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Positions: Placing a pillow under the rear of the person being penetrated can help them relax and Lady want hot sex OH Ashtabula 44004 the angle of penetration more comfortable.
Or, you can consider having the person being Horny housewives Bahamas east on top so that they can control the speed and depth of penetration. Go Slow and Communicate: During sex play, ensure that the person penetrated is in control, and communicating to the penetrating person how things are going: how fast to go, how deep to go, when to ease up, and so on.
Secondly, do not just ram the penis or toy in! Start with the head.
If that is OK, ease it in an inch or two farther and check comfort levels. Take as much time as you both need to adjust to each new sensation.
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If any of the partners are relatively inexperienced at this, take the pressure off by giving up on goals and concentrating more on enjoying the process. Like so many things worth doing, it may take several tries before everyone is happy with the experience.
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Maybe use just fingers or fewer fingers until it is comfortable.