Engagement Sex

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Surprise is revealed before Melissa & Bobby get engaged.
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I've been with my girlfriend for over a year now and love her so much. She is cute, funny, and really sexy. We have a great time and we love to play around a little sexually, but Melissa is a conservative girl and has told me many times that she won't go all the way until we are engaged. Up until recently, I had only seen her naked breasts.

God! does she have wonderful breasts. Melissa is about 5 foot 8, 130 pounds, and has size C cup breasts. They are implants, but you can hardly tell, and they feel so nice. She said she was born flat-chested and got her implants to make her look as sexy as she felt. I can't blame her, and I'm not sorry I get to be the one to play with them occasionally. Once in a while she lets me suck on her nipples, which drives her wild! She has also rubbed my cock through my shorts, but that's it for us sexually. I really wanted more, but was willing to wait.

About a month ago I decided I was going to propose. I just couldn't see myself being with anyone else in my life. We are so connected emotionally. After getting the ring, I decided to propose at a really nice restaurant that we like, and then take her home for a quiet romantic evening.

At the restaurant, I worked it out with the waiter to deliver the ring with her desert. Melissa was overcome with joy when she saw the ring and tears came to her eyes. "Oh Bobby," she said. "I love you so much, and I can't wait to be married! But before I accept, I need you to be sure you really want me. We've never made love and you might not find me very good in bed. I think it's time we went a little further," she said with teary eyes and a big smile.

Hearing this just made me lover her more. She was always worried more about me than her. I said, "Honey, there isn't anything in the world that would make me not want to be with you the rest of my life. You are so smart, cute, and sexy. I really couldn't imagine not being with you regardless of how our first time goes."

After desert, we went back to my place and I poured some wine and started some soft music in the background. While she went to freshen up, I also started a fire and placed a few pillows on top of our fuzzy rug.

Melissa came out in this almost sheer black babydoll with a plunging neckline that barely covered her tits, and panties! My jaw just dropped and I didn't know what to say. I was stunned. She came over to me and kissed me deeply. She was such a great kisser. As we kissed, she unbuttoned my shirt and through it to the floor. She kissed my neck and ears, and then moved to my chest and began to lightly lick my chest and suck on my nipples.

This drove me wild and I couldn't wait to return the favor. But Melissa kept going. She then knelt down on the floor and slowly unzipped my pants as she looked up at me with a big smile on her face. All I could think of saying was, "I love you," and she winked back. She then pulled my pants down and took off my socks and through them to the other side of the room. I was left standing in my boxers with a growing boner.

I couldn't wait for her to touch it. This would be the first time and it would be so great! I really didn't know what she was worried about. She was so sexy and driving me wild! Melissa then began to kiss my cock through my shorts, wrapping her lips around my shaft and squeezing. I just got harder from this and I could tell she was having some fun. She eventually tugged at the bottoms of my shorts and my cock finally sprung free as my shorts hit the floor.

Melissa just stared at it for a moment and I was worried she was getting second thoughts. Thank God she didn't! With my cock pointing directly at her face, she leaned forward a little and kissed the head of my cock. She then got a little closer and reached behind me and grabbed my buttocks with each hand, and then slowly took the head of my cock in her mouth. I was ready to explode right there! It felt so good to be in her mouth.

Melissa started swirling her tongue over the head as she took more of me in her mouth. She got about half-way, and then slowly pulled out and swirled her tongue again. It felt awesome! After a few more strokes, it seemed she was getting the hang of it. She then went a little faster and grabbed my cheeks to pull me into her mouth more as she went forward and then back. It was just the way I liked it. After a few minutes more when I didn't think I could take much more of this before I came, she suddenly stopped and looked up at me.

She said, "Bobby, I love sucking your cock. It's so beautiful and hard. I've wanted to do this for so long. Baby, I want to taste you. I want you to cum in my mouth," she whispered, and she began to suck me again. Before I could say anything, I could feel my orgasm coming. As I panted with each stroke, she gripped my ass tighter and began to suck harder and faster. I couldn't restrain myself much longer. Melissa was now taking most of me in her mouth and sucking me like she was starving for my cum. I didn't take long and I let out a loud moan and unleashed several streams of cum into her hungry mouth.

Melissa kept sucking until I was finished and it seemed she swallowed most of my cum, with a little left on the corners of her mouth. I eventually began to soften and she finally let me out of her mouth. She looked up again with those cute eyes and I just adored her. She got up and put her arms around me and then gave me a peck on the lips and said, "How was that?" with a big smile.

I said, "Amazing!" and leaned forward for another kiss. This time Melissa opened her mouth and gave me a full kiss. No girl had ever done that to me before after I came in their mouth, but Melissa had swallowed my cum, so there wasn't really much left to taste. Although I did taste something kind of sweet, it was a lovely kiss and I couldn't wait to return the favor.

Melissa then asked me to lie on my back, and as I did, she straddled my waist and began to remover her top. Her lovely breasts popped out as she took her top off, and then she leaned forward for another kiss. We kissed passionately again as I fondled her tits, and after a few minutes, she leaned forward and moved her right nipple over my hungry mouth. I loved it when she did this once in the past, and I eagerly flicked my tongue out at her nipple and then took as much of her breast into my mouth as I could.

Melissa moaned as I licked and sucked, then moved the other breast over for some attention. After a few minutes, Melissa whispered in my ear, "I am so wet. Do you want to lick me?"

I stopped sucking on her beautiful nipples and replied, "I've been dreaming about eating your pussy for so long honey, I can't wait to taste you."

"Well," she said, "this is what I was worried about at the restaurant. Are you still sure you want to be with me, no matter what?"

I wasn't sure what she meant. "Yes," I said.

She then stood up, straddling my chest, and slowly removed her panties. As her panties came down, she opened her legs a little and a cock and balls appeared between her legs. I just looked up stunned, and I could see the tears forming in her eyes.

Feeling bad for how I must have looked, I said, "Honey, come back down here. I'm sorry for my reaction. I just wasn't expecting that. Please, come back down."

Melissa sat back down with her cock resting on my belly, teary-eyed. "I wanted to tell you. I've wanted to tell you for so long, but couldn't. I was so afraid it would ruin our relationship. I love you so much. I just couldn't .....

"Shush...don't cry." I said, "It's OK honey. I understand. I love you too. I'm not sure what to do right now, but I'm willing to give it a try."

Melissa looked up with hope. "You'll give it a try!?

"Of course," I said, a little worried what this meant.

"Well, will you still lick me? I'm not really into fucking with this thing, but I do enjoy being licked and sucked. Will you try that for me, honey?"

Not sure what I was getting myself into, I said, "Yes baby. I don't know what to do though."

"I'll help you," she said. Melissa then leaned forward and placed a pillow beneath my head. She then brought her soft cock up, laid it on my chest, and asked me to touch it.

I reached up placed my fingers on her cock. As I did, she closed her eyes. I then began to slowly run my fingers up and down her cock and it started to stiffen a little. Melissa was about 4 inches soft, but was quickly approaching 5 or 6 inches as I touched her. I heard little moans from her and she said, "That feels so good."

I kept rubbing her cock, and as it got fully stiff, she began to move her hips a little. The head began to pop up a little and then down and she moved. Melissa then moved a little closer so that her cock was only a few inches from my mouth. With the pillow stuffed fully under my neck, my chin was basically on my chest.

I continued to rub her, and as I did, I noticed a large bubble of wetness at the tip of her cock. Melissa was definitely enjoying what I was doing. She kept her eyes closed, but the moans became a little louder as she let me know how good it felt.

After a few moments, Melissa moved her hips a little further forward so that the tip of her cock was essentially at my lips. Her pre-cum was even larger now and then she asked, "Will you lick it, honey?"

I parted my lips at this request and stuck out my tongue a little. Her pre-cum coated the tip of my tongue and I brought it back in. The taste wasn't actually bad. It was just a sweet tasting fluid. I stuck my tongue out again and this time Melissa slid a little forward again, pushing the head of her cock inside my lips.

I opened my mouth a little further and she slide forward again. Half of her cock was in my mouth. I closed my lips around it, and as she slowly pulled out, I ran my tongue over the head as she had done to me. This seemed easy enough. She then moved forward and backward slowly, and I repeated the maneuver with my tongue. Apparently I was doing the right thing, because her moans definitely got louder.

After a few minutes of Melissa slowly fucking my mouth, she began to quicken the pace a little. Her cock was rock hard and seemed like a hundred degrees. As she thrust forward, more of her cock seemed to fill my mouth. I relaxed my jaw and let her fuck me harder while trying not to gag.

"Oh!...umf....ugh," she moaned. "I want to cum in your mouth. Will you let me cum, baby?" she half-whispered and half-groaned.

With my mouth full of her raging cock, I motioned with my eyes it was OK. I didn't know what to do. What was I going to do when she came? Should I try and swallow? Should I try and let it run out of my mouth? What if she thought that was rude?

Melissa's pace continued and I felt her balls slapping against my chin. I could see it in her eyes she was getting close, and then it happened. Melissa let out a long moan and pulled her cock part way out of my mouth so that I wouldn't choke. I then felt jism after jism flood my mouth with her hot cum. Melissa kept her cock steady and I swallowed as much as I could, but some of it ran down my face and neck.

Her cum tasted sweeter than I thought it would taste and actually wasn't that bad. I couldn't believe I was even thinking that it tasted good, but it did. Melissa wasn't salty at all like they say some men are.

When Melissa recovered, she came back down to kiss me. "That was wonderful!" she said. "Do you still want to get engaged? Do you still love me?"

"As I said before, nothing would make me leave you. I do still love you, more than ever, and I still want to be engaged if you will have me."

Melissa got a huge smile on her face, and then leaned forward to kiss me. She kissed me deeply, tasting her own cum. After awhile, she reached back and touched my cock. It was rock hard again, and then she sat back and lowered herself onto my cock.

We fucked for hours it seemed, with me cuming in her ass once and then her mouth again. I also gave her a blowjob and ate her sweet-tasting cum one more time before we went to sleep. I know it's crazy, but Melissa having a cock just didn't matter. She was the same cute and fun person as before and her cock didn't change that. And I think I love her more now that I know.

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AnonymousAnonymous7 months ago

Fantastic story a great couple and maybe they'll end up being married They can always adopt a couple of babies and she can breastfeed the babies

Ladyboyworship42Ladyboyworship42about 2 years ago

A romantic story. It's warms my heart to read it but pains it at the same time. This is the type of love with a transsexuals I've longed for all my life.

triffle64triffle64about 2 years ago

A lovely little story that I enjoyed very much.

HardfordiverseHardfordiverseabout 2 years ago

I really enjoyed this story- thank you.

Synthia44Synthia44almost 3 years ago

Aa crossdresser I found your story extremely hot and well written. I wish that I could meet someone like that that would love me as I am not for what I have between my legs. Very well written story.

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