Assuming everything is going to plan, Jen and I should be starting our ceremony right about now…
I forgot that I’d promised to write about Mike’s first times, so will do that now. Long term readers will know that I was the third girl that he’d actually slept with (or his third proper girlfriend as he puts it). You already know about our first time (as well as the subsequent ones – and if you don’t, they are all detailed in previous entries), so I’ll be leaving those out and concentrating on his ‘early years’).
Mike’s first girlfriend was at school with him. She was called Sally, and like me, had long dark hair. They actually started off very slowly and had been sort of flirting for a while, had spent an evening kissing at a party, she had then made out with another guy a week or so later (which he was rather upset about) and then when they talked about it and he told her that he liked her, they ended up getting together.
Sally is where his opaque tights fetish comes from (I think) – as she wore these most of the time when she wasn’t in school uniform (and often when she was). She almost always wore skirts, although quite a lot of the time they were ankle length, flowing skirts, but whenever she sat down, she would pull the material up to her knees and Mike would admire her legs.
Sally had large breasts – not quite as large as mine, but Mike thinks they were fairly close. Now Mike isn’t a breast man, but as a 16 year old boy, he was more than happy to play with her breasts and he got her top off a number of times to kiss, lick and fondle them. They did this outside a few times in the woods just by Mike’s house. One evening he had taken her out for dinner (he can’t remember if there was a specific reason for that) and had stopped in the woods on the way home to make out. He soon had her top and bra pulled up and his face buried between her breasts, but this time he also got his hands under her skirt (which he remembers was one of her long dark ones). He got his hands down the back of her tights and into her panties when she told him to stop and said they should head home. He thought that he had gone too far, but she didn’t seem to be angry and when they got in, they went straight up to his room (he says that he literally dragged her past his parents so they didn’t get caught up in a conversation about their meal).
They resumed their kissing on the bed and he ended up on top of her. She could feel his cock pressing against her through their clothes and after a few minutes, Mike pushed his hand down her body and between her legs. This was the first time he’d touched her crotch (with his hand) and he rubbed her through her tights and then when she didn’t object, he pushed his hand into her tights and found her wet, warm pussy. He didn’t really know what he was doing as this was the first time he’d actually touched a pussy, but he knew what he wanted to do as he’d seen enough porn already. He pulled her tights and panties off, spread her legs and crawled between them. Sally seemed a little nervous about him getting such a good look at her pussy, but he didn’t look for long and quickly started to lick up and down her cunt. He had wanted to do this to a girl for years and he eagerly ate her. He knew enough to try and concentrate his licking around her clit (although he didn’t really know exactly where this was). Despite it being his first attempt, he made her cum and she had to push him away when her orgasm had ended (he was enjoying himself quite a bit).
It was now Mike’s turn and after they had kissed a little bit more (Mike had wiped his face clean of Sal’s juices), he rolled off her and she stroked the front of his trousers. With his help, she undid his trousers and got her hand into his boxers and he ended up cumming over her hand almost immediately. They kissed a bit more and Mike briefly fingered her – he was going to go down on her again, but it was getting late and Sal needed to get home. He did at least walk her back home and they had a long goodbye kiss – he tried to get his hands back into her tights so he could get her juices on her fingers, but Sal was worried about her parents seeing, so he wasn’t allowed to and had to be content with just the kisses. He ended up masturbating again later that night (once he’d got home and gone to bed).
Sal didn’t want to do this again for a while and their sessions went back to just kissing, although he was sometimes allowed to rub her through her tights or dry hump her. The next time something happened was in her bedroom – they were making out and when he tried to get a hand between her legs, she didn’t stop him and he soon had her tights and panties off. This time he started off by stroking her – although from his description, stroking might not be the right phrase as he was quite forceful and strummed his fingers rapidly back and forth over her clit. She had to get him to stop a few times as he was using too much pressure and in the end he crawled back between her legs and went down on her again. He had no trouble making her cum this way.
Sal had begun to stroke him while they had been kissing so he had been able to grind his cock against her lower leg while he’d been eating her. Once she had cum, he sat up and she took hold of his cock again and within a few strokes he came over her thigh and across her skirt (which was pulled up over her stomach). Once they got her cleaned up (Mike remembers using her panties to do this), he got to play with her pussy again (more gently) and he explored it properly. In most of the porn he’d seen, the girls had been shaved or partially shaved, while Sal had a reasonably large bush, so he couldn’t see as much as he wanted. They ended up being disturbed by Sal’s little sister knocking on the door and Mike quickly fastened his trousers (Sal only had to slide her skirt down and hide her wet panties).
One time at school, they did things together while hiding behind one of the buildings. He knelt in front of her, pulled her panties down, got her to hold her skirt up and he ate her. Once she’d cum, he got her to suck him off – Sal didn’t enjoy doing this much and really didn’t like having him cum in her mouth (which I don’t blame her for – it took me quite a while to get used to the taste).
On another occasion at Sal’s house, Mike convinced her to let him shave her. She was quite nervous about this, but he trimmed the hair with scissors first and then used her razor to finish the job off. Even though he had played with and eaten her a good number of times by this point, he now got to see her properly and he discovered that it was far more pleasurable (both for him and her) to eat her shaved cunt. He ended up eating her three times in a row (to three orgasms) as he found the sight so appealing. By the time he’d finished, he was pretty much ready to blow and he just asked her to open her blouse so he could cum over her. It didn’t take long until he came and he squirted his cum over her breasts. At his request, she massaged this in and they then used her panties (again) to wipe up any remaining cum.
Sal didn’t enjoy having a fully shaved pussy as she found it too itchy. Mike tried to get her to not wear panties, but she would rarely do this (especially to school) and so in the end they settled on only shaving her lips, so he could easily eat her, but letting the hair grow back on her mons and keeping it trimmed. They carried on fingering, jerking and eating for a few months – sometimes in the woods, sometimes at school and most often at one of their houses. A few times Sal’s sister interrupted them – she never caught them actually doing anything, they thought that she knew what they’d been up to (one time Sal had forgotten to hide her soggy panties and they think that her sister saw them).
Things carried on like this and they ended up completely naked together a few times (when they had a house to themselves for a few hours). Sal let Mike hump against her once or twice and it was clear that the next step was to actually fuck properly. Eventually the day came and Sal had told him to come over one Saturday while the rest of her family was out. They had already bought some condoms and after a brief bit of foreplay, Mike suited up and slipped into her. They just used the standard missionary position, but he remembers even now how amazing it felt. While he’d gotten a bit better at delaying his orgasm, he still didn’t last too long and came before she had started to feel too much. This gave him the opportunity to go down on her though and he made sure that she came twice.
They tried again a few days later and once again Mike came first and had to finish Sal off with his fingers and mouth, but he lasted a bit longer and she enjoyed the actual penetration more. Over the following weeks, they ended up fucking at pretty much every opportunity they had. Mike even convinced her to fuck while at school and they got used to Sal leaning forwards against the wall and sticking her ass out so he could take her. He usually just lifted her skirt up and pulled her tights and panties down just enough to get inside her and they would fuck like that. He rarely managed to get Sal to cum by just fucking her (he didn’t really understand that he needed to stimulate her in other ways at the same time), but she liked this as it was cleaner than him cumming over her and it meant she didn’t have to suck him off.
In the summer months, he convinced her to wear shorter skirts – sometimes with tights and sometimes with socks (white of course, but that was the uniform). This outfit made it particularly easy to fuck her as she could just lean forwards and he could pull her panties aside and get inside her. Pretty much whenever they fucked, he would always finger or eat her afterwards so she came as well (unless they were interrupted), so even though his technique was far from perfected, he wasn’t being selfish and made sure she enjoyed herself as well.
He remembers one time that she had a short skirt on (not indecently short – it was within school regulations), he fucked her and told her that he wanted to do it again or he wouldn’t give her panties back. Sal didn’t want to risk being caught so refused to do any more, and he actually kept her panties for the rest of the day. Looking back, he does feel quite bad about it, but he also found it an incredible turn on knowing that her exposed pussy was just under the hem of her skirt. She got them back after school and he ate her in the woods to make up for it and convinced her to keep them off for the walk back to her place.
They did have a scare at one point – her period was late by a couple of weeks and she really thought she was pregnant. She had promised him that if she actually was pregnant, she would let him fuck her without a condom on, but eventually her period came and he never actually got a chance to enter her bareback. They split up after about 6 months and she went off with another guy a few months later and Mike spent the rest of his time at school pining after her. They did manage to make up and become good friends, but never got back together other than a light make-out session at a party (nothing below the waist).
Mike didn’t have his next ‘real’ girlfriend (what he terms the ones who he got to sleep with) until his second year of Uni. He had a lot of female friends (and still gets on with girls really well), but always seemed to end up as the one they were moaning to about their boyfriend. Fortunately for him, this changed when he met Fiona, a small blonde girl (small both in height and body size). She was quite shy, but a very nice girl (from what he tells me) and it took quite a while for them to actually get together. He was her first actual boyfriend (she was very studious so was pretty much shunned by the boys in her school) and things moved very slowly between them even after they’d got together.
They progressed from holding hands (no, I’m not joking, holding hands was an actual ‘step’ for her) to kissing, and over time to him playing with her breasts through, and then under, her top. Fiona wore jeans most of the time, which frustrated Mike somewhat as he is something of a leg man (probably thanks to Sally), but she would occasionally wear a skirt for him. They finally made it to humping and grinding against each other, but never made it as far as either one of them cumming and Mike was getting very frustrated by this point. He really did care about her so didn’t want to force her to go faster than she wanted to, but at the same time, he was tired of playing with her and then going back to his room to jerk off.
They eventually progressed a little further and he was allowed to slide his hand into her jeans and play with her pussy – at which point it became much easier to make her cum. Fiona didn’t like the idea of him cumming over her though (and at that point, blow jobs were certainly out of the question), so the only way he was allowed to cum was to do it in his boxers. Despite the slow progress, Fiona seemed to be opening up and enjoying their fondling (and especially her orgasms) more and they had discussed taking things further and actually having sex.
Their 6 month anniversary was coming up and Mike had saved up to take her out for a nice dinner and she had even agreed to wear a dress. With the dinner over, they went back to her room and (as usual) ended up on her bed, kissing. Fiona ended up on top of him and he pulled her against him, trying to slide her dress up a bit each time she rubbed back and forth. Eventually his fingers found the hem of her dress and he worked his hands under it, down the back of her tights, into her panties and onto her ass. This gave him a much better grip and he pulled her against him as he ground against her. They ended up rolling over and Mike pushed her top and bra up so he could suck on her breasts while he used his thigh between her legs (and rubbed his crotch against her leg).
He pushed a hand into her tights and panties, fingered her a little and then sat up to pull her tights down. He’d never actually seen her pussy before and was greeted with the sight of her pink, wet lips and pubic hair matted with her juices (not that she was absolutely soaked, but he had smeared her juices over her when he’d been fingering her). She didn’t have a huge amount of hair and it was dark blond in colour, so didn’t completely hide her cunt, but Mike was now really used to shaved pussy from his advanced porn gathering & watching so he was a little disappointed (even though he knew from touching her previously that she wasn’t shaved).
Fiona was quite embarrassed that he was looking at her and she was really surprised when he moved down between her legs and started licking her. He still remembers that he didn’t like her taste as much as he liked Sal’s, but he was still back doing his favourite thing and he carried on eating her until she came. He moved up her body and tried to kiss her, but she made him wipe his face clean before she would let him kiss her (what sort of girl won’t even eat her own pussy juice?). He told her he wanted to make love to her and she said that he could, but he had to use a condom. Naturally, Mike had been carrying some around for a while in the hope that he was going to eventually get to sleep with her so he quickly fished one out of his jacket, pulled his trousers off and rolled the condom on.
Fiona was quite nervous and Mike had the sense to not try and rush things too much (even though he desperately wanted to fuck her, he did also love her). They kissed a bit more and he rubbed against her, then rolled onto his back and pulled her on top of him. They carried on kissing and he once again held onto her ass and guided her back and forth, slowly moving his cock down so he could position it by her pussy. When he was in place, he reached around and spread her pussy, then pressed the head of his cock against it. He told her to press back slowly and after a couple of attempts, they got lined up enough for him to slide the head inside her.
He slowly worked his way into her, a little more at a time until he was pretty much all the way into her and then he guided her back and forth in time with his movements. She felt quite tight, but he at least lasted longer than he had with Sal due to a number of years of additional practice (admittedly through masturbation, but he could at least hold back a bit now). He had dreamed of fucking her until she came a second time, but the pleasure of being back inside a girl ended up being too much and he ended up cumming. Fiona didn’t mind (and she wasn’t used to cumming more than once in an evening anyway) and he got her to stay on top of him with his cock buried in her so they could enjoy the feeling. He only pulled out when he started to go soft and once he had cleaned himself up, they lay beside each other and snuggled.
He still wasn’t allowed to spend the night with her, but now things had progressed that far, they had sex a few more times that week and she even let him eat her (she found this rather distasteful, but the fact that he always made her cum seemed to offset this). Fiona ended up going on the pill and Mike was finally allowed inside her without a condom on and he enjoyed this feeling even more. It took Fiona a while to get used to leaking cum after they’d had sex and Mike wasn’t too keen on eating her when she had his cum in her, but he always did this as she couldn’t cum just from him fucking her.
He finally had the revelation of getting her close to cumming and then having sex – usually he would do this by eating her beforehand until she was really close to cumming, but as they became more practiced, he started to play with her clit while they fucked as well and found that he could draw things out more. Fiona was still fairly conservative though and the most he could really get her to do was to occasionally go on top – sometimes sitting up properly so he could play with her breasts as she rode him, but most of the time they just used the missionary position. He never got her to shave her pussy (or let him do it), but as her pubic hair was sparser than Sal’s, he didn’t mind this too much and still ate her as often as she would let him.
He remembers one time when they were in the middle of sex and some of her friends knocked on her door. Fiona wanted to stop but Mike carried on moving in her and ended up making her cum while they were chatting outside. He couldn’t get her to do many other adventurous things though and it became clear over time that while he really liked her, they were fairly incompatible, both sexually and in other aspects. Eventually they broke up – at the time, neither of them was happy about this and they almost got back together a couple of times, but they realised that they were better off as friends (although Mike would have preferred friends-with-benefits).
Following Fiona, Mike had another dry spell until he met the love of his life (me) and he got to corrupt me in new and interesting ways that he had dreamt up while masturbating. I’ve already detailed our first time near the beginning of the blog as well as his first time with Sue (who wasn’t a virgin, so it doesn’t really count in his eyes). We’re still undecided if Sara counts as a virgin – he definitely took her heterosexual virginity, but she’d been with a few girls before that. All things considered, I don’t think he can complain too much with having taken 3 ½ girls’ ‘flowers’ and while I’m a little jealous that they got to fuck him before I did, I’m also thankful that he learned from them (and from masturbation) and can now last much (much) longer than the couple of seconds it took Sal to make him cum the first time she touched him!
My apologies for how this entry turned out – I wasn’t feeling too well when I wrote it and while I’m writing about what Mike has told me, I had hoped that it would come out a lot more sensual/erotic than I think it did. Technically I should try and rewrite it, but if I went back and fixed things I’d never stand a chance of catching up!