Roleplay fears and past relationship sexual trauma

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I love my partner and feel like he is the best partner I
have had. He is supportive, communicative, great at words of affirmation via
text, smart, and we have great rapport. My last partner was hot-and-cold and
treated spending time with me as a chore. He didn’t even really try to get to
know me and the partner before that had an explosive temper.
 
The partner with the explosive temper was my first real
boyfriend. We were together seven years. When we did have sex, he would scream
at me, berate me for being shy during sex or not doing things he liked even
though he would give basically no direction nor communicate what he wanted, and
would make fun of me for things I liked sexually.
 
In my last relationship, I would cry at the beginning of the
relationship due to all the fears I acquired in the relationship before. By the
end, we were able to get to a point where I think our sex life wasn’t bad
though I felt like I still didn’t know what I was doing and that partner was
hard to do anything with since his body was sensitive all over the place.
 
For my current relationship (3 months), I am experiencing some
issues. We only get the chance to have sex every other week. So, when he first
sees me, he is already in the mood, but I am not feeling it because I need a
bit of emotional intimacy to feel into it. I kind of feel like a piece of meat
when he tries to initiate when he first sees me without even a chance to just
reconnect. Also, because we haven’t had sex in a while or gotten the chance to
cuddle in almost two weeks (we do see each other multiple times a week, but
don’t get the chance to be in a private setting often), my brain for some
reason resets and it feels like I am with a stranger, so I feel uncomfortable.
What I really want is to have romantic/tender moments or to feel connected
(like having sex after we talk deeply for a while and the mood becomes
romantic), words of affirmation, and to be kissed softly and then more
passionately and that leads up to sex or to have a day where I am getting
romance and then by the end of the day we have sex.
 
When he does come onto me, I do still continue with sex and
pleasure him (he does, of course, pleasure me to orgasm, too), and can get into
it, but it’s not as enjoyable as if I felt all in. I know he is newer to sex
and hasn’t had it for a long, long time. From when we first started dating, he
has gotten much better at sex and I know he is still learning. He told me last
night that while having sex, he was picturing me as a cheerleader and that
helped him enjoy it more. He said that he wants to do roleplaying. Roleplaying
is something for me that leaves me with so much fear. It combines my fear of
public speaking, of being judged, of being out of my element, not knowing what
I am doing (I can’t think of what a person in x role would even say or do, or
what would be sexy about a given scenario), and the chance to disappoint
someone. I think I am still haunted by how sex was with my first partner. I
know I have a much, much easier time in trying/doing dirty talk when I am 100%
in the mood. I told him last night that I think it would be easier for me to
feel more comfortable doing it if it felt less like we are rushing into sex and
there was more romance. He said that he will work on it.
 
We are also running into other issues.:
\- He was screamed at during sex in his last relationship and
his ex forced him to have sex with her when he would have migraines/be in pain
and berate him when he wasn’t in the mood or couldn’t get it up, so he has
learned to associate sex less with his pleasure.
\– Due to this, he faked it before with other partners (and
twice at the beginning with me), but also gets a bit in his head during sex and
feels guilty receiving pleasure as his ex made him feel that it was selfish. He
has never cum during sex with anyone and said that I am the first partner where
he actually feels anything during sex (blowjobs, handjobs, intercourse).
\- He has a fear of pregnancy (I do as well), but even when I
am giving him a blowjob, he is afraid of pregnancy and can’t fully enjoy it.
 
Since he learned that sex was only about the pleasure of his
partner, he would push through any pain during sex (the first two times — he
initiated both) and not let me know he was not feeling good. We have had a talk
about how I do not want him to be in pain during sex nor feel discomfort and
that sex should be enjoyable for both parties. I have also told him that I
don’t want him to feel guilty (easier said than done) when I am pleasuring him
as I am enjoying pleasuring him because I like that I am making him feel good.
He said he is still working on things on his side.
 
What can we do to make things easier and work through our
issues?

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