Monday, 16 December 2013

Mike and Jen’s First Time(s) – Part 1

This may never be published as Mike and Jen still aren’t sure how much of their first time(s) they want documented – they have steadily been accepting the idea of putting more detail online so I expect by the time we finish writing it there will be explicit details of everything (and yes, they are watching me as I write this sentence).

On the Wednesday morning, Mike woke me up by going down on me and once I’d cum, he fucked me until I came again, but he held back from cumming. While he showered I went down on Jen and got her close to cumming, but (with her consent) we stopped before she actually came. Jen and I showered separately and we all got ready for work – just before we left, I pulled her on to the sofa and we had a quick 69 – again not enough for her to cum, but enough to get her nice and wet (and our juices over each other’s faces). We often do things like this just before heading out and while it can mess up our clothes and hair a little, it’s worth it to get the scent of Jen on me.

I didn’t leave her alone on the way in to Uni either and took the opportunity to caress her on the bus. I waited until it was packed and I was pressed right up against her back, then slipped a hand under her skirt and fondled her. For a couple of minutes I just played with her pussy, slipping the tips of a couple of fingers in to her and rubbing her juices around her lips. She felt nice and wet and pushed back against me a few times but at that point I couldn’t tell if she was asking me to do more or to stop teasing her. At the next stop, she pulled away from me when people pushed past and turned to face me when more people crowded on – she whispered to me that her pussy was tingling and couldn’t take much more, so when the bus started to move again, I pushed against her and slipped my hand under the front of her skirt. My fingers pushed between her pussy lips and sought out her clit and I started to rub her in the way I know she loves. Jen whispered to me that I was mean so I rubbed her some more. I’m pretty sure I could have made her cum –and had it been any other day I probably would have, but she told me that she was getting close to cumming so I stopped rubbing her (although left my fingers on her pussy). This was a fairly remarkable display of self-control from Jen as it is usually only Mike who can easily hold back, but I guess her upcoming ‘nuptuals’ with Mike had been anticipated for so long that she wanted to do things right.

I continued to make things slightly difficult for her at lunchtime – after we’d eaten, I dragged her back to my lab and took her in to the storage cupboard. I really wanted to eat her, but had promised Mike that nothing other than my fingers would touch her pussy from the time we left the house that morning so all I could do was finger and frig her. I once again got her quite close to cumming (not too close though as we didn’t want any accidental orgasms). So it wasn’t entirely one-sided, I let Jen finger me until I was close to cumming and got her to stop, which meant we both left the cupboard in a horny state. I didn’t do anything to Jen on the way home other than have a whispered conversation with her about what she and Mike were about to get up to.

We had a quick dinner and headed off in to the bedroom. I was only going to be watching them so I pulled a chair up beside the bed and fished out a dildo to play with. Mike stripped off and then slowly helped Jen out of her clothes. The plan was to let them slowly explore each other’s bodies and gradually work up to having sex over a few days. As Mike had participated in the watersports in the garden earlier in the week, Jen had agreed to go along with one of Mike’s fetishes and she pulled on a pair of seamless opaque tights (without panties) so he could kiss and caress her legs. Mike had done this to her (and me) many times before, but this time he was finally allowed to touch all of her and as he lay beside Jen kissing her, his hand stroked up the inside of her thigh and around her pussy. He broke the kiss and said that he wanted the first proper touch (I’m not quite sure how the times Jen had humped against his cock didn’t count as a ‘proper’ touch) he wanted to use his mouth, so he kissed his way down her body (with a brief detour to each of her nipples) until he was kissing her mons through the tights. Even though Mike has been desperate to fuck Jen ever since I first met her, he asked if she was sure it was time and she nodded. He lowered his mouth back to her mons and kissed down to her pussy, placing gentle kisses up and down each side of her pussy and then started kissing her square on the lips. Between kisses, Mike told us that he could smell and taste Jen through the tights (but she usually gets quite wet so this wasn’t really surprising). He pushed her legs slightly further apart and started to lick her more forcefully – it took a little longer as the tights protected her from the full force of his tongue, but after a while Jen started mewing and Mike just held on to her legs and carried on eating. He noticed that she was playing with one of her breasts and asked her to stop so that he could make her cum by himself. Jen pulled her hand away and told him that she wanted to cum – if it had been me he was eating, this would have usually meant he would back off and just tease me until I was desperate to cum, but he didn’t want to do that for their first time and he resumed licking her. Jen mewed her way to her orgasm and Mike lapped away at her crotch and then kitty kissed her (this wasn’t as effective through the tights, but it allowed him to sample a little more of her juices).

He crawled back up so he was lying over her and they kissed deeply. Jen wrapped her arms around him and as he pressed his cock against her crotch he told her that things felt very damp down there (which she blamed him for). They kissed a little more and Jen said that it was now her turn to experiment. Mike sat up and pulled Jen’s tights off – I thought he was going to at least caress her bare pussy but he just admired it and told Jen that he would taste her again in a little while. Jen sat up in front of Mike and reach out slowly for his cock. This was the first time she had actually touched it with her hand (other than occasional accidental brushes) and she gently wrapped her fingers around it and commented on how it felt hard and soft at the same time in a similar way to our favourite silicone coated vibes (which is why I like them as they feel like a real cock – just with the added ability to vibrate!)

Jen started to stroke up and down and Mike gave her a few tips about how much pressure to use and not rubbing too much on the glans (he is very sensitive there). Jen was obviously still learning but she seemed to get the hang of it from the expression on Mike’s face. She experimented a little and Mike told her that it probably wouldn’t take too long to make him cum if she continued like that (which is better than I managed the first time I stroked him, but Jen did have the advantage of having seen me play with Mike many times). Jen got Mike to lie down and she lowered her mouth to his cock. She took the head in to her mouth and bobbed her head up and down. She gradually took more of his cock into her mouth and started to lick him with her tongue as well (she *has* read all of the entries on here so she knows what he likes). Mike said that he was getting very close and Jen briefly broke contact to say that she wanted him to cum and then resumed sucking him. Less than a minute later, he told her he was just about to cum and she hummed encouragement just before Mike let out a ‘aahh’ and pushed in to Jen’s mouth. I saw her head jerk up a little, but she didn’t break contact and continued to suck and stroke him. Mike emptied his cum in to her mouth and then told her to slow down - which she did – but she didn’t pull her mouth off of his cock until she had swallowed all of his cum.

Even though Mike knew that Jen didn’t mind the taste of his cum, she usually eats it out of me so he was a little surprised that she had swallowed the whole load on her first time making him cum (but he enjoyed it). Jen climbed over him and pressed her pussy against his cock, then leant down on him so they could kiss. Mike said he could taste himself a little (which he doesn’t like, but he couldn’t really complain) and his hands went to Jen’s ass to pull her against him. She pointed out that he usually didn’t go soft when she was rubbing against him but he retorted with the fact that she usually hasn’t just sucked him off. Mike told her that as she had now tasted him properly, he wanted to do the same and after another brief kiss he rolled Jen on to the bed and mounted her. He kissed her nipples for a few minutes, gave her a final kiss on the lips and then moved down between her legs. Now that she had removed her tights he could see her pussy properly (not that he hasn’t seen it before) and he started to kiss around her thighs and over her mons. He didn’t tease her for long before he moved his kisses on to her pussy and then started to lick her.

He gave her a similar treatment to the first time he ate me and although he mostly concentrated on her pussy, he also swirled his tongue over her ass a few times. Mike took a little longer this time and gently lapped at Jen’s pussy and clit for a good 10 minutes. It didn’t look as if he was trying to tease her and backing off, he was just taking his time and exploring her pussy thoroughly. Once again, Jen started to play with her breasts as she got close to cumming but Mike asked her to stop and she did. I could see that he was grinding his cock against the bed (and I correctly assumed he was hard again by this point). As Jen’s mews became more insistent, Mike held on to her and swirled his tongue around and inside her pussy and over her clit. She told him she was close and I watched as he kept his face glued to her pussy and ate her. Jen held on to the back of his head (as if he was likely to pull away now that he finally had his tongue in the pussy he’s wanted for so long) and she let out a series of interesting (and sexy) sounds as she came.

My fingers had been busy in my pussy a few times during their extended display but I’d decided that I would cum while watching him eat Jen properly for the first time. I had also decided to forgo the vibrator as I didn’t want to make any noise that would interrupt them. I had my legs over the arms of the chair to give myself easy access to my cunt so I could concentrate on the view. Seeing the two people I love the most finally doing things together was as exciting and arousing as I had expected it to be, but I’m ashamed to admit that I felt a little bit jealous as it meant that they were no longer just mine (we were now all each other’s) but I had sort of expected that so ignored it (or to be more precise I just continued to distract myself with two fingers in my pussy and two on my clit). I didn’t manage to cum before Jen did (which was probably a good thing), but Mike was still kitty kissing her and lapping up all of her juices when I did cum and a few whimpers escaped me. Jen looked over towards me and Mike lifted his head from Jen’s pussy to ask if I had enjoyed watching them. I could still feel my pussy pulsing so I just nodded and let out a few pants and told Mike to finish bringing Jen down slowly.


  1. Has Jen ever been with a guy either orally or vaginally?

  2. Is this Jen's first time 'going all the way' with a guy?

  3. Jen had a few boyfriends back in school (before she came out), but hadn't done anything too much with them (nothing beyond letting them get to fondle her breasts) so the things she has been doing with Mike are all heterosexual firsts for her (of course she had almost all of her 'actual' first times with me.

    Mike was quite jammy in getting to take another girl's (hetero) virginity, both in the oral and vaginal sense. He has a relatively good record at this, but it's going to be difficult for him to find anyone else who will offer him their cherry!