I have no idea what I am doing or what to do.

[HarryWest]

I believe I'm getting used to the feeling. Things have been going better than previously.

I've learned how to relax myself almost completely and really trust in Jess fully. The stretching sensation is still getting to me every time, even when Jess goes extra slow. It feels like I am being torn apart.

Then sometimes when Jess is only 2/3rds within I get this incredible feeling, a rush and just cannot stop myself from orgasming.

Jess says I'm just too sensitive, however I am enjoying myself.

[Alice Rogers]

Sounds like you are finding your proverbial feet on this one hun, it is worth mentioning that relaxing or not you really can't have too much lube to hand in these early days.

Sounds like you might have the potential to be multiorgasmic from receiving penetration, it is a true gift that I cherish and thank the heavens for!

Have you tried controlling the penetration by being on top and basically penetrating yourself? That's my fave way to start a lovemaking session even if we switch up later, you will have total control over pace and depth and if you think you are going to come too soon you can lift yourself off.

Honestly here I think it's worth mentioning that from personal experience the 'bottom' should probably dictate the pace until all the kinks have been worked out.

[Rotika]

New here. Just read your story. I think you're going to have a great relationship. You sound like you make a very cute / honest couple. Not just for the sexual part. But it really sounds like you're both putting a lot of effort into making this work. I wish you both the best together.

[HarryWest]

Have you tried controlling the penetration by being on top and basically penetrating yourself? That's my fave way to start a lovemaking session even if we switch up later, you will have total control over pace and depth and if you think you are going to come too soon you can lift yourself off.

Whoa, I'm only new at this stuff. Acrobatics are really not my thing and I have no idea how I could do that without Jess turning me into a human lollypop.

[Alice Rogers]

Whoa, I'm only new at this stuff. Acrobatics are really not my thing and I have no idea how I could do that without Jess turning me into a human lollypop.

LOL, I meant kneeling above her while she lays down, you have good strong thigh muscles to control the depth and angle that way, it gives you control to help guide things into place without any discomfort.

[HarryWest]

LOL, I meant kneeling above her while she lays down, you have good strong thigh muscles to control the depth and angle that way, it gives you control to help guide things into place without any discomfort.

Gave things a go as advised. Actually Jess went first and showed me how to do it. How to guide and position my legs etc.

We have mostly been going at things in missionary or doggy up until now. I really don't have that good of balance when I tried but I did find I had better control as you noted.

Jess said that she did not think the position (kinda female superior) would have been of interest to me and so had never suggested it.

[Alice Rogers]

Gave things a go as advised. Actually Jess went first and showed me how to do it. How to guide and position my legs etc.

We have mostly been going at things in missionary or doggy up until now. I really don't have that good of balance when I tried but I did find I had better control as you noted.

Jess said that she did not think the position (kinda female superior) would have been of interest to me and so had never suggested it.

I am glad you had a little success with it, if you enjoy this position then by all means stick with it, but it IS a really good way of giving a partner who is new to being on the recieving end more control.

Doggy can be good too, ask Jess to stay still and let you do the moving, that will give you more control too.

Alice
xx

[HarryWest]

Doggy can be good too, ask Jess to stay still and let you do the moving, that will give you more control too.

Yeah, Jess is the sort who likes to grab hold and have at it.

The most comfortable I have found is the "Ankles Up" position with pillows underneath me.

Sure it gives Jess all control but it just feels sort of right. I get to watch her face.

[Alice Rogers]

Someone is starting to enjoy himself I suspect *hugs*

Alice
xx

[Natalie]

If you cannot handle a penis then find another person to date. I would have to say, though, that she is a "she" irrespective of the fact that she is packing that "thing" around.

[HarryWest]

If you cannot handle a penis then find another person to date. I would have to say, though, that she is a "she" irrespective of the fact that she is packing that "thing" around.

Why? It is a part of who she is.

I may be having difficulty accepting in the physical sense (who wouldn't first time round), but Jess is Jess, a wonderful caring person, beautiful and fun (and who also barracks for the same football team).

Why would I give that up just because she has an extra appendage other girls don't "generally" have.

I love her for who she is, not what she is.

[Alice Rogers]

If you cannot handle a penis then find another person to date. I would have to say, though, that she is a "she" irrespective of the fact that she is packing that "thing" around.

Ouch! He is doing his best and making good progress.

Props to you Harry for your patience and willingness to work at your relationship, shame there aren't more like you out there!

Alice
xx

[Kyra553]

Harry you rock for wanting to explore more and creating true emotional bondage. =)

So were we right about the amazing feel after you adjusted to it ?

[HarryWest]

So were we right about the amazing feel after you adjusted to it ?

I'm not sure if I know how to explain myself? The "feel" is amazing, but I am still adjusting.

I know I'm enjoying the sensation of penetration, the rush and fullness of her within me, the closeness of the experience.

But the pain after just a few short strokes is still prevailing.

[Kyra553]

I'm not sure if I know how to explain myself? The "feel" is amazing, but I am still adjusting.

I know I'm enjoying the sensation of penetration, the rush and fullness of her within me, the closeness of the experience.

But the pain after just a few short strokes is still prevailing.

Thats a good sign though! Your adjusting and it takes time to truly "open up". 

Do you have any thoughts about your relationship now compared to your first post? 

[MrKarl35]

Anal can be a lot of fun, both giving and getting. It can take some practice to hit your stride but it sounds like you are off to a great start. The most amazing thing I see here is how well the two of you are communicating. Keep practicing with plugs and touching your self at the same time. The feeling of P-Spot stimulation can be super intense, with some practice you will find that "edge" you can ride (pun intended) and stay hard but not finishing too quickly. Have fun, woah... I need to take a cold shower

[HarryWest]

Do you have any thoughts about your relationship now compared to your first post? 

Hmm, that's a hard one as I have not really explained our emotional connection and most of my posts have focused on the sexual nature between us, which was most pressing at the time when I made my first post.

I have known Jess for about two years now but we only started dating in November of last which was about seven months prior to my first post.

We just met one day at a BBQ being hosted by a mutual friend. We kept running into each other of the next few months going to this or that get-together.

At the time that I met her I did not know of her past and it was not until a half a year later that see told me over drinks one evening of her "underlying" nature. I had thought her kidding when she said it and so it never sunk in at the time.

Then she invited me to come to her younger brother's wedding on her family's farm and we went swimming butt naked in the dam out back. And it was like "OK... she wasn't joking about that".

But I totally brushed past that and it was only a couple of more months later when I asked her out proper and things went from good/best friends to boy/girl-friend.

After that it's as I described in my posts. I totally forgot the whole situation. It just was as it was/is.

Then when I first posted here Jess and I had reached the stage where we were moving to more sexual stuff and I totally freaked as I realised what it entailed and I needed information and help.

Which I got. THANK YOU ALL!!!

But since that first post and now. While our sexual relationship has begun and is still growing. Our emotional commitment to one another has really firmed up. I trust Jess impeccably.

I mean sex is great. But I'm really in it for her.

So looking back I'd have to say things have most assuredly improved in our relationship.

[Alice Rogers]

So looking back I'd have to say things have most assuredly improved in our relationship.

You sound like that one in a million guys Harry, it affirms my faith in humanity that there are guys like you out there, I wish you and Jess all the best for the future.

Alice
xx

[Kyra553]

I'm very glad things have progressed positivity for you both. Jess is definitely a lucky girl to have found such a wonderful person to be with.

Definitely keep us informed! I love reading about you two. =). Hmm has Jess read any of this?

[HarryWest]

Definitely keep us informed! I love reading about you two. =). Hmm has Jess read any of this?

Jess knows I have been posting to, and getting advice from, here. I have no issue with Jess reading what I have posted, it is mostly the same as what I have spoken with her about.

As far as I know she hasn't and is letting me have this as my little avenue of personal space.

But I have shown her, and discussed, a few of the comments I have received etc.