Exploring with Di... a Year Later

Well, with being on active duty with the Marines, I did not get home often. Di found her a man and she was now engaged to be married. We sent letters back and forth so I knew how things were going. We even talked on the phone once in a while. I knew her and her new man were having sex and he knew she was not a virgin. He just did not know who it was that had taken her cherry and she would not tell him Seemed like he was a little on the jealous side.

I got to take some leave around Christmas and I head home. The drive takes about 12 hours with gas, bathroom and food stops. But I make it home safely and my Mom welcomes me home. The Christmas tree is up, my brother and sister are still sound asleep when I get there. I climb onto the couch and fall fast asleep.

The next morning, I get up, have some breakfast and go over to see Di, see how she's doing. My sister had said she did not like the guy Di was engaged too. Said he seemed to be very bossy and jealous of her friends. As I get to Di's house across the street, her mother opens the door and I get a hug from her. Di comes into the kitchen in just her baby doll nightie, not the first time I have seen her this way. I think her mother knows we had been intimate. BJ, Di's mom makes me a cup of hot tea and we sit around talking about me and Di's upcoming wedding the next summer. Her Mother leaves to go to work as her Dad had left before I got over there. Her sister came into the kitchen dressed and left with her Mom. That just left me and Di in the house.

We started talking and I told her I wanted to know everything about her future husband. Boy did I get an earful. Yes, he was jealous of her friends, kept wanting to know who her first lover was and was he better or worse the he was. She never would answer him, which mad him mad. We moved from the kitchen into the living room and took seats next to each other on the couch. Yes we kissed and she told me she missed me. My hand was on her bare thigh and it felt good to be feeling her skin again. I asked her how the sex was with him and she replied he was not the most enthusiastic lover. But her had asked her for something she was not prepared to do just yet, he wanted anal with her.

I had moved out of the barracks and was living on my own off base. So I was able to bring gals to my home and not have to stress of finding where to take someone for a little play time. One of the gals had being seeing had asked me to do her ass one night. So that had been a first for me, and I told Di about that time. This is when Di shocks me, she tells me, that I took her cherry, i was the first guy she gave a hand and blow job too and first man to eat her out. So now she wants to to be the first to fuck her in the ass as well.

I ask her about how big her future hubbies cock is, and she tells me its a little smaller then mine. Mine is about 6 1/4" when I am super hard. This info make me feel good about my manhood. I ask her why she wants me to be the person to take her ass cherry, and her reply is that she trusts me and know I would not hurt her and listen to her.

I ask her when and where should we go to enjoy this special time. She says she would like to find a hotel room like last time and for us both to have fun. My hand has moved up and is now slowly caressing the bottoms of her nightie. We kiss again and I come right out and tell her I want to eat her out right there and now. She gets up quick and says she needs to lock the kitchen outside door so we do not get disturbed. Sounds like a plan to me.

When she gets back to the living room she has already taken off her jeans and panties. I get a treat and see that she has now trimmed up to a nice landing strip. My smile says how much I approve. she takes her seat on the couch, spreads her legs nice and wide and tells me to please enjoy lunch...Which I dive right into, after she cums for me, she says her turn and tells me to stand up. Of course I willingly do. She pushes down my jeans and drawers in on push and my hard on pops into view. She greedily latches onto it, and starts to give me a great blow job, She has had some practice over the last year. I cum and she surprises me even more by swallowing every drop.

I collapse onto the couch next to her, both naked from the waist down. We cuddle, and I tell her this and whatever we do tonight has to remain our secret, which she agrees to.

That evening we go out to dinner together and then stop at the local pharmacy so she can pick up a few things. She gets a box of condoms and a tube of KY. when she gets back into the car, she says the cashier told her to have a good time...LOL

We head to a hotel, which is veteran friendly and will not ask a lot of questions, especially to a Marine in uniform and his gal. We get a room and get inside, close and lock the door, close the curtains and kiss deeply. We start getting undressed and head into the shower to get nice and clean. She then tells me she had done something she had never done before, she gave herself an enema, saying she wanted to make sure she was clean.

Now with both us naked we climb onto the bed, and make out some. I fingering her pussy as she strokes my hard on. I reach for the KY and place some on my finger and reach down and slowly start to rub her rosebud. I ask her to roll over which she does. I apply some more KY to both my finger and between her butt checks and I start to finger her ass.

I slowly slip one finger in slowly and ask to make sure I'm not hurting her. Do not want her first anal experience to be a painful one but we all know there is some pain. After a bit of one finger I add more lube and slip in a second finger and ask her to get on her hands and knees.

I withdrew my fingers from her butt as she gets into the doggy position, Once there I add more lube and go back to fingering her. She has reached down I notice and he rubbing on her clit. I reach for the box of condoms and she tells me no, she wants to feel it bare. I'm like OK bare it is.

I get be behind her and slowly start to slide my very hard cock into her virgin ass. This being the second time I have had anal sex with a woman. I take my time as it goes in stopping along the way to let her adjust and get use to the anal invader. Once I get all the way in, I stop and ask how she is doing, she has a three word reply; "Fuck my ass".

what is a man to do, but obey his lovers request. I start to slowly fuck her picking up the pace as I go. I feel her hand reach up and touch my cock as it goes in and out of her ass. As I am fucking her, I can feel myself getting close to busting a huge load into her rectum and tell her so. She just moans and I slide in deep and cum, and man did I ever.

I think she has had her own orgasm, as I slowly pull out, cum and lube dripping out onto the towel I had laid down. Di collapses onto the bed and I lay down next to her, I ask if she is ok and she replies with a huge smile and says; "Hell yeah, that was amazing".

After about 15 minutes she does into the bathroom, closes the door and I head to the sink to clean up. I throw the used towel on the floor under the sink. Di comes out of the bathroom still smiling and tells me thank you and that she will now let her future husband fuck her ass as well.

We go back to the bed where we make love one more time before we both get dressed and head home. Three months later she gets married, and we still stay in touch to this day, many years later.

And yes we have been together a couple times when I was home on leave, but those are another story for another day.