away from the dresser and gave it to Drew, and Drew started recording with one hand while he was fingering Jen with the other hand, and it was incredibly sexy. Drew then pushed Jen's head back down on his crotch and just his dick in her mouth. Jen's head was laying on Drew's crotch, with Drew's cock in her mouth, and stroking it at the same time with her hand, while looking at the camera that Drew was holding. She was really going to town sucking and stroking his cock and he said that felt like he was gonna cum soon.

He was talking dirty to her and said to her "that's my good girl, that's my girl".

Then he asked her "are you gonna be a good little slut?" and Jen answered "uh-huh" with Drew's cock still in her mouth.

Then he said, "am I going to cum in your mouth?" and Jen said "mmm-hmm", and he said, that's right good girl, give me a kiss before I cum in your mouth.

So, Jen stopped sucking and kissed him and then went back to alternating sucking and stroking him vigorously.

He said, "I'm about to cum", and he exploded in her mouth with an incredible amount of cum. It looked like a volcanic eruption of cum and Jen was not prepared for the volume of it. Jen swallowed as much as she could but then started coughing and gagging as a ton of cum leaked out of her mouth. She gasped and said, "Oh my God, that is so much cum! I think I threw up a little bit of your cum." And they both laughed.

Jen went to the bathroom right away to clean up and Drew ended the recording. It was funny to me as well that she was clearly overwhelmed by the amount of come she got because I am not a huge cummer. I probably cum an average amount but I do not have a huge load and Drew had a tremendous load that she was totally unprepared for, so that was an interesting surprise.

After she cleaned up in the bathroom, Jen put on a robe, made a couple of drinks and Drew and her took a break to have a drink and get some air. Jen texted me that she actually would be fine with Drew going home because she was getting a little tired, but Drew told Jen he wanted to stick around and recover for round two, and he told her that it takes him a while to get hard again, so he wanted to wait around. I was on the way home and got back close to midnight, which was an hour after they were hanging out on the porch. By the time I got back, I went into the house and heard them talking and I went into the bedroom and found them both naked. Jen was lying on the bed and Drew was laying on the bed as well with his head resting on Jen's stomach, with one of his hands on her breasts, just massaging and playing with them and they were talking about random things.

I went into the room and said hi. They both seemed happy to see me -- Drew gave me a hug and Jen gave me a kiss. I started to get undressed, and Jen told both of us that she is pretty tired and she didn't think she could go another round, and she suggested that maybe we should pick this up a different time, and Drew said OK, no problem. He was a little surprised because he was hoping that there would be some more action and more activity, but he was a gentleman about it and respected Jen's decision. Drew started getting dressed and I started making out with Jen a little bit while he was getting dressed, but then he came out and he was in clothing, so we both walked him to the door. He gave Jen a very long kiss and she was still naked, so he grabbed her ass and gave her a smack and he gave me a quick hug and he left.

Once Drew left, I was, you know, being very touchy with Jen, and I asked her if she really meant what she said that she was tired and couldn't go another round, and she said, no. She said that she definitely was a little bit tired, and she did not want to go a whole round of an MFM, but she wanted me to fuck her. So, we made out a little and had some really good and intense sex. I came very quickly due to the excitement of the whole situation, but Jen was amazing as always.

After our sex, she told me what transpired after the first video she sent me. She told me that when she was out on the porch with Drew, he had a smoke, and they were having a drink and said that he really wanted to get another blowjob and fuck her, and he asked her a couple of times. She told him that she hadn't come yet and she wanted to get off too. She also told him about her "policy." Although this may sound a little contradictory, Jen doesn't love to have full sex with someone the first time that she meets them. Obviously, she has before, but it's not her ideal situation. She prefers meeting them once or twice in a sexual capacity before she has penetrative sex with them. To me that sounds a little bit weird because of the activities that we participate in when we engage in these shenanigans. And there have been situations that she has had sex with people the first time she's met with them and, one-night stands. But in her mind, if she could script it, her ideal situation would be to have sex the second time she met with someone and not the first. And to her the sex is more of an intimate act than giving a blowjob.

So, for the second round, post-drink/smoke, Jen set up the camera again as well so that I didn't miss anything. She pressed record, took off her robe and she laid down on the bed. Drew followed her and got on the bed, and he started going down on her and eating her pussy out. Jen's pussy is completely bare and looks amazing, and her pussy is always incredibly tasting and smelling, so Drew started eating her out and then started fingering her as well at the same time, which Jen absolutely loves. She loves the combination of being eaten out and fingered at the same time, and she was getting a lot of enjoyment from it. Jen's legs were locked around his head, and Drew was really doing a great job eating her out. After a few minutes, Jen was moaning loudly and came and seemed to been having a very long orgasm because she was coming, and even when she was slowing down she was still having the "aftershocks" of orgasm and she really seemed to love it. After Jen orgasms, she gets very tight and could get tired, and this time, she was basically done. Drew still wanted to fuck her then, but she told him to just cuddle, and that is around the time that I walked in, when they were chatting after Jen's orgasm.

Obviously, we didn't get to do the MFM, and Drew never got to fuck her. Jen told me that although Drew had a tremendous amount of cum, and that was sexy, as Jen LOVES cum, Drew's cum tasted bad and she said that it actually tasted a little bit chunky, and she didn't love that and it made her nauseous. She did like his personality and she thought he looks good, but also said that he was a little bit too forceful with her, and overall, she told me that she did not really want to have sex with him again or have another sexual interaction.

Over the next few weeks Drew he was texting the group, and he was texting her individually as well, and sent her a lot of dick pics. Jen "broke up" with him very nicely, saying that she and I are re-evaluating our relationship and that she is currently taking a break from other people and just focusing on each other, and that is where she left it.

Every now and then Drew will text Jen with some innocuous "checking in" type of text, hoping that she will throw him a bone eventually, but she shrugs him off and isn't very responsive. She's hoping that he just gets the idea that you know this is done and I think he does get the idea, but I think that in his mind hope springs eternal. He also never got the chance to fuck Jen and I think he realizes that Jen has an incredible pussy, and it would be an amazing experience. I don't think that's ever going to happen though - Jen basically told me as much. It was an enjoyable experience, but that chapter is done. Onwards and Upwards!